winter trips near chicago

15 Best Winter Road Trips from Chicago

Chicago is a fantastic city, known for its stunning lakeside location, the Magnificent Mile, and its world-class museums and galleries. However, it's also famous for its harsh winters, so there might be times you want to head out of the city during the coldest months of the year.

Whether you want to enjoy the winter weather or escape from it, a winter road trip from Chicago can mean hitting the slopes at a ski resort, viewing iconic landmarks, taking a festive shopping trip or relaxing in the winter sun in the Southern states.

Whatever kind of winter road trip you're interested in, we've put together some of the key facts for a whole host of fabulous destinations. Keep reading to find out where you could go, how to get there, and our pick of what's waiting for you when you arrive.

Best winter road trips from Chicago: a quick overview

Single-day trips (under 3 hours each way).

Snow in the city often isn't much fun, so head out to one of the mountains or lakes for a one-day road trip that lets you enjoy the winter weather at its best.

If you're thinking of setting off on a road trip from Chicago in another season, check out our ultimate guide for Best Road Trips from Chicago for ideas and inspiration.

1. Lake Geneva, Wisconsin

1 hour 50 mins from Chicago (80 miles)

Why you should visit: The shortest trip on the list, Lake Geneva makes a great weekend getaway due to the short driving time, plus the area is perfectly set up for visitors to enjoy the winter weather.

There's a real variety of activities to enjoy here – take to the snow for an active day outside, then relax at a beautiful spa. This popular vacation town is also less crowded in winter compared to the summer months.

How to get there: Head north on I-90 out of Chicago then join I-94. After around an hour, exit at Kenosha and pick up WI-50 west which will take you to Geneva.

Our highlights: Roll back 100 years and one of the biggest draws of Lake Geneva, WI, wasn't its snow, but the ice! Lake ice was harvested and taken to nearby towns and cities - it was big business here as late as the 1940s.

Through the rest of the season, winter sports fans will love to ski at Wilmot Mountain, a popular ski resort with over 20 ski runs suitable for a wide range of abilities. Or explore the wintery wilderness of Kishwauketoe Nature Conservancy - you can rent snowshoes if you don't have your own.

Back in town, the Ice Castles at Geneva National Resort & Club are a must-see. Ice sculptors spend nearly 2 months creating spectacular icy towers and turrets which are especially beautiful when they're illuminated at night.

Bonus: Early in February Lake Geneva's Winterfest bursts into action, with an ice sculpting competition and snow races!

Our travel tips: Book in advance if you're visiting Winterfest, as the town gets really busy.

2. Madison, Wisconsin

2 hours 40 minutes from Chicago (150 miles)

Why you should visit: Wisconsin's state capital has all the cultural and foodie delights that you'd expect in a big city, with added snow that opens up a whole range of other activities to enjoy.

Within a short distance of the city you can ski, skate, snow tube and sled, sometimes with beautiful views across Lake Mendota.

How to get there: This is a really simple trip – just follow I-90 all the way from Chicago.

Our highlights: Just outside the city at Cascade Mountain and Devils Head Resort you'll find some exhilarating downhill skiing as well as snowtubing and sledding. It's the perfect way to enjoy the snowy conditions, and there are ski runs here to suit many different abilities.

When it's time to warm up, head back into town to Old Sugar Distillery, a small local spirits producer, for a warming taster.

While you're in town you can take a magical snowy hike through the trees at Madison Arboretum, then round off your day with outdoor dining - several Madison restaurants have heated outdoor domes so you can enjoy snowy views while dining al fresco.

Bonus: After Christmas, a free maze is built on the lake shore out of the branches of discarded Christmas trees, a custom that has become firmly cemented in Madison's holiday traditions now.

Our travel tips: Check ahead for dates of candle-lit snowshoe trails across the city. They don't run every day, but when they do they're really magical.

3. Elkhart Lake, Wisconsin

2 hours 50 minutes from Chicago (150 miles)

Why you should visit: This beautiful little lakeside town hosts a magical Christmas market every year. It's also a great place to enjoy fabulous snow-based activities - the temperature usually sits around freezing and the area experiences heavy snowfall, so conditions are perfect.

How to get there: Follow I-90/I-94 north out of Chicago, then continue north on I-94 when the interstate divides. In Milwaukee, switch onto I-43 and continue north, before leaving the interstate just after Saukville. Then, follow WI-57 towards Plymouth, from where you'll pick up WI-67 to Elkhart Lake.

Our highlights: For many visitors, the main draw is the Olde World Christmas Market, a 10-day festive spectacular bringing together Czech, German and Russian Christmas traditions. It's a great way to spend time with friends, get into the festive mood, as well as to find some unique Christmas gifts.

If you're visiting at other times during the winter, there's still plenty to do in Elkhart Lake. The lake freezes over right through the winter, so you can head out with a guide for a unique ice-fishing experience.

Also, although this isn't a ski destination like some of the other trips, you can still enjoy some winter sports in Elkhart Lake. Go snowshoeing at Quit Qui Oc golf course or ice skate at June Vollrath Park.

Alternatively, if you'd prefer to just relax and unwind, maybe after a tour round the Christmas market or some time on the ice rink, head to the luxurious Aspira Spa to round off your trip.

If you're wondering how the town got its name, it's as simple as it sounds – it's because the lake is shaped like an Elk's heart.

Our travel tips: The town will be extremely busy while the Christmas market is running, so book accommodation and any special activities well in advance.

4. Grand Rapids, Michigan

2 hours 50 minutes from Chicago (180 miles)

Why you should visit: From January to March the town hosts the World of Winter Festival, which sees dozens of huge ice sculptures on display and special events held across the town.

The World of Winter Festival is the perfect post-holiday pick-me-up - the ideal way to brighten up the dark, cold months after Christmas. Or if you're here a little earlier in winter, you can get yourself into the holiday spirit with a snowy visit to the Sculpture Gardens or enjoy some exhilarating winter sports.

How to get there: Head east out of Chicago on I-90, keeping Lake Michigan on your left, then continue on I-94 as far as Lake Joseph. From here, follow I-196 further around the lake shore. It eventually turns inland to take you right to Grand Rapids.

Our highlights: The World of Winter Festival usually starts in the first week of January, and as well as ice sculptures you can see interactive installations from artists all over the world, with walking tours taking you through some of the outdoor art highlights.

The festival also hosts many fun events. These change year on year, but in the past have included things like silent disco, outdoor musical performances, and storytelling to mark Native American traditions or Chinese New Year.

If you're in Grand Rapids earlier in the season, you can enjoy some great skiing at Cannonsburg Ski Area. It will satisfy a wide range of abilities, and you can also try out snow tubing and snowshoeing here.

If your time is limited, take your sled and enjoy a free downhill ride at one of the several hilly public parks in the city.

For a more magical festive feel, head to Frederick Meijer Sculpture Gardens. This park is illuminated with amazing twinkling lights all through the holiday period and is a really popular local attraction. Then, for a unique and romantic end to your trip, you can even take a horse-drawn sleigh ride through the city.

Bonus: As well as being known for its winter sports, Grand Rapids is famous for its many craft breweries - in fact, it's been given the title of Beer City USA! So if time allows on your trip, you might like to tour a brewery or two or try some of the locally produced beers.

Our travel tips: You don't have to have your own equipment to enjoy skating, snowshoeing or skiing – it's available to rent at many of the attractions.

If you're coming for the World of Winter Festival, remember to wrap up warm. Many of the events and installations are outdoors, so, this being Michigan, chances are you'll be enjoying them in the snow.

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Weekend trips (3-6 hours each way)

As you'd expect, with much of the Midwest sitting under snow through the winter, the weekend trips you can take from Chicago all have a winter sports element to them.

So, pack up your skis and look out for your skates - but don't worry if you're not the biggest fan of the slopes, since you'll also find great restaurants, beautiful views and stunning spas at these weekend destinations.

5. Muskegon, Michigan

3 hours 20 minutes from Chicago (190 miles)

Why you should visit: As you'd expect in a town that sees significant snowfall from December to February, you can enjoy a range of winter sports. A particular highlight in Muskegon is its Luge track, which is open to the public.

There are only 3 other Luge tracks in the whole of the United States, so if you've always fancied trying out this exhilarating sport, this is probably your best chance.

How to get there: Similar to the Grand Rapids trip, follow I-90 then I-94 east out of Chicago as far as St Joseph. Then join I-196 and follow it north along the lake shore until you reach Holland. From here, turn onto Route 31 which takes you on to Muskegon.

Our highlights: As you'd expect, the main draw of Muskegon in winter is Muskegon Luge Adventure Sports Park. As well as sliding the high-speed downhill ice track, you can enjoy cross-country and downhill skiing, snowshoeing, and ice skating at the park.

Back in town you'll get beautiful winter views over icy Lake Michigan. Wrap up warm and walk out towards Muskegon South Breakwater Lighthouse – a really stunning sight – or take a walk on the lake's frozen beaches. If you're feeling active, there are places where you can sled on the frozen sand dunes.

Staying by the lake, seeing as the water freezes over, you can go ice fishing here with a guide, who can provide all the equipment you need if you don't have your own.

It's not all about the outdoors though. Muskegon Farmers Market operates indoors on Saturdays through the winter so you can warm up and stock up on some fabulous local produce.

Olympian Mark Grimmette trained on the Luge track here when he was young and went on to compete at five Winter Olympic Games, winning medals at two of them. The track is open to kids as young as 8 so bring the whole family and see if any of them catch the sliding bug.

Our travel tips: Visit the Luge in the evenings and you can warm up by a bonfire after your slide down the track. We'd recommend booking ahead to guarantee your entry, especially if you're visiting at busy times,.

You won't need any previous experience or equipment, as your entrance to the track includes a lesson and all the equipment you'll need to enjoy your visit safely.

6. Granite Peak Ski Area, Wisconsin

4 hours 30 minutes from Chicago (280 miles)

Why you should visit: As its name suggests, Granite Peak is a fabulous and long-established ski destination with some top-class runs and luxurious resort choices.

The biggest ski area in the state is perfectly set up for skiers, with fast lifts and dozens of trails to follow. You can easily fill a weekend here with fun and varied runs.

How to get there: Follow I-90 west out of Chicago, passing Rockford and Madison. Then, shortly after crossing the Wisconsin River, turn onto I-39 and follow it north to Granite Peak Ski Area.

Our highlights: Granite Mountain is one of the oldest ski resorts in the United States, and it's been at the forefront of innovation in the skiing industry. It was an early adopter of snowmaking technology in the 1950s.

Two different types of ski lifts were invented here - so when you ski here in modern times you'll be following the lead of some of the country's ski pioneers.

With fast lifts, extensive ski runs and stunning views, you'll probably want to spend most of your time here on the slopes. Rib Mountain, part of the ski area here, is Wisconsin's tallest mountain so you'll find plenty of downhill runs here to suit all abilities.

In Wasau, the nearest town to Granite Peak, there are some great food and drink options for the essential apres-ski part of the day! Visit in early February when the Winter Carnival comes to town and you can see firework displays or catch a fun ride on one of the resort's snow groomers.

When you're ready to head into the warm, make your way to Leigh Yawkey Woodson Art Museum. This award-winning, community-focused gallery always has something new to see, and with sculptures and exhibits inspired by nature, it makes the perfect complement to a day enjoying the views out on the mountain.

Our travel tips: This is a really popular ski area, and lift passes can sell out during the busiest periods. It makes sense to book ahead if you're planning on visiting between Christmas day and New Year, or weekends during January and February.

7. Boyne Mountain Resort, Michigan

5 hours 40 minutes from Chicago (350 miles)

Why you should visit: This is a year-round resort, but with 140 inches of snow, it comes into its own during winter. The extensive and varied ski slopes here are great for a wide range of skiing abilities.

This is the place to come for a great resort experience, with lodges, bars and of course, slopes, all in one place.

How to get there: Follow the interstate east out of Chicago and then continue north, keeping Lake Michigan on your left. After Grand Rapids, turn onto Route 131 and continue north past Big Rapids and Cadillac, until you reach Boyne Mountain.

Our highlights: Boyne Mountain is primarily a ski resort, so take to the slopes and explore more than 415 acres of ski runs. You can also snowshoe, tube or skate if you want a break from the slopes.

If you want to strike out a little further and explore, you can go horseback riding or cross-country skiing through the woodlands or try out snow biking for something new.

For a really exhilarating ride, fly right above the snow on one of the 9 ziplines. These will carry you up to a quarter of a mile across the resort's valleys, giving you a bird's eye view of your stunning surroundings.

For the perfect post-ski wind down, visit the Spa at Boyne Mountain before you head home. Book a fantastic treatment or simply hang out in the sauna, steam room or heated outdoor pool to enjoy the mountain vibes from a different angle.

Our travel tips: Equipment can be rented at this resort but arrive early on weekends or holidays as it's first come, first served. It's a popular place to visit, so book lift passes in advance if you know when you're traveling. If you're able to visit mid-week, you'll probably find the slopes are quieter.

Longer trips (Over 6 hours each way)

Whether you're looking for a festive shopping experience to ease you into the holiday mood, or a snowbird heading south for the winter, there are plenty of fabulous longer road trips that start out from Chicago.

8. Niagara Falls and Niagara-on-the-Lake, New York

8 hours 20 minutes from Chicago (550 miles)

Why you should visit: Seeing the famous falls cascading through the snowy ground is a truly magical experience – and one that's different from any other trip you might take.

Head across the border on this road trip to see the falls from a different perspective, or visit the fabulous wineries of Niagara-on-the-Lake. Canada produces a significant proportion of the world's Icewine, a dessert wine created from grapes left on the vine to freeze before being harvested.

Seeing the falls in winter is a magical experience, with massive icicles and undulating snow drifts surrounding the famous vistas. As well as being beautiful, the crowds that flock to Niagara Falls are slightly less during winter.

How to get there: Head east out of Chicago and join Interstate 90, then just keep going! The same road takes you right across Indiana and Ohio then along the whole length of Lake Erie, before you finally turn onto NY-5 through Buffalo around 5 miles before you reach your destination.

If you want to head across the border to visit Niagara-on-the-Lake make sure to pack the required travel documentation, and allow extra time to make the border crossing, especially if you're heading across Rainbow International Bridge.

Our highlights: The highlight of most people's visit to Niagara Falls is to see the mighty waterfalls up close, but if you visit in winter you can also marvel at the massive icicles that form right by the viewing platform on the Journey Behind the Falls. For amazing views of the snow-covered landscape, head up the Skylon Tower.

At night, you can see the falls lit up in spectacular illuminations as part of the Winter Festival of Lights. Then head quickly back into the warmth of your hotel to warm up. Several of the hotels in town have excellent in-house spas, so you can treat yourself to some relaxation time during your trip.

If you're crossing over the Canadian border to visit Niagara-on-the-Lake, the Icewine vineyards and wineries are probably the first thing that will get your attention. The long rows of vines stand out proudly in the snow and make a beautiful backdrop while you're learning about Icewine production or, more importantly, tasting a glass or two.

NOTL is also a really charming little town, and while you're here you might like to take a horse-drawn carriage ride through its historic streets - a wonderfully atmospheric way to travel through the snow-covered streets.

Bonus: Right through January you can enjoy the Icewine Festival, which celebrates this delicious local tipple. There's a real art to making Icewine and the conditions have to be just right to freeze the grapes for long enough on the vine.

This means you probably won't see the grape harvest unless you're out in the vineyards at night - pickers tend to work by hand to make sure of the most perfect harvest possible. All things considered, it's easy to see why Niagara-on-the-Lake's Icewine is such a special product to try during your visit.

Our travel tips: Some of the outdoor activities that Niagara Falls is famous for, notably the Maid of the Mist boat cruise, do not operate in winter, but as we've identified, there are plenty of other ways to enjoy views out across the falls.

Note that to enjoy all the attractions Niagara Falls has to offer, you might need to factor in crossing the US/Canada border so make sure you have any paperwork you need (dependent on nationality).

READ MORE - Road Trip from Chicago to Niagara Falls

9. Toronto, Canada

8 hours 40 minutes from Chicago (530 miles)

Why you should visit: With festive lights, winter markets, a good chance of snow, and plenty of big city attractions, Toronto is a picture-perfect winter city trip . Located right by Lake Ontario, you can enjoy frosty views out across the water, then head back into the city to indulge yourself in some culture or plain old festive cheer.

It's the perfect place for a romantic getaway - wrap up warm and enjoy snowy views over the beautiful city and lake before warming up with a hot chocolate and a loop or two around an outdoor ice rink.

How to get there: Follow I-90 out of the city then pick up I-94 and head east towards Detroit.

After crossing the border into Canada, the road becomes ON-401. It runs parallel to Lake Erie, so if you have a little longer to make your trip then you might like to pause along the way to admire views across the lake.

Just after London, the road merges with ON-403, which will take you right into the center of Toronto.

Our highlights: Toronto is a vibrant cultural melting pot, so when you spend time in the city you'll be able to enjoy influences on food, art and recreation from all over the world.

Less than half of Toronto's residents were born in Canada, making for a varied and welcoming city that's the perfect place to head to on a road trip.

For added romantic charm, put your skates on and have laps on one of the city's many ice rinks - there are over 50 to choose from. The rinks are super-festive in the run up to the holidays, and you can relax with a hot chocolate or a local craft beer afterwards.

If you're not planning a trip until after Christmas, you'll be able to visit the Toronto Light Festival, when fabulous installations brighten up the city through the cold winter nights. Check ahead to find details of live performances and special events that are taking place.

If it's your first time in Toronto, you'll probably want to see some of the city's sights while you're in town too. Head up the CN Tower for great views of the city and Lake Ontario, which is particularly stunning when it starts to freeze over through the winter.

Then warm up in one of the city's fantastic museums, including the Royal Ontario Museum where you'll find a fascinating and diverse collection.

Bonus: If you're here before the holidays, get into the festive spirit at the Distillery District Christmas Market, which runs from mid-November until New Year. It's a great way to experience this historic part of the city, full of character.

Our travel tips: Although temperatures are at or below freezing through most of the winter, you're not always guaranteed snow in Toronto, so be prepared that you might miss out on the insta-perfect images of this particular winter road trip.

As you can see, there are still plenty of wintery attractions to enjoy in the city, just wrap up warm and see where your trip takes you.

READ MORE - Road Trip from Chicago to Toronto

10. Washington, DC

11 hours 10 minutes from Chicago (700 miles)

Why you should visit: You can see the Nation's Christmas Tree, a century-old tradition in the city - it's illuminated from early December in a popular ceremony that for many marks the start of the holiday season.

You can also enjoy a number of holiday markets, to really get you into the festive spirit. You have a few to choose from, including the outdoor Downtown DC Holiday Market, the Swedish Christmas Bazaar in Georgetown, and the Heurich House Museum Christkindlmarkt.

As well as all the holiday attractions and the chance to see some of the world-famous monuments beautifully surrounded by snow, the crowds at the city's museums are likely to be quieter during the winter.

How to get there: Follow I-90 out of Chicago and east towards Cleveland. Then, join I-80 and follow it around the south of Cleveland before switching onto I-76 and continuing southeast past Pittsburgh.

After passing New Baltimore and Everett, change onto I-70 and continue on through the Appalachians before joining I-270 at Frederick and following it right into the center of Washington DC.

Our highlights: The nation's capital is a fantastic place to visit during the holiday period. As well as the festive markets that take place across the city, where you can admire beautiful decorations and gifts or enjoy some fabulous food and drink, you can take in a carol concert at the National Cathedral.

Afterwards, take some time to admire the cathedral's architecture - and see if you can spot the Darth Vader gargoyle.

Back outdoors, visit DC's largest outdoor ice rink at Washington Harbor, for views out across the waterfront, or see the Holiday Boat Parade, which includes fireworks and live music as well as festively decorated boats parading down the Potomac River.

If you're visiting later in the season, check out Winter Restaurant Week. The event runs in late Jan or early Feb, and hundreds of the city's restaurants showcase their best meals at reasonable prices - the perfect way to brighten up a long, cold winter.

Don't forget to check out some of the Smithsonian museums too – they're free to enter so you can visit one or many, and enjoy some of the more popular sites without the crowds, especially if you're visiting after the holiday period.

Bonus: The capital hosts a fabulous Lunar New Year Parade in January or February depending on when the new year begins. The parade brings together dragons and lions dancing through DC's streets, as well as drummers, dance troupes and firecrackers - it's a real feast for the senses.

Our travel tips: Don't go to DC expecting reliable snowfall – daytime temperatures are milder than the more northern destinations (in the mid-40 degrees Fahrenheit and above), though it still gets pretty cold at night, and snow is likely but not guaranteed in January and February.

The key message is to wrap up warm and be prepared for whatever weather the city throws at you - pretty standard for DC!

READ MORE - Road Trip from Chicago to Washington DC

11. Philadelphia, Pennsylvania

11 hours 50 minutes from Chicago (760 miles)

Why you should visit: Pennsylvania combines the kind of winter fun you might expect, like sledding and skating, with some unique winter traditions.

Visitors and locals alike flock to the Macy's Light Show, running for over half a century, and the charming Dickens Village, also found at the store.

Plus, you can fill yourself with festive cheer with a visit to the traditional market at Love Park's Christmas Village, or a stroll through streets filled with fabulous Christmas lights.

How to get there: Follow I-90 east towards Cleveland, switching onto I-80 just before you reach the city. This leads you south to join I-76, which you'll then follow past Pittsburgh, all the way across Pennsylvania. The same road takes you right into Philadelphia

Our highlights: You can see all the historic gems of Philly decked out with lights and trees for the holiday season, and the city's beautiful riverside setting just adds to the magic.

As you make your way from Chicago to Philadelphia , make sure to fit in a visit to Bethlehem, PA, too. The whole town gets decked out in style for the holidays. Take a magical horse-drawn carriage ride, check out entries for the Gingerbread House competition, and enjoy endless festive lights.

Once you've arrived in Philadelphia, you can ice skate beside the Delaware River at Winterfest, then warm up with a hot chocolate - or something stronger - with a view out across Benjamin Franklin Bridge.

Then, check out the Christmas Village or the Made in Philadelphia Holiday Market. If you're looking for unique and often hand-made gifts for family and friends, you'll find plenty of choice here.

The city's popular Longwood Gardens is transformed with amazing lights and live music, so it makes a great place to spend some time after the sun goes down (which happens early in winter!)

If you're in Philadelphia towards the end of the holiday season, you'll be able to watch the Mummers' Parade on New Year's Day. Thousands of people in absolutely dazzling costumes parade through the city in a historic tradition.

Bonus: Macy's Christmas Light Show – another of the city's festive traditions – is a record breaker! It features more than 100,000 lights and is the largest pipe organ in the world.

Our travel tips: Timed tickets are needed for some of Philadelphia's winter attractions, including Longwood Gardens and Dickens Village.

READ MORE - Road Trip from Chicago to Philadelphia

12. New York, NY

12 hours 40 minutes from Chicago (800 miles)

Why you should visit: New York City puts on an amazing holiday display – from festive lights to Christmas trees and fabulous window displays throughout the city, all with a thick covering of snow. This road trip from Chicago to New York is truly nothing short of magical!

Plus, if you're in the market for some Christmas shopping you can take your pick of fabulous department stores, designer brands and boutique sellers.

Get into the festive spirit and enjoy the iconic holiday views of the city - if it feels familiar, it's probably because they've featured in so many films and TV shows over the years. You should definitely visit New York in winter so you can say you've experienced them all first-hand.

How to get there: Follow I-90 east across Indiana. Just before Cleveland, merge onto I-80 and follow this all the way across Ohio, Pennsylvania and New Jersey before crossing into Manhattan via George Washington Bridge.

Our highlights: There are so many memorable festive moments to fit into a winter trip to New York City that it's hard to know where to begin. Skate beneath the massive Christmas tree at the famous Rockefeller Ice Rink, before heading up to the Top of the Rock to take in the view of New York in the snow.

Take a carriage ride through Central Park, which is even more magical when there's snow on the ground. Or if you're feeling more active, there are sledding slopes in the park, too.

Of course, NYC is famous for its shops, so leave some space in your case for whatever gifts and treats you might pick up while you're in town. Head to Macy's, Bloomingdale's or Saks Fifth Avenue for wall-to-wall shopping opportunities, or take a walk along Fifth Avenue to indulge in designer brands.

Further afield, the city is packed full of other shopping districts, including the West Village, Bleeker Street, Union Square and the Meatpacking District to name just a few. Or if you're in town with romantic intentions, a stroll through the Diamond District might go down well.

For a different experience of New York in winter, skip the crowds and visit in January to enjoy the NYC Winter Jazz Fest or NYC Restaurant Week, where restaurants put on their best fare at affordable prices.

If you're traveling at this time of the year, you can also stop off at New Hope, PA, as you make your way from Chicago to New York City. Here you can join in with the 9-day Winter Festival (late January).

Galleries, restaurants, and local businesses come together to bring some warmth and cheer to the new year, with a legendary chili cook-off, Soup-A-Thon, and ice sculptures dotted around town.

Bonus: These days, you usually need to take a ferry across from Manhattan to Staten Island, but back in 1780, the entire harbor froze so hard that it was possible to walk all the way across the river.

Our travel tips: Parts of the city get extremely crowded in December, and accommodation prices rise accordingly. The first week of December is particularly busy, but many travelers report that the crowds and prices calm down a little mid-month.

If you'd like to learn more about the best areas to stay in NYC before you plan your trip, you can find our detailed area-by-area guide here .

READ MORE - Road Trip from Chicago to New York City

13. New Orleans, Louisiana

13 hours 40 minutes from Chicago (925 miles)

Why you should visit: Mild weather and weeks of flamboyant parades makes New Orleans the perfect contrast to snowy Chicago. The city is famous for Mardi Gras, which takes place in late February, but warm-up events actually start in January, so you can enjoy week after week of enjoyment.

As well as Mardi Gras, New Orleans is also a vibrant city where you can enjoy live music, fabulous food and warm winter weather - perhaps the closest you can get to a trip overseas without needing a passport!

How to get there: On this road trip , join I-57 and follow it south all the way to Cairo, on the Illinois/Missouri border. Then, soon after crossing the Mississippi River, change onto I-55 and follow it south.

As far as Nashville, I-55 runs parallel to the Mississippi before passing through Jackson. Continue along the interstate then, after skirting the west side of Lake Pontchartrain, merge onto I-10, which takes you into the center of New Orleans.

Our highlights: From Thanksgiving onwards, enjoy a Reveillon Dinner – a local tradition that now sees restaurants across the city offering seasonal Creole-inspired food all through December.

Also running from Thanksgiving right up to New Year's Day is Celebration in the Oaks. This after-dark spectacle sees City Park lit up with more than a million lights. Given the city's mild winter climate, it's the perfect place to end the day with a romantic stroll.

If you're in the city for Christmas itself, head out along River Road on Christmas Eve, where you'll see bonfires lit on the night of the 24th so that Papa Noel can find his way from Baton Rouge to New Orleans.

Once Christmas and New Year are behind you, the party season in New Orleans really gets going. From mid-January, you can see parades and events starting up, then the main event, Mardi Gras, starts on Shrove Tuesday and carries on for two weeks. Expect fabulous parades, live music and all-night parties.

You'll have seen pictures of the beautiful and elaborate masks that are such a feature of the Mardi Gras parades. But did you know that every single participant has to wear one?

That way, current and future visitors will be guaranteed the same fabulous experience of NOLA's longstanding and unique traditions.

Our travel tips: Although average temperatures sit around 60 degrees Fahrenheit in winter, they can drop much lower or rise as high as 80, so it's wise to pack for three seasons to be prepared for a winter trip here!

READ MORE - Road Trip from Chicago to New Orleans

14. Savannah, Georgia

15 hours 10 minutes from Chicago (960 miles)

Why you should visit: The weather stays mild all year round in Savannah, so it's a great place to come and escape the Midwest chill. You can enjoy spending time outside, take a walk along the river, or just relax in one of Savannah's beautiful squares - the polar opposite of a Chicago winter.

Don't worry about missing out on too much of that winter snow either - your drive will take you through the Appalachians so you can take in some stunning views as you make your way south to Georgia.

Savannah is a great place to visit all year round but come in winter to enjoy this fabulous city without the summer crowds or humidity.

How to get there: After heading east out of Chicago on I-90, turn south onto I-65 and continue through Indianapolis and Louisville.

At Louisville, change onto I-64 and follow it towards Lexington onto I-75 which takes you across into Tennessee. Then, take I-40 from Knoxville to Asheville then join I-26 south passing Spartanburg and Columbia.

This leads you eventually onto I-95, which you'll follow south to Savannah.

Our highlights: There might not be snow and ice on the ground, but Savannah manages to fill the holiday season with its very own brand of festive charm.

At Coastal Georgia Botanical Gardens, you can follow the beautiful light trail through the magical gardens, for example, or take a holiday trolley tour or boat trip to see the city decked out in festive finery while enjoying a wonderful warm cider.

Then, follow the Christmas Parade, which makes its way through the city's streets and squares in early December.

All through the winter, you can also enjoy the shops and restaurants on fabulous River Street, the perfect place to spend some time whether you're looking for gifts to take home or just something special for yourself.

The city was offered up to President Lincoln as a Christmas Gift during the Civil War. As Christmas gifts go, a whole city is one we wouldn't mind receiving!

Our travel tips: Winter weather in Savannah is changeable, but the year-round humidity can make even warm days feel chilly when you're outdoors for a while.

READ MORE - Road Trip from Chicago to Savannah

15. Orlando, Florida

17 hours 30 minutes from Chicago (1,130 miles)

Why you should visit: Orlando is known as a winter sun favorite – so pack your sun cream and enjoy some time outdoors.

The theme parks of Orlando are popular year-round, but during the winter you get to experience them all dressed up for the holiday season, and without the heat and humidity that can be a feature at other times of the year.

How to get there: Follow I-90 out of Chicago then merge onto US-41 at the southern tip of Lake Michigan and continue south past Terre Haute and Vincennes.

Just after crossing the Ohio River at Evansville, turn onto I-69, continuing south on I-169 where the interstates divide. After Hopkinsville, join I-24 and follow it through Nashville to Chattanooga, where you'll switch onto I-75 which runs all the way to Florida.

After Gainesville, join the Florida Turnpike which takes you the last stretch of the drive into Orlando.

Our highlights: Florida is the warmest part of the continental US through the winter - perfect for escaping the sub-zero temperatures of the Midwest on this road trip from Chicago to Orlando !

Visit the theme parks in their holiday finest – whether your first choice is Walt Disney World, Universal Orlando, SeaWorld or Legoland Florida, each one will be suitably festive with parades and events to match.

You can see Cinderella's Castle made even more magical at Walt Disney World, or visit EPCOT's International Festival of the Holidays to take a whistle-stop tour around the world's traditions.

One that stands out for its festive themes is the Grinch-mas Who-liday Special at Universal Islands of Adventure. And of course, the Wizarding World of Harry Potter comes into its own during the winter.

If you have time to head out of town, make your way to Tampa to see Christmas Town at Busch Gardens. You'll find yourself in a warm weather wonderland with trees, lights, skating and fireworks.

Outside of the theme parks, you can enjoy the Winter Park Christmas Parade, a long-standing Florida tradition, with dozens of troupes followed by Santa.

And if you're missing that traditional winter vibe, visit Now Snowing in Celebration, where frosty views meet the Florida sun – including hourly snow flurries.

Our travel tips: Pack layers, as even Florida can experience cooler days, but rest assured that with heated pools and plenty of daytime sunshine, you can enjoy yourself outdoors right through the winter.

READ MORE - Road Trip from Chicago to Orlando

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BEST Winter Getaways Near Chicago (2024 Guide)

The best winter weekend getaways near Chicago in 2024. From romantic getaways for couples to fun winter road trips for families and friends, there is something for everyone on this list.

Winter Getaways Near Chicago/ Road Trips from Chicago in Winter

Looking for the best winter getaways from Chicago? If you can’t fly somewhere warm and escape winter in Chicago , embrace the cold and snow and visit these incredible winter getaways near Chicago.

(And make sure to check out my  essential road trip packing list (with free printable pdf) to make sure you have all your road trip essentials before you go!)

Disclaimer: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. 

Lake Geneva, Wisconsin

Lake Geneva is a great winter getaway near Chicago. Located only about 90 minutes from downtown Chicago, it is close enough to visit on a long day trip from Chicago .

Visitors can go skiing, snowboarding and sledding at the The Mountain Top at Grand Geneva Resort. Wilmot Mountain, another skiing resort near Lake Geneva, also offers tubing.

Other winter outdoor activities in the area include snowshoeing, cross-country skiing as well as ice skating.

One of the best things to see in Lake Geneva in the winter is Winter Realms (formerly the ice castles), a unique frozen attraction. The man made ice castles are worth seeing both in the day and at night when they are lit by colored LED lights. Dates are announced about a week before their opening but the ice castles are usually open from mid-January to end of February. Read more about visiting the ice castles here .

A popular winter event in Lake Geneva is Winterfest (January 31 – February 4, 2024), a nine-day annual festival dedicated to art, winter, and fun. One of the highlights of Winterfest is watching teams of snow sculptors and artists compete in the U.S. National Snow Sculpting Championship.

Find more things to do in Lake Geneva in the winter here .

Stay: Grand Geneva Resort & Spa

Getting There: By Car: Lake Geneva is approximately 83 miles from Chicago

Elkhart Lake, Wisconsin

While Elkhart Lake is a great summer lake getaway, it is also worth visiting in the winter. Dog sledding, snowshoeing, skiing and carriage rides are some fun winter activities available in the area. Visitors can also explore The Ice Age Trail .

Schnee Days Winter Festival (January 26 – 28, 2024) is a weekend of winter fun and a celebration of snow, with various activities includding the SchneeLauf 5K run/walk, annual chili cook-off, and children’s games.

Find more things to do in Elkhart Lake in the winter here .

Stay: The Osthoff Resort

Getting There: By Car: Elkhart Lake is 150 miles from Chicago (about 2.5 hour drive)

Galena, Illinois

Galena is great winter weekend getaway whether on a romantic trip or traveling with kids. Galena is a charming and historic small town. A large portion of the city is listed on the National Register of Historic Places and there are many historical sights to explore including the Ulysses S. Grant Home, the Elihu B. Washburne House, Dowling House and the Old Market House. Visitors will also enjoy strolling on half-mile historic Main St. loaded with one-of-a-kind shops and restaurants.

In addition to exploring the historic town, visitors can go skiing or snowboarding at Chestnut Mountain Resort, which has 19 total ski runs and a 7-acre terrain park suitable for a variety of experience levels.

The Nordic Center at Eagle Ridge Resort offers many fun outdoor winter activities including outdoor ice skating on their 1.5-mile long pond, cross country skiing, snowshoeing trails, sledding and even skijoring (a cross between cross-country skiing and dog-sledding).

Visitors can also go hiking or snowshoeing through Casper Bluff Preserve, the Buehler Preserve and the Galena River Trail.

Winter events include: Chocolate Lovers Stroll (February 10, 2024), Big Nut & Little Nut Big Air Competition (March 2, 2024), and the Galena Whiskey Weekend Grand Tasting (March 9, 2024).

Winter Carnival at Eagle Ridge Resort & Spa is a popular annual outdoor winter celebration during President’s Day weekend (February 16-19, 2024) featuring all types of winter activities including Fire and Ice winter shows, ice turkey bowling, s’mores making, ice carving stations and an ice bar featuring marshmallow shots.

Find more things to do in Galena in the winter here .

Stay: Country Inn & Suites by Radisson

Getting There: By Car: 164 miles driving distance from Chicago

Dubuque, Iowa

Dubuque, Iowa’s oldest town, is located across the Mississippi River about 20 minutes from Galena, Illinois. With its historic architecture and hilly landscape, Dubuque becomes magical when covered with snow.

Go skiing and snowboarding at Sundown Mountain Resort, with 21 ski runs and two terrain parks. Go hiking, cross country skiing or snowshoeing on the trails at Mines of Spain or Swiss Valley Nature Preserve.

Every year, Dubuque celebrates the Winter Arts Snow Sculpting Festival (the State of Iowa’s Official Snow Sculpting Competition) in its downtown Washington Park. Typically held the 2nd full weekend in February, teams of professional, amateur, and collegiate artists transform snow into masterful works of art. (The winning team is offered the opportunity to represent the state of Iowa at the U.S. National Snow Sculpting Competition in Lake Geneva, WI the following year.)

Find more things to do in Dubuque in the winter here .

Stay: Hotel Julien Dubuque

Getting There: By Car: Dubuque is 178 miles from Chicago (just over a 3 hour drive)

Frankenmuth, Michigan

Frankenmuth is known for being Michigan’s Little Bavaria. It is also home to Bronner’s Christmas Wonderland , the world’s largest Christmas store, which is open year-round.

Frankenmuth is a Christmas getaway from Chicago with many things to do during the holiday season .

Other things to do in Frankenmuth during the winter include ice skating, cross country skiing at Heritage Park  and sledding at Memorial Park. Visitors than want to escape the cold can visit Frankenmuth Brewery and two of Michigan’s top indoor waterparks .

Don’t miss the annual Zehnder’s Snowfest (January 24-28, 2024), that includes one of the top snow and ice sculpting events, a fireworks display, petting zoo and children’s activities.

Stay: Bavarian Inn Lodge

Getting There: By Car: 298 miles (about a 4.5 hour drive) from Chicago

What are your favorite winter weekend getaway from Chicago ?

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25 Weekend Getaways Near Chicago

Midwest Living's experienced editors create best-in-class travel, lifestyle, food, home and garden content you won't find anywhere else. We're loudly, proudly Midwestern, and we're passionate about helping our audience explore and create through award-winning storytelling.

When you need a day trip from Chicago or a weekend getaway from the big city, you don't have to go far. These escapes—including Amish Country, Indiana; Galena, Illinois; and Lake Geneva, Wisconsin—are within a one- to three-hour drive and offer a variety of activities that will recharge your life.

Indiana Dunes: 54 miles southeast of Chicago

This stretch of Lake Michigan coastline offers wide sandy beaches, towering dunes, great birding, easy bike trails and interesting history. Head to neighboring Chesterton for creative burgers at the Octave Grill and a pleasant night at Dunes Walk Inn, a restored 1881 mansion.

Lake Geneva, Wisconsin: 80 miles northwest of Chicago

This resort town of 7,600 has draws for summer and winter. Hotels, resorts and restaurants hug the lakeshore. Most visitors loll on the beach or cruise the lake during summer, but you can also experience the warmth of its winter in January and February during the annual Winterfest .

Michigan's southwest shore: 70 to 150 miles east of Chicago

Towns like New Buffalo, St. Joseph, Benton Harbor, Holland, Saugatuck and Grand Haven provide pristine beaches, great shopping, lakeside restaurants and front-row view of sunsets over Lake Michigan. The most accessible section of this shore extends from the Indiana line 175 miles north to Ludington. How far you drive is up to you – each town has its own personality. Take a spin on the carousel at St. Joe, tour a working windmill in Holland or just stretch out on a beach - preferably with a view of a lighthouse.

Galena, Illinois: 163 miles west of Chicago

Shops and restaurants in century-old buildings have long attracted visitors to this town of 3,500. But take time to hike, cruise the river or ski the slopes, sip local wines, taste beer and ... do some shopping.

Mount Morris, Illinois: 100 miles northwest of Chicago

With its rolling terrain, state parks and preserves traversed by the mighty Rick and Mississippi rivers, plus biking and hiking trails crisscrossing the area, the Blackhawk Waterways region of northwest Illinois promises outdoor recreation bliss. The region also helped shape the childhood of our 40th president, whose boyhood home opens its doors to visitors.

Cedarburg, Wisconsin: 113 miles north of Chicago

A great weekend destination for both shoppers and history buffs, Cedarburg has a Main Street that's on the National Register of Historic Places and dozens of limestone buildings housing more than 70 boutiques, chocolate shops and restaurants. Explore the town's history at the General Store Museum and Kuhefuss House Museum, and admire handiwork at the Wisconsin Museum of Quilts and Fiber Arts .

Bloomington-Normal, Illinois: 130 miles southwest of Chicago

For theater-lovers, summertime means outdoor Shakespeare. But in downstate Illinois, that takes on a fresh new form. Want improv Shakespeare? Sing-along Shakespeare? Or just a performance of his classics? Starting in June, and running through mid-August, the Illinois Shakespeare Festival in Bloomington-Normal reveals its ode to the Bard. Other draws to the area: Bloomington's restored 1800s buildings house farm-to-table restaurants, shops and live-music venues. Inside the three-story courthouse, a museum highlights the area's historical treasures.

Madison, Wisconsin: 147 miles northwest of Chicago

This town embraces the quirky and classy in its arts, museums, shops, dining venues and outdoor activities. Even its farmers market is a Bohemian rhapsody of local produce, entertainment, art and political activism on the state capitol square. Wander the paths and trails at Olbrich Botanical Gardens or the University of Wisconsin Arboretum ; admire the art at Chazen Museum of Art or the Madison Museum of Contemporary Art ; take a leisurely cruise around Lake Mendota or Menona; and be sure to work up an appetite-Madison's 600-plus restaurants offer something for every taste.

Rockford, Illinois: 90 miles west of Chicago

Illinois' third-largest city spent years watching travelers whiz by on Interstate-90 on their way east to Chicago. Now, thanks to a revitalized downtown, an emerging foodie scene, new cultural attractions and beautiful public gardens, word is getting out: You'd be crazy not to stop. The tranquil Anderson Japanese Gardens is just one of the draws to the area.

Fox River Valley, Illinois: 60 miles west of Chicago

An hour west of Chicago's Loop, the Fox River provides a soothing backdrop to towns brimming with indulgent eats, stores housed in historical homes and posh places to stay. Three towns along the winding river offer restful diversions with a nod to history: Catch a household name playing at St. Charles' historical Arcada Theater, or just 3 miles south, explore Geneva's shopping district, where boutiques fill preserved storefronts. And just minutes from Oswego's charming Main Street-with brick-paved sidewalks-is a family-run winery.

Milwaukee: 93 miles north of Chicago

Art, music and food festivals fill the calendar, and the compact downtown has just as diverse offerings. Watch the Milwaukee Art Museum's striking Quadracci Pavilion open and close its "wings"; catch the Milwaukee Brewers in Miller Park ; tour the Pabst Mansion ; or take a simulated motorcycle ride at the Harley-Davidson Museum .

Amish Country, Indiana: 110 miles east of Chicago

In tiny Nappanee, an Amish man parks his buggy by a gas pump, a living metaphor for the way new and old coexist in northern Indiana. Some people come here for classic Amish Country : 31 kinds of pie at Das Dutchman Essenhaus , hand-sewn gifts and homemade jellies at Little Helpers Quilt Shop , treasure-hunting at the Shipshewana Flea Market . But towns like Goshen, Middlebury and Elkhart also are modern communities.

Champaign-Urbana: 140 miles south of Chicago

Great outdoors, grown-up eats and classic clubs make these two cultured cities especially appealing in the summer when University of Illinois students head home. Grab a cheesy bite of nostalgia at Papa Del's Pizza or enjoy more upscale fare at Miga ; take time to admire the works at Krannert Art Museum and Spurlock Museum ; go for a stroll at the University of Illinois arboretum or Allerton Park and Retreat Center .

Starved Rock State Park, Illinois: 100 miles southwest of Chicago

Starved Rock State Park is a remarkable pocket of land along the Illinois River that includes 18 sandstone canyons, 14 waterfalls; abundant wildlife and birds; Belle of the Rock paddleboat excursions; and guided hikes, special events and interpretive programs. Spend the night in rooms or cabins (and enjoy a hearty meal) at Starved Rock Lodge , built in the 1930s by the Civilian Conservation Corps. If you're up for more exploration, also visit neighboring Matthiessen State Park , where 5 miles of trails carve into the mile-long canyon, passing rocks, waterfalls and beautiful, sometimes dizzying, vantage points.

Zion, Illinois: 50 miles north of Chicago

Zion is located in Lake County , which bridges the gap between Chicago's Cook County and the Wisconsin border with family attractions and nature trails. The area is home to Illinois Beach State Park , Volo Auto Museum and The Chocolate Sanctuary . For more fun, be sure to visit Six Flags Great America .

South Bend, Indiana: 95 miles east of Chicago

Though it's home to the Fighting Irish, it's not all football in South Bend. The St. Joseph River provides a great place for water sports and serves as a sparkling backdrop for a weekend of shopping and dining in the hometown of the University of Notre Dame.

Turkey Run Inn, Indiana: 150 miles south of Chicago

Sitting on a rocking chair on a veranda at Indiana's Turkey Run State Park inn feels surprisingly like taking refuge deep in the forest. The only sounds? Wind rustling through the trees. Owls hooting. Squirrels chattering. Brooks babbling. Maybe that's why quiet types flock here-bird-watchers, hikers and history buffs eager to explore Parke County and its covered bridges.

Grand Rapids, Michigan: 175 miles northeast of Chicago

Inspiration flows on both sides of the Grand River, particularly near downtown . Grand Rapids' ArtPrize extravaganza every other fall is part art walk, part city tour and and entirely vacation-worthy. But there's plenty to see at other times of the year, too, including the Frederik Meijer Gardens and Sculpture Park , Frank Lloyd Wright's Meyer May House and the Gerald R. Ford Presidential Library and Museum .

Elkhart Lake, Wisconsin: 150 miles north of Chicago

Sun, sand and...race cars? Most people come here for quiet weekends of swimming, sunning, boating and water-skiing in the crystal-clear lake , but the legendary Road America course is popular with amateur racers and their fans. Nearby Kettle Moraine State Forest also offers outdoor rec of another type with trails for biking, hiking and running. Round out the weekend with a stay in one of the area resorts such as the Osthoff.

Lake Mills, Wisconsin: 125 miles northwest of Chicago

Famous for The Ephraim Pottery Studio and Gallery , a getaway to Lake Mills also offers plenty of outdoor recreation on Rock Lake, the Zeloski Marsh and the Glacial Drumlin Bike Trail, as well as a cozy Arts and Crafts style B&B. Snack on crackers and sip wine at Lewis Station Winery, and don't miss the old-fashioned James J. Chocolate Shop.

Glencoe, Illinois: 15 miles north of Chicago

Glencoe is one of the few cities bordering Chicago along Lake Michigan. The communities of the North Shore seem farther from the bustle of downtown, thanks to abundant green spaces, including the Chicago Botanic Garden . Make sure to visit to Grosse Point Lighthouse during sunset in Evanston and take a walk along the Green Bay Trail between Winnetka and Highland Park.

Apple River Canyon State Park, Illinois: 146 miles west of Chicago

Every day, hundreds of drivers speed past the turnoff on US-20 for Apple River Canyon State Park , bound for getaways in Galena. Those travelers admire the view from the car, not realizing that if they wanted a peek at one of the area's few remaining secrets, they should turn north on Canyon Park Road west of Stockton and drive for just 7 miles. The 297-acre Apple River Canyon State Park offers quiet amid the woods along Apple River. Hike the bluffs. Look for fossils. Listen for wildlife. Fish the river—and let the others head to Galena.

Beloit, Wisconsin: 96 miles northwest of Chicago

This area is famous for its supper clubs that serve nostalgia and hearty portions. It all goes down easily with an old-fashioned drink.

Midewin National Tallgrass Prairie: 60 miles southwest of Chicago

Experience landscape that once rolled across the Midwest like an ocean at this restored prairie. Spot birds, hear frogs, hike and bike, see wildflowers and unwind among the 19,000 acres at Midewin National Tallgrass Prairie.

Woodstock, Illinois: 60 miles northwest of Chicago

It's just a train ride from Chicago, but Woodstock feels anything but suburban. The historic town square (famously featured in Groundhog Day ) is adorable, with great home decor shops and a cozy bookstore. Come for the summer activities or the annual Groundhog Day Festival in early February.

7 Winter Weekend Getaways From Chicago To Visit This Frosty Season

Grab your winter puffer and wool hate, winter is officially headed our way—which means you'll need a winter getaway asap!

As the temperatures drop and the polar vortex begins to take over the city, Chicagoans will brave the frigid temperatures in their trusty black puffer coats while the unbearable wind slaps across their face. On the bright side, there’s endless fun to be had in the wintertime to combat those winter blues , from igloo dining to heading to an enclosed rooftop bar . However, if fleeing the city is more up your alley, we know a thing or two about the best winter weekend getaways from Chicago.

1. Lake Geneva, Wisconsin

Located an hour north of Chicago at the Illinois-Wisconsin border, it awaits a landscape of rolling hills and immaculate views . One of our favorite winter weekend getaways from Chicago, Lake Geneva, is lucky to have not one but two noteworthy skill hills to check out for skiing , snowboarding, and snow tubing .

You can also explore the magical Winter Realm, an open-air experience where you can explore ice volcanoes, igloos, tubing activities, mesmerizing ice sculpture s, ice slides, and ice thrones. So, whether you want to explore the winter magic, need a spa, or want to hit the slopes, there’s something for everyone!

📍 Distance from Chicago : 92.6 miles

🕐 Time from Chicago : 1 hr 35 min

2. Elkhart Lake, Wisconsin

Elkhart Lake is the perfect winter weekend getaway from Chicago. You can i ndulge in seasonal favorites at one of the many taverns and escape the cold with a spa day at Aspira Spa .

If you’re looking for an offbeat activity, l et the Captain take you out on the ice for five hours of ice fishing with all the necessary equipment. This includes heated shanties , poles, tackle, and bait—warm clothes and a Fishing License is all you need, which you can get there.

📍 Distance from Chicago : 149.8 miles

🕐 Time from Chicago : 2 hr 29 min

3. Grand Rapids, Michigan

Grand Rapids has everything from skiing and snowshoeing to stage shows and festivals. The Christkindl Markt at the Grand Rapids Downtown Market is a European-style Christmas Village lined with artisan gift and food vendors, live holiday entertainment, and festive family fun. It’s bound to become another of your family’s favorite winter traditions.

You can also experience and enjoy winter in a new way during the World of Winter Festival in downtown Grand Rapids. For free, you can see large-scale outdoor art installations and amazing ice sculptures, enjoy musical performances, play games, stroll the city, and more.

📍 Distance from Chicago : 177.6 miles

🕐 Time from Chicago : 2 hr 47 min

4. Toronto, Canada

How about a little trip outside the country? In Toronto, you can experience the magic of the holiday season with the much-loved Cavalcade of Lights at Nathan Phillips Square. Inspired by international lanterns, fire, light festivals, and winter solstice celebrations, Cavalcade of Lights is a free event that transforms City Hall and its surroundings into a dazzling wonderland.

Toronto’s award-winning winter art exhibit, Window Wonderland, returns to the Junction for its fourth consecutive year. The magical urban art walk will transform the Junction into a free outd oor art gallery.

📍 Distance from Chicago : 515.1 miles

🕐 Time from Chicago : 8 hr 15 min

5. Mackinac Island, Michigan

Known as a unique vacation spot with an old-timey atmosphere. Mackinac Island is a national treasure, home to historic Fort Mackinac , world-famous Mackinac Island fudge, and car-free streets full of horse-drawn carriages.

This ideal vacation spot and winter getaway from Chicago is a paradise of exploration with incredible natural landmarks, awe-inspiring sunrises, and unforgettable sunsets. In winter, you can head on the Mackinac Island Turtle Trek, a beautiful lantern-lit ski and snowshoeing trek . You’ll head through some of Mackinac Island’s natural winter wonderland.

📍 Distance from Chicago : 415 miles

🕐 Time from Chicago : 6 hr 30 min

6. Saugatuck, Michigan

Gaze in wonder at the ice-kissed lakeshore. Experience relaxation while exploring their tranquil woods and snow-covered dunes . Peruse the warmly lit boutiques and inspiring galleries next to their snowy sidewalks. Or capture the joy and spirit of the season with nostalgic activities like a horse-drawn sleigh ride.

📍 Distance from Chicago : 141.9 miles

🕐 Time from Chicago : 2 hr 13 min

7. Boyne Falls, Michigan

The small village of Boyne Falls is named for the falls on th e nearby Boyne River . Take a walk on the wild side of the “World’s Longest Timber-Towered Suspension Bridge” and take in the views from this architectural masterpiece. This is one of the ideal winter weekend getaways from Chicago because it has the ultimate playground for skiers. Head to the Boyne Falls Mountain Resort, where you can let loose across 415 skiable acres.

📍 Distance from Chicago : 346.5 miles

🕐 Time from Chicago: 5 hr 16 min

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Best Weekend Getaways From Chicago

By Nina Kokotas Hahn

All products featured on Condé Nast Traveler are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.

Chicagoans itching to travel right now should not underestimate the power of a great winter road trip, and not just because it may feel like the only safe option at the moment. In a break from the norm, we’ve found exciting places offering something fresh and surprising for the Midwest, making them well worth the drive. A fun, elegant cocktail experience, lakefront retreats that offer stunning views, snowy ski trips with plenty more to do off the slopes—it’s all available. Here are the best weekend getaways from Chicago .

(Editors note: Given the changing nature of the COVID-19 pandemic , the hours and accessibility of many venues are fluid and subject to change. Make sure to contact them before visiting.)

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.

LAKE FOREST, ILLINOIS

Distance from Chicago 33 miles

The Deer Path Inn

In less than 60 minutes by Metra or just over 30 minutes by car, find yourself feeling far from the city in this pretty Northshore town off of Lake Michigan. No doubt Lake Forest is fancy with its sprawling estates, Market Square, and upscale shops (check out the all-women-run Lake Forest Bookstore and Valentina boutique), and coveted waterfront views. Being here also puts you 20 minutes closer to the 385-acre Chicago Botanic Gardens , where the Japanese and dwarf confider gardens are especially sublime in winter.

Where to Stay

The main reason to go to Lake Forest now is a weekend away at the 57-room Deer Path Inn ( from $329 per night ), a fabulous, little-known gem that puts you in arm's reach of the shops and lake, and offers many experiences available only to guests. Opened in 1929 with the style of an authentic manor house, the elegant inn feels as storied and local as it does far-flung and English. Spacious, modern, and sophisticated rooms offer upscale amenities (think Frette linens and bathtubs that fill from the ceiling); recently, the inn began in-room delivery of its popular Afternoon Tea service, complete with a tower of tea sandwiches, petit fours, and tartelettes. Patio dining in the English Garden at Deer Path is scenic and doable in winter with heaters. Guests at the hotel can also reserve the inn’s hidden cellar for a new, private, and totally custom cocktail or wine tasting paired with dinner that's led by Deer Path’s fun and expert chief spirits officer, Jorge Centeno.

INDIANA DUNES NATIONAL PARK, IN

Distance from Chicago 49 miles

The dunes overlooking Lake Michigan at Indiana Dunes National Park

Drive just 60 minutes and find yourself surrounded by beauty in the 15,000-acre Indiana Dunes National Park , which packs in an astounding amount of botanical diversity thanks to its variety of lowlands, highlands, prairies, wetlands, forests, and Lake Michigan shoreline. Time your visit with cool winter conditions, when snow cloaks the park in white, and there’s a chance to see spectacular shelf ice formations on the water, not to mention you’ll get a far more secluded experience. Venture out on cross-country skis or snowshoes—the latter of which can be borrowed for free at the park’s Paul H. Douglas Center for Environmental Education. All of the park’s 50 miles of trails are available for winter activities, but opt for a one-mile loop or three-mile route on the Paul H. Douglas Trail, which takes you to the beach through a rolling black savannah, one of the rarest habitats in the country. Often confused with the national park, the two-acre Indiana Dunes State Park , immediately next door, is also open and admission is waived on weekdays in winter.

Nearby Chesterton offers a good location central to both parks, and interesting B&B’s are the way to go. Within walking distance to restaurants and shopping, Riley's Railhouse Bed & Breakfast ( from $140 a night ) is housed in a former New York Central style freight station and has rooms in real rail cars. The family-friendly DunesWalk Inn at the Furness Mansion ( from $125 a night—you can also rent the entire place out on Airbnb ) is another historic option that balances digs in an 1881 mansion with modern comfort, just a few minutes from the beach.

HARBOR COUNTRY, MI

Distance from Chicago 75 miles

A view of Lake Michigan from the Water's Edge house

Didn’t score a Michigan beach house last summer? Winter isn’t hot, but it’s a gorgeous and secluded time to experience the dramatic Lake Michigan coast from the comfort of a luxury beach home, most of which can be had now at low season rates. Take your pick of towns on the state’s south coast like Union Pier, New Buffalo, and little-known Harbert. Sans summer crowds, this is the time to stop at the harborside Stray Dog Bar & Grill . Even better, book an igloo for outdoor dining at small-batch Beer Church Brewing , try alfresco wine tastings at Round Barn Estate , or get takeout from Red Arrow Roadhouse (try the buffalo cauliflower and nachos) and locally made whiskey from the Journeyman Distillery to bring back home. As everyone does, give into the pull of the lovely Lake Michigan coast, where dune walks and sledding at Warren Dunes State Park should be high on your list.

Bluefish Vacation Rentals (from $100 a night ) is your best option for a well-curated assortment of homes throughout Harbor Country, plus the bonus concierge-like guidance of the local husband-and-wife team who run it, Jason and Erika Milovich. In winter, most of their homes can be had at low season rates and don’t require summer’s usual full week stay. The scenery can’t be beat in Harbert at three-bedroom Water’s Edge , a splurge-worthy find tucked into a forested bluff overlooking a private stretch of Lake Michigan shoreline; spend $750 a night in winter verses the nearly double rate of $1,429 a night in summer. Walk the beach and watch glacier-like ice form with the waves, warm up in the hot tub, and light a bonfire under starry winter skies framed by trees. Other notable options include the three-bedroom Harbor Time , new five-bedroom Darby Cottage with its massive showroom-worthy open kitchen, and new four-bedroom Lake Life that puts spectacular lake views right in your lap.

KOHLER, WISCONSIN

Distance from Chicago 149 miles

Mark Ellwood

Lydia Mansel

Harrison Pierce

One of the Kohler luxury Cabins

On a drive of just over two hours, cruise past Mars Cheese Castle in Kenosha (hit the brakes to load up on Wisconsin gold), and lakefront Milwaukee, on your way to Kohler. Popular in temperate months for its jaw-dropping golf courses, which regularly feature on the PGA Tour, Destination Kohler is a find in winter with fewer visitors, killer spa treatments at its Kohler Waters Spa, and invigorating outdoor adventures at its lesser-known River Wildlife preserve. Like Kohler’s golf courses, the 500-acre wilderness playground showcases the natural beauty of the landscape here. Try hikes and horseback rides through rolling trails, ice skating and curling at Winter Wonderland, guided trap shooting in a forest canyon, and brunch or hot toddies at River Wildlife Lodge, the preserve’s atmospheric log cabin outpost.

Options at the resort include classic hotel rooms at the 241-room American Club ( from $189 ), but four chic and splurge-worthy cabins (f rom $842 a night ) are the way to go, especially if you want privacy and space wrapped in some gorgeous nature. The two-bedroom Lake Cabin ( from $1009 a night )—one of two opened just last summer—positions you on a staggering bluff just above Lake Michigan. The beach is inaccessible from this rugged perch, but you won’t care with endless, ocean-like views from the back porch and firepit, and the sprawling evergreen forest at the front of the house that doubles as a wildlife crossing (watch for deer and wild turkeys). It’s all the more magical with a dusting of snow on the beach grass, a warm fire, and dinners inside your own beautiful kitchen—everything from tenderloin and ricotta gnocchi takeout from the new Taverne on Woodlake to whiskey pairings, curated Wisconsin cheese boards, and gourmet groceries delivered from Woodlake Market .

Distance from Chicago 164 miles

Downtown Galena

With rolling forested landscapes, an historic downtown on the Mississippi River, and the best (one of the only!) ski mountain in Illinois, Galena is as charming as ever in winter. Even the two-hour-and-45-minute drive sets the mood as flat highways turn to one-lane roads that climb gentle hills and weave through farmlands and woods, eventually dropping you into this once-thriving river port town. Stroll the downtown’s Main Street for a superb array of local shops and studios; new options include Galena Book & Paper , the Galena Spoon Company for handcrafted spoons and carving classes, and Scent Workshop , where you can learn French perfuming techniques. There are loads of restaurants and boozy options here, too; go for especially good take-home dining and cocktail kits from French-meets-German Fritz and Frites , Miss Kitty’s Grape Escape , and the drive-thru Galena Brewing Co . Downhill skiers won’t want to miss Chestnut Mountain Resort, just 15 minutes from the downtown, with 19 runs that race to a halt at the bank of the Mississippi River.

It’s a-okay to vape in the new guest-only “potting shed” outside the pretty five-bedroom Aldrich House , Illinois’ only cannabis-friendly bed and breakfast ( from $145 a night ). For something upscale and romantic, it’s hard to do better than the luxury six-suite Jail Hill Inn , set in a former jailhouse at the end of Main Street and serving a three-course breakfast ( from $345 a night ). Families settle in nicely at the stylish, condo-like Ulysses Suites ( from $214 a night ), while south of downtown on 6,800 acres of Galena Territory, Eagle Ridge Resort & Spa offers a robust nordic activities program and everything from simple hotel rooms to full homes ( from $99 a night ).

INDIANAPOLIS, IN

Distance from Chicago 185 miles

The Bottleworks Hotel in Indianapolis' Bottleworks District

Every worthwhile weekend getaway from Chicago isn’t a charming small town or lakeside retreat. For those who want some city culture that isn’t their own, Indy’s Bottlework’s District is calling. Stop in Merrillville for proper road trip junk food—fresh Indiana-made gummy bears—at Alabanese Confectionery Group on the three-hour drive south to Indy. Once there, head to the new 12-acre, mixed-use neighborhood that spans the north side of Mass Ave in downtown Indianapolis and brims with local indie shops in historic industrial buildings. Explore the mix of offerings at Circle City Industrial Complex , a 500,000 square-foot warehouse opened in the old Schwitzer car manufacturing facility, where you should check out newly opened SoChatti dairy-free chocolate tasting room and a class at Indy Fused Glass. Other new places worth a visit are Good Neighbor for fresh duds and the Living Room movie theater. For dinner, head out of the district for romantic outdoor dining in the new fireside greenhouse huts at Public Greens , a modern, community-driven restaurant that shares its profits to feed nearly 2,000 of Indy’s less fortunate youth every week.

Opened in December in what was formerly the world’s largest Coca Cola bottling plant, the 139-room Bottleworks Hotel ( from $249 a night ) is the stylish new anchor for the Bottleworks District. The industrial, art-deco-inspired hotel occupies the top two floors of the historic building, showing off a white terra-cotta exterior and brass-patterned doors. High-style rooms have velvet couches, loft ceilings, and terrazzo-tiled floors. Adjacent to the hotel, find more dining options at Garage Food Hall , Indy’s first food hall opened this month in the factory’s former garages, with nearly two dozen vendors serving everything from lobster rolls and poke to Pakistani-Indian fare and Brazilian steak.

BOYNE, MICHIGAN

Distance from Chicago 346 miles

A look down Boyne Mountain

Make your winter ski trip happen at Boyne Mountain Resort , one of the most exciting ski mountains within a reasonable drive of Chicago—five and a half hours, plus a one-hour time change. Rising up from the northern part of Michigan’s lower peninsula, the mountain offers 500 feet of vertical with 60 downhill trails for a range of skiers and riders, though the biggest perk of a visit here is the abundance of high-quality outdoor adventures that go beyond skiing. Rent a new sno-go ski bike and shred downhill runs, fat-tire bike on forest trails, zipline 50 feet in the air across the mountain, cross country ski or snowshoe on dedicated trails, ice skate or snow tube, and even dine outdoors in one of five igloos serving at Forty Acres Tavern. If you have a little extra time you can also tack on the 40-minute drive north to Boyne Highlands , the mountain’s sister resort, for even more challenging ski terrain plus the new “Enchanted Trail,” an illuminated two-mile trail for nighttime winter walks and snowshoeing. NOTE: Like other ski resorts around the country, both mountains are limiting capacity during the pandemic and booking lift tickets and gear rental in advance is recommended.

Spread out in one of the fully-equipped three- and four-bedroom Mountain Cabins that are part of the resort (f rom $607 per night ). Each is set in the woods with a hot tub on the deck, fully equipped for cooking your own meals, and offers ski-in/ski-out access. Some of the cozy one- and two-bedroom condos at the Village at Disciples Ridge also offer ski-in/ski-out access ( from $488 per night ). Pro tip: the best way to guarantee access to the slopes this season along with your accommodations is to book a “ Ski & Stay Package ,” which bundles lodging and lift together and lets you ski both resorts.

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24 Top Weekend Getaways From Chicago

From beaches to ballparks and trails to rails, explore top breaks from the Windy City.

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Hike along Michigan's Sleeping Bear Dunes National Seashore on your next weekend getaway from Chicago.

Known as the birthplace of the skyscraper, Chicago is home to award-winning restaurants , top sports teams and prized cultural treasures. But when you need a break from the excitement of the nation's third largest city, there are countless getaways within easy driving distance. You can explore rural Illinois or enjoy neighboring Indiana, Wisconsin, Iowa or Michigan all within a weekend. Whether you're planning a romantic getaway to a small-town bed-and-breakfast or a family-friendly trip to a water park resort, these nearby Midwest destinations will relieve the stress of big city life.

(Note: Some of the following activities, attractions and locations may be affected by the COVID-19 pandemic. New policies may be in place, including capacity restrictions, reservation requirements or mask mandates. Check with the Centers for Disease Control and Prevention, the U.S. Department of State and local tourism boards before traveling.)

Best Weekend Getaways from Chicago:

About two hours or less:, fox river valley, illinois, harbor country, michigan, st. joseph, michigan, milwaukee, wisconsin, south haven, michigan, starved rock state park, illinois, gurnee, illinois, wilmot mountain, wisconsin, lake geneva, wisconsin, grand geneva resort & spa, wisconsin, about three hours or less:, turkey run state park, indiana, the american club resort hotel, kohler, wisconsin, whistling straits golf course, sheboygan, wisconsin, saugatuck, michigan, wisconsin dells, wisconsin, about four hours or less:, parke county, indiana, galena, illinois, dubuque, iowa, and the field of dreams, ann arbor, michigan, madison, wisconsin, about five hours or less:, traverse city, michigan, louisville, kentucky, st. louis, missouri, a quick flight:, minneapolis – st. paul, minnesota.

Located along the picturesque Fox River on the western outskirts of Chicago lie the small towns that make up Illinois' Fox River Valley. Stretching from the village of Antioch in the north to Ottawa – the gateway to Starved Rock State Park – in the south, this area is an ideal daytrip from the Windy City. Go biking, hiking and cross-country skiing along the 32-mile Fox River Trail or rent a kayak for paddling on the Fox River. In addition to outdoor pursuits, unique cultural attractions abound, including Broadway productions and musical events in Aurora's historic and beautifully restored Paramount Theatre. Visitors rave about its exquisite decor and top-notch performances, applauding the Paramount for offering Broadway-caliber performances at Main Street prices. If you choose to overnight in the Fox River Valley, the Herrington Inn & Spa , which overlooks the Fox River in the small town of Geneva, would make for a romantic getaway.

New York has the Hamptons; Boston has Cape Cod . The summer playground for Chicagoans consists of eight glistening lakeshore towns dotting the coastline of southwest Michigan, collectively known as Harbor Country. Here you'll find beaches, orchards and plenty of outdoor activities. At the southern end of Harbor Country, just over the Michigan-Indiana state line and about 70 miles from Chicago's downtown loop, New Buffalo lures Chicagoans with its casual beach vibe and proximity. Families line up for burgers at The Stray Dog, but only adults can head up to the rooftop bar and patio. Patrons praise The Neighborhood Hotel Grand Beach for its modern design combined with cozy common areas, fire pits, ping pong tables and board games; they also appreciate the short walk to the beach and the heated pool.

[Read: The Top Things to Do in Michigan .]

Families will want to make the scenic 25-mile drive from New Buffalo north through the Harbor Country towns of Union Pier and Lakeside, past grand lakefront estates and bucolic farms, to St. Joseph, commonly called St. Joe's. The family-friendly Silver Beach Pizza is housed in St. Joe's former train depot, with diners saying it's well worth what can be a half hour wait for the amazing pizza. Across the street is the restored 1910 Silver Beach Carousel, a great option for passing the time while waiting for your table if you've got kids along. St. Joe's offers visitors the chance to step back in time with a beach, pedestrian-friendly downtown, boutiques and old-fashioned chocolate shops. One of St. Joe's more unique shops is Third Coast Surf, where you can rent a surfboard and sign up for surfing or sandboarding lessons. Not expecting a surf shop in the Midwest? Visitors are often surprised when they first see Lake Michigan, known to Midwesterners as the Third Coast: It resembles an ocean more than a lake.

Located about 80 miles north of Chicago on Lake Michigan is the Brew City of Milwaukee , which boasts more than 200 breweries, museums, festivals and the Harley-Davidson Museum . As this city is home of the Milwaukee Brewers baseball team, no trip is complete without getting a taste for Milwaukee's beer heritage. Visitors give Lakefront Brewery tours high marks for entertaining guides, extensive selection, riverfront views and its popular Beer Hall restaurant with live music on Fridays. Families will enjoy the lakefront museum campus, which includes the Discovery World science museum and Betty Brinn Children's Museum, while culture lovers can visit the architecturally stunning Milwaukee Art Museum when the building's "wings" open and close several times a day. Motorcycle enthusiasts will be in hog heaven at the modern steel-and-glass Harley Davidson Museum, which celebrates the machine invented in Milwaukee that's come to symbolize the freedom of America and the open road.

Winters are harsh, so summer is one endless celebration, with a multitude of neighborhood festivals, outdoor concerts and ethnic celebrations – check out German Fest at the end of July, honoring the city's largest immigrant group. Summer excitement reaches a crescendo at the end of June with Summerfest, the world's largest music festival. After a day of sightseeing or revelry, a top lodging choice is Milwaukee's stately grand dame, the historic Pfister Hotel , offering Gilded Age elegance alongside 21st-century amenities like a pool with panoramic city views and a popular top-floor cocktail bar.

[See more of Milwaukee:  Things to Do  | Hotels  |  Photos ]

South Haven is a fun-loving beach town with a population that swells in the summer – especially in August for the National Blueberry Festival, since this Michigan destination claims to be the blueberry capital of the U.S. About 110 miles from Chicago, you'll hear a lot of Jimmy Buffett playing in the bars and restaurants of this laid-back boating town where the harbors take center stage. Kick off your visit by learning about the area's rich Great Lakes boating history at the Michigan Maritime Museum.

Along with its seven public beaches – some of the best beaches in Michigan – and iconic red lighthouse, South Haven also has a pedestrian-friendly downtown filled with unique shops and restaurants. Climb aboard the stationary Idler Riverboat, where casual dining combines with world-class waterfront views. Clementine's is another local favorite, as is Captain Lou's, which serves fresh perch and live music on the weekends. For a romantic getaway, consider Inn at the Park, a bed-and-breakfast one block from Lake Michigan: Guests praise the beautiful decor and sumptuous breakfasts, using locally grown blueberries. Travelers also love Yelton Manor Boutique Hotel for its manicured gardens, spectacular sunset views of Lake Michigan and proximity to town.

Looking for an active adventure? Only about 100 miles southwest of Chicago, this wilderness known for its deep sandstone canyons and waterfalls is perfect for daytrips – though with 18 canyons to hike, there's plenty to keep you busy for a whole weekend. Walking along bluffs that lead to scenic lookouts over the Illinois River makes visitors feel immediately transported out of the flat Midwest heartland. Starved Rock State Park can be a weekend escape any time of year, but spectacular fall foliage makes it a favorite getaway for autumn in particular.

Starved Rock State Park has its own historic lodge with top-notch cabins , but kids may prefer going across the street to the family-friendly Grizzly Jack's Grand Bear Resort, with its massive water park, mini-golf, indoor arcade and Northwoods decor. Camp Aramoni is a great choice for a romantic getaway, with luxury glamping in safari tents outfitted with hardwood floors, air conditioning and heating, and full bathrooms with showers. Nightly stays include chef-prepared farm-to-table dinner and breakfast using produce grown in on-site gardens that guests are welcome to visit. End your day at Camp Aramoni's repurposed Airstream trailer that's been turned into a bar.

Looking for high-adrenaline family fun? About 35 miles north of Chicago, just south of the Wisconsin border, lies the village of Gurnee, home to the Six Flags Great America amusement park . Thrill-seekers will love the 17 heart-stopping roller coasters, but dozens of other rides mean you'll also find plenty for younger kids. Reluctant riders who want to steer away from high-speed coasters and intense drop rides can also enjoy the park's shows and other entertainment. On a hot day, plunge down steep waterslides or splash around the wave pool at Six Flags' 20-acre Hurricane Harbor water park. When it gets cold, a favorite local pastime is a stroll around Gurnee Mills, an outlet mall housing more than 170 stores.

Continue your Gurnee adventure with a stay at the Northwoods-themed Great Wolf Lodge, the most family-friendly hotel option in this destination. Guests say this water park resort makes even adults feel like kids again and rave about the endless family-friendly amenities, which include bowling, mini-golf, a ropes course and arcade – and, of course, the massive water park.

Since 1938 Wilmot Mountain has drawn visitors seeking wintertime leisure in the Midwest. About 25 miles northwest of Gurnee, just over Wisconsin's state line, Wilmot Mountain Ski Resort makes for a great cold-weather attraction when Six Flags is closed. The big-name Vail Resorts purchased Wisconsin's little ski hill in 2016 and rolled out plenty of upgrades, from improving terrain parks and snowmaking to adding chairlifts and elevating the dining experience. Enjoy winter sports over a variety of terrain at this alpine destination, whether you're looking to ski, snowboard or snow tube. There's no on-site lodging, but Gurnee's Great Wolf Lodge is still a relatively short drive away.

[Read: The Top Things to Do in Wisconsin .]

This Wisconsin resort city makes for an idyllic weekend or daytrip. About 70 miles northwest of Chicago, Lake Geneva is described as the " Newport of the Midwest" because of its opulent lakefront mansions. You can come surprisingly close to these impressive residences by ambling along the Geneva Lakeshore Path, a rustic 25-mile walkway that encircles the lake, cutting right through the backyards of magnificent mansions and second homes. Amazingly, there aren't any "No Trespassing" signs to scare away walkers; just beware the path is not intended for strollers, roller blades or bikes, since you'll have to maneuver past steps and other obstructions. When you've finished your stroll, a lakefront cruise is another fun way to enjoy this city. Visitors give Lake Geneva Cruise Line excellent reviews for being informative and entertaining. A variety of daily cruises are offered, but one of the most unique is the mail delivery cruise. As Lake Geneva is one of the few remaining places in the U.S. where mail is still delivered by boat, about 75 lakefront homes receive their U.S. mail service via boat – and passengers are invited to come along for the ride.

Consider a stay at the Abbey Resort, the only full-service resort directly on the shores of Lake Geneva, during a summer visit. This lodging option offers complimentary adult and kids bikes, ideal for use on the Lake Geneva Bike Path, which connects many of the resort town's amenities. The trail has five unique, color-coded segments, making it easy to find your way around. Things quiet down a bit in the fall, when the vibrant autumn colors set a serene scene.

[Read: The Best Midwest Vacations for Families .]

Tourists descend on Lake Geneva's charming downtown shops and restaurants in the summer, but the town has plenty to do year-round. One of the best winter attractions in this city is the Grand Geneva Resort & Spa , whose modest ski hill has three chair lifts, 20 runs and a terrain park. Grand Geneva Resort also has access to 5 miles of wooded trails for cross-country skiing and offers a limited number of ski rentals. Kids will love overnighting at Grand Geneva's family-friendly Timber Ridge Lodge and Waterpark for indoor aquatic fun while adults relax at the spa. Time your winter visit to coincide with Lake Geneva's Winterfest so you can observe one of the country's biggest snow sculpting competitions.

Turkey Run State Park is the crown jewel of Parke County and one of the Hoosier State's oldest and most popular state parks. Eleven trails ranging from a half-mile to 2 miles wind through rugged ravines surrounded by the park's signature sandstone cliffs – providing Midwest hiking at its best. Turkey Run Inn, a popular lodging option situated within the park, is appreciated by guests for its friendly staff and cozy atmosphere. There's an indoor pool and plenty of public sitting areas with fireplaces, whether you want to play a board game or read a book. Choose from rooms within the historic lodge or the adjacent cabins. Even if you don't stay at Turkey Run Inn, you can still enjoy its restaurant, The Narrows, which diners recommend for the catfish dinners as well as the fried biscuits and hot apple butter.

Most have never heard of this tiny town 140 miles north of Chicago, but Kohler is home to Wisconsin's only hotel to receive AAA's highest five diamond rating. The American Club Resort Hotel – part of the Destination Kohler Resort – is still owned by the family who built it: The Kohlers are best known for high-end plumbing and bathroom fixtures. The American Club's luxurious Kohler Waters Spa specializes in hydrotherapy, giving guests a chance to experience all the legendary bath and shower products Kohler is known for. Should you want to recreate that luxury spa experience in your own bathroom at home, a few steps away from the spa is the sleek, multistory Kohler Design Center, filled with model bathrooms and design ideas sure to give most of us bathroom envy. Amid your self-care ventures in Kohler, enjoy plenty of outdoor activities. Fall brings a boisterous bounty of color to this rural area, while winter experiences at The American Club include ice skating, curling, snowshoeing and cross-country skiing across miles of trails that wind through woodlands and meadows.

Ten miles from American Club Resort Hotel sits the Kohler-owned Whistling Straits Golf Course, which some golfers describe as reminiscent of the legendary Pebble Beach . Whistling Straits ranks among the top public courses in the country and has hosted 2021's Ryder Cup and three PGA championships. The two Pete Dye-designed courses at Whistling Straits offer stunning views of Lake Michigan or rolling green hills. Golfers will feel transported to Ireland's tranquil grassland or its rugged coastline as this course winds its way along the bluffs and dunes overlooking Lake Michigan.

It's easy to see why Saugatuck is one of the best places to visit in Michigan . Nicknamed the Art Coast of Michigan, this hip resort town about 130 miles from Chicago is stocked with galleries, boutiques, excellent dining and beaches. Perhaps surprisingly for a town of less than a thousand people, Saugatuck is also known for its lively nightlife and for being an LGBTQ-friendly destination. Take a seat at the counter of the century-old Saugatuck Drug Store and you'll get a taste of the town's more traditional side, served up via a classic malt or ice cream soda. Visitors are in for another nostalgia trip when you board the chain ferry: Operating since 1838, it claims to be the only remaining chain-driven ferry in the U.S., transporting passengers across the Kalamazoo River between downtown and Oval Beach. After disembarking on Oval Beach, active beachgoers love climbing the 302 steps to the top of Mount Baldhead – known as Mt. Baldy – and getting a bird's eye view of the area. Overlooking Lake Michigan, Saugatuck's Lake Shore Resort is applauded by patrons for its breathtaking views and many complimentary amenities, including bikes, kayaks, yoga and a heated pool.

About 190 miles northwest of Chicago is the ultimate Midwest family getaway: the "Waterpark Capital of the World." If traveling with kids to Wisconsin Dells, stay at one of the immensely popular water park resorts , such as the flagship property of Great Wolf Lodge. Guests appreciate the original Great Wolf Lodge for its signature Northwoods decor, endless amenities and the feeling of being in a tropical paradise year-round.

Beyond its myriad indoor and outdoor water parks, Wisconsin Dells boasts a wide variety of kid-friendly entertainment options, from zip lines to animal parks. Catch a performance at the Palace Theater, which offers everything from concerts to comedy shows to children's plays and Broadway-style productions; some theatergoers swear there isn't a bad seat in the house. More fun for the whole family can be found at the Rick Wilcox Magic Theater shows, which wow audiences with both humor and illusions that keep you guessing. Want to escape the indoor attractions for a natural one? Head over to Mirror Lake State Park for a scenic hike along a tranquil, no-wake lake set among sandstone bluffs. Pontoon boats, kayaks and stand-up paddleboards are available to rent here.

[Read: The Top Things to Do in Wisconsin Dells .]

Billing itself as the covered bridge capital of the world, Parke County, Indiana – about 160 miles south of Chicago – maintains 31 of these Instagram-worthy symbols of a bygone era. Visitors descend on the area every October for the Parke County Covered Bridges Festival, Indiana's largest annual festival. The popular biker bar Thirty Six Saloon is a family-friendly roadhouse in Rockville, the town where the popular fall festival is headquartered. Kids may be mesmerized by Thirty Six Saloon's vast collection of taxidermy, with animals from the region mounted throughout the restaurant. Diners compliment everything from the burgers and ribs to the fish sandwiches and unique decor. Another popular culinary option is the tenderloin sandwich at the Mecca Tavern in Mecca. Parke County's oldest tavern overlooks Mecca's historic schoolhouse and covered bridge. Locals and visitors alike say stopping by Wheelhouse Donuts is another must: This adorable bakery lets you design your own doughnut.

About 150 miles west of Chicago, in the northwest corner of Illinois, the charming Mississippi River town of Galena regularly makes national lists of best small towns . Its elegant dining, historic sites, quaint shops and bounty of bed-and-breakfasts make Galena an excellent choice for a romantic getaway. Because the glaciers that flattened most of the Midwest didn't reach here, the pastoral farmland is hillier, perfect for a Sunday drive. The 19th-century buildings in this old mining town have been painstakingly preserved, with 85% on the National Register of Historic Places – including the Ulysses S. Grant Home State Historic Site, a residence gifted to the nation's soon-to-be 18th president in 1865 by Galena citizens.

One memorable overnight option would be a stay at the former county jailhouse – now the luxurious Jail Hill Inn. For a more romantic atmosphere, the Goldmoor Inn is beloved by guests for its stunning views of the Mississippi River, in-room fireplaces and two-person hot tubs. Galena is gorgeous any time of year, with plenty of travelers drawn here during harvest time for apple and pumpkin picking amid the abundance of fall colors. Winter brings its own charm with shops along Main Street resembling something out of a Norman Rockwell painting. The small town also houses a popular old-school ski resort: Guests say Chestnut Mountain Resort's decor and amenities are a bit dated, but its 19 ski runs provide scenic views of the river below.

Head 170 hundred miles west of Chicago, cross the Mississippi River, and you'll be in Dubuque, Iowa. Get a feel for how important the river is here by visiting the National Mississippi River Museum and Aquarium, or take a ride on a riverboat for another scenic way to experience the Mississippi. Visitors give the Celebration Belle river cruise high marks for being fun, informative and affordable. Another must-see attraction is Fenelon Place Elevator, a steep funicular railway providing fabulous views of the surrounding area. History lives on at the elegant Hotel Julien Dubuque, which guests compliment for its charm and friendly service. Baseball fans will want to make the additional 25-mile drive west to the town of Dyersville to explore the Field of Dreams, one of the best tourist attractions in the U.S. Play on the baseball diamond and tour the home where the movie "Field of Dreams" was filmed.

About 230 miles northeast of Chicago, Ann Arbor is a quintessential college town, filled with independent bookstores and great live music. University of Michigan alumni are a proud bunch – and not just on game days, when they march clad in blue and yellow to what's known as The Big House, the largest sports stadium in the country. Ann Arbor also scores an A when it comes to food and culture. The world-class University of Michigan Museum of Art displays works by Picasso, Monet and Warhol. A few blocks away on Liberty Street is the edgier public art canvas known as Graffiti Alley, just steps from the historic Michigan Theater and State Theatre, which delight visitors with film screenings, festivals and live music throughout the year (as long as you follow the theaters' COVID-19 regulations ). A pastrami sandwich at Zingerman's Deli is a 40-year tradition, but if you're hungry for a more budget-friendly option head to Frita Batidos and take a seat at one of the communal tables for Cuban-inspired street food. Hit the books at Literati, a beloved independent bookstore. A fun hotel choice is Graduate Ann Arbor with its University of Michigan-themed decor.

[See more of Ann Arbor: Things to Do | Hotels | When to Visit | Photos ]

About 140 miles northwest of Chicago, Madison is more than just a cool college town: It's also the capital of Wisconsin. No trip here is complete without visiting the beautiful, white-domed Wisconsin state Capitol building; free tours are given throughout the day. Madison's isthmus location on a narrow strip of land between two lakes means waterfront biking and hiking trails abound. Foodies will also get their fill at Fromagination, a cheese lover's paradise popular with Wisconsin cheeseheads as well as out-of-town visitors. Located across from the Capitol, this delightful cheese shop features dozens of one-of-a-kind artisanal Wisconsin varieties. If visiting Madison between April and November, head to Capitol Square on Saturday morning for the Dane County Farmers' Market, the country's largest producer-only farmers market. The 72-room, collegiate-themed Graduate Madison hotel is an easy walk to campus, dining, shopping and nightlife. Decorated in the University of Wisconsin colors of red and white, the hotel gets high marks from guests for its nostalgic decor and artwork, including collages of political buttons, a nod to the town's legacy of social activism.

[See more of Madison: Things to Do | Hotels | When to Visit | Photos ]

Those who have more time could leave the bright lights of Chicago for the serenity of Michigan's Traverse City to visit Sleeping Bear Dunes National Lakeshore and its 64 miles of pristine coastline and mountains of sand dunes. Traverse City is about 300 miles from Chicago, but you'll be rewarded with breathtaking beaches, peaceful hikes, top-notch cuisine and the added perk of what's considered the " Napa Valley of the Midwest": the 24 wineries of the Leelanau Peninsula Wine Trail. When the temperatures drop and the snow arrives, a great winter weekend getaway involves cross-country skiing in Pere Marquette State Forest or the Leelanau Trail, which runs from Traverse City to Suttons Bay. Traverse City and northern Michigan are also filled with summer lake resorts: Top options include Lake Leelanau's Fountain Point Resort, the upscale Homestead Resort and the all-inclusive White Birch Lodge in nearby Elk Rapids. With White Birch known for its water sports program, teens and tweens will love water-skiing, tubing and ending the day swapping adventures with new friends around a beach bonfire.

[See more of Traverse City: Things to Do | Hotels | Tours | When to Visit | Photos ]

Best known as the location of the Kentucky Derby, Louisville sits 300 miles south of Chicago and has a whole lot more going on than just horse racing. About 95 percent of the world's bourbon is made in Kentucky ; for a taste of the state's signature liquor, head to downtown Louisville's historic Whiskey Row. Here you'll find distilleries, unique restaurants and live music. Topping any sports lover's itinerary should be a visit to the Louisville Slugger Museum and the Muhammad Ali Center , which visitors applaud for honoring the boxer's life, faith and humanitarian service. Art lovers would enjoy staying at the 21C Museum Hotel Louisville , which houses its own contemporary art museum.

[See more of Louisville: Things to Do | Hotels | Photos ]

About 300 miles southwest of Chicago, just over the Illinois border along the Mississippi River, sits this Missouri city. St. Louis is well worth a weekend trip for its plethora of restaurants, breweries and cultural treasures. Nicknamed the Gateway City for its iconic Gateway Arch , St. Louis gives travelers the chance to take a tram ride to the top of this engineering marvel. After getting a bird's-eye view of the surrounding area, head over to the nearly 1,300-acre Forest Park , site of the 1904 World's Fair, now home to the Saint Louis Zoo and several museums. Music lovers can't miss the National Blues Museum, which sings the praises of that melancholy American music form. If you find yourself in need of more music lessons, make your way to the Scott Joplin House State Historic Site, where the king of Ragtime lived. After a busy day sightseeing, Drury Plaza Hotel St. Louis at the Arch makes a good place to rest. Guests rave about the unbeatable value of the hotel's free breakfast and happy hour with complimentary hot food and drinks.

[See more of St. Louis: Things to Do | Hotels | When to Visit | Photos ]

The Twin Cities of Minneapolis − St. Paul straddle the Mississippi River, about 450 miles northwest of Chicago, with Minneapolis as Minnesota's most populous city and St. Paul as the state capital. Minneapolis is known as a city of lakes, but visitors also like to walk along the riverfront, taking in the magnificent Mississippi. Groundbreaking pop musician Prince was born in Minneapolis; now his legacy lives on at Paisley Park, a sprawling complex in the nearby town of Chanhassen that was once the artist's studio and home. Millions more travel here to visit the largest mall in the Western hemisphere, Mall of America , located in the nearby suburb of Bloomington. As much an entertainment complex as a retail center, this mall houses the indoor amusement park Nickelodeon Universe, a highlight for kids. Guests give Minneapolis' Hewing Hotel stellar reviews for its character, charm and stunning views from the rooftop lounge.

[See more of Minneapolis − St. Paul: Things to Do | Hotels | When to Visit | Photos ]

You might also be interested in:

• The Best Weekend Getaways
• The Top Romantic Getaways in Illinois
• The Top Romantic Getaways in Wisconsin
• The Top Romantic Getaways in Michigan
• The Top Romantic Getaways in Ohio
• The Top Fall Weekend Getaways
• The Top Travel Neck Pillows
• The Top Travel Backpacks
• The Top Duffel Bags

Tags: Travel , Midwest Vacations , US Vacations

World's Best Places To Visit

• # 1 South Island, New Zealand
• # 4 Bora Bora

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23 Best Things to do in Chicago in Winter

Chicago in winter gets a bad rap, but it's a truly magical time to visit the Windy City.

Chicago in winter gets a bad rap. With frigid wind and freezing temps, locals frequently wonder why they live in a place where it hurts to breathe.

Honestly? I think they doth protest too much.

As a Chicago area resident since 2001, thirteen of those years in the Windy City itself, I can verify that the winter season in northern Illinois can be a bit testy. We’ll go stretches of days, and sometimes weeks, without sight of the sun.

We’ll get a foot of snow in a day, and then when we think winter’s gone, she’ll come back for one last hurrah. That wind can be brutal, stinging your face like an acupuncturist gone haywire.

Chicago winters are a magical time of the year. The city unfurls all its finery, with decorated storefronts, streets draped with thousands and millions of lights, ice skating, and festivals.

There’s even a real, live holiday evergreen tree culled from a local’s land that towers over Michigan Avenue.

From an authentic German market to an indoor winter wonderland, to free days at the city’s world class museums, Chicago’s a cold-weather destination that will warm your heart.

Bundle up and see why you’ll want to explore Chicago in winter.

Your Guide to Winter in Chicago

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Tips for Visiting Chicago in Winter

The winter months may be magical in Chicago, but that doesn’t mean you can simply show up like you can during the summer.

With an average temperature of 26.4 degrees and the dreaded wind chill making it feel even colder, visiting Chicago in winter requires a little more preparation, and lots and lots of layers.

Here are some top tips for visiting Chicago in winter.

Layers, layers, layers. And more layers. Did I mention layers? Cold weather is easy to handle, as long as you dress for it, and if you’re touring Chicago in winter, layers are key.

Cover everything. Wear a scarf, a hat, and gloves.

Comfy boots that you don’t mind getting dirty. Snow and ice means salt, and salt does a number on shoes. Skip suede; forget leather.

Pick footwear that you can easily clean or you don’t care about getting dirty.

Shoes with tread . Snow and ice mean slickery sidewalks and streets. They do a good job of keeping both clear, especially downtown, but you don’t want to take a chance by wearing those oh-so-cute shoes that have no tread.

If you’re going somewhere fancy, either valet or change shoes when you get to your destination.

Wear a mask. Not only will it keep you from getting the cold (or something worse) from that person next to you in line for gluhwein, masks also warm your face.

Use the Pedway. Downtown Chicago has this amazing underground tunnel system called the Pedway.

It connects several businesses, including Macy’s, the Thompson Center, multiple CTA and Metra stations, and the Chicago Cultural Center.

In the winter, the Chicago Pedway becomes its own destination, including shops and restaurants.

Know where you’re going. Nobody wants to pull up Google maps in the middle of a January gale, because that’s exactly when your phone will freeze while you’re standing there freezing. Know your route ahead of time.

Be in the know. Read Living Landmarks of Chicago before you go and you’ll have the inside scoop on all those “cool” buildings.

Want to make Chicago your home base for some Midwestern adventures? Check out these road trips from Chicago .

Things to do in Chicago in Winter

Ready to get excited about all the fun you can have in Chicago in winter? Let’s explore a few of our favorite things!

Outdoor Chicago Winter Activities

Go ice skating in downtown chicago.

Ice skating in the heart of a bustling city is a quintessential winter activity and some of the best ice skating rinks are in downtown Chicago.

The most popular is the McCormick Tribune Ice Rink . In Millennium Park, right on Michigan Avenue, you’ll be skating next to Cloud Gate and steps away from the Art Institute of Chicago with Chicago’s Cultural Mile as your backdrop.

Skating is free and you can rent skates.

There are lockers if you want a place to store your things and any purchases you’ve made at of the shopping malls in downtown Chicago .

For an alpine twist on your Chicago ice skating, head to Maggie Daley Park .

Their skating ribbon is twice as long as a regular rink, but if you need a break, there are places to exit in the middle so you can get a cup of hot chocolate.

TLTip: Both Millennium Park and Maggie Daley Park are part of Grant Park.

The Chicago Park District also has ice skating rinks around the city’s neighborhoods.

Ride the Centennial Wheel at Navy Pier

A Ferris Wheel? In winter? Have I gone mad?

Not when it’s the Centennial Wheel, one of the many attractions at Navy Pier . You’ll get an incredible view from two-hundred feet in the air over Lake Michigan in these climate-controlled cars.

Make sure to bundle up in case you have to wait in line, but once inside, you’ll be nice and toasty.

Get tickets to ride the Centennial Wheel.

Watch the Chicago Holiday Tree Lighting

The lighting of the official holiday tree of Chicago heralds the beginning of the season.

It takes place the Friday evening before Thanksgiving in Millennium Park and, like all holiday events in the park, is free to attend.

The evergreen is a real tree that’s been selected from entries submitted by residents within 100 miles of the Chicago Loop and it must be at least 55 feet tall.

Celebrate the Magnificent Mile Lights Festival

The  Magnificent Mile Lights Festival  takes place the weekend before Thanksgiving and features live concerts and special offers at Michigan Avenue shops. 

It’s definitely one of the more popular outdoor activities to enjoy Christmas in Chicago .

Pioneer Court is the epicenter of all the fun, with family-friendly and themed activities, including a holiday market.

Find your inner German at Christkindlmarket Chicago

Prost! Christkindlmarket Chicago is a long-standing winter tradition. Every November, Daley Plaza turns into an authentic German market, complete with pretzels, bratwurst, cuckoo clocks, gluhwein, and the Christkindl herself.

This market is one of the things that makes Chicago one of the best Christmas towns in the USA .

TLTip:  The Christkind is an angel that led parades during the holiday season. Traditionally robed in gold and white, she would distribute gifts to children like Santa Claus, even delivering the gifts on December 24 while the kids are still sleeping.

Want to explore more of Chicago? Save up to 50% on Chicago attractions with Go City passes .

Commune with Nature at Chicago Botanic Garden

There’s nothing like the hush of a snow-covered garden, especially when it’s Chicago Botanic Garden . With dwarf conifers and the Malott Japanese Garden, this Glencoe destination proves there’s beauty year round.

When you get a bit chilled, head inside and tour the greenhouses. Orchids and banana plants will have you feeling downright tropical.

Chicago Botanic Garden is also one of the top things to do in Chicago in Spring .

Light up at Lincoln Park Zoolights

Speaking of lights, ZooLights Chicago at Lincoln Park Zoo is another of the city’s favorite holiday traditions. The zoo is lit up with over two million lights, and strands drape every tree in the park.

Stroll through the exhibit houses and marvel at giraffes, penguins, gorillas, lions, and any of the other myriad animals that call the zoo home.

Cheer on the Chicago Bears

Sports fans can head to Soldier Field and cheer – or boo – the Chicago Bears. This outdoor stadium is located in the South Loop near the Museum Campus.

One of the most popular things to do during Chicago winters is to tailgate before the game. Parking lots open up a few hours before the game, and you can even hire Tailgater Concierge to set up your pre-game celebration.

Indoor Winter in Chicago Activities

Not all the fun is outside. Check out these great Chicago indoor attractions so you can escape that winter weather.

See Chicago from Above

Get a bird’s eye view of Chicago at one of two observatories.

360 Chicago is perched 94 stories about the Windy City in the building formerly known as Hancock. 

Not only are there commanding views of Lake Michigan and Chicago’s towering skyscrapers, including Willis Tower, you can also look down, down, down when you ride Tilt, a glass wall that tilts away from the building.

Get tickets to 360 Chicago .

Skydeck Chicago is located across downtown in Willis Tower. This 103rd-floor observation deck has its own daredevil fun: The Ledge.

These glass-paneled boxes give you a clear view all the way to the street. Get tickets to Skydeck Chicago .

Get festive at Navy Pier Light up the Lake

Nearly 500 trees decorated with 25,000 ornaments fill Navy Pier’s Festival Hall at this Chicago winter event. It’s a family-friendly way to see Christmas lights during this festive season.

Entirely inside, the festival offers several activities and the hall is filled with Christmas decorations like candy canes, Christmas trees, and lights galore.

There’s even an indoor ice skating, so you can glide with the greatest of ease while staying nice and cozy.

There are also kiddie train rides, a gift market, Merry Main Street presented by Brach’s, and a holiday beer garden.

Celebrate the Holiday Spirit with Scrooge and Co

No winter season in Chicago would be complete without experiencing A Christmas Carol.

The Goodman Theatre’s rendition of this timeless Dickens classic is a masterful production that captures the essence of the holiday spirit.

With its top-notch acting, intricate set designs, and a story that resonates across generations, it’s more than a play—it’s a Chicago institution.

Get tickets to A Christmas Carol

Visit Chicago’s World Class Museums in Winter

Winter is an ideal time to visit Chicago’s world-class museums. Not only do they offer an escape from the chilly weather, they also entertain and educate.

Illinois residents are in luck because winter is the time for many Chicago museum free days.

These free admission days vary by museum and usually begin in January. There’s a reason these are some of Chicago’s most popular tourist attractions.

Here’s a quick run-down on what I call the Big Five Chicago Museums:

Adler Planetarium

Adler Planetarium museum is the oldest planetarium in the U.S. and features three full-size theaters and several interactive exhibits.

It also hosts an extensive collection of historical artifacts that reach back to medieval Europe and the Middle East.

Art Institute of Chicago

The famed Art Institute of Chicago houses over a quarter of a million works of art that represent more than 5,000 years of human expression.

There are galleries devoted to art from countries all over the world as well as to different mediums.

Field Museum of Natural History

The Chicago Field Museum features millions of specimens that showcase art, archaeology, science, and history.

Some of the most impressive exhibits are the Grainger Hall of Gems and the largest T. rex skeleton ever excavated.

Museum of Science and Industry

The Museum of Science and Industry should make anyone’s short list of things to do in Chicago during winter. With over 35,000 artifacts over 14 acres, the museum is a destination worth visiting again and again.

During the holidays, the museum is particularly festive. Each year since 1942, the  Museum of Science and Industry  celebrates the holidays with  Christmas Around The World and the Holidays of Light . 

Over fifty trees represent Chicago’s diverse ethnic communities, decorated by volunteers who want to share their cultural traditions.

Shedd Aquarium

The Shedd Aquarium is one of the most popular museums in Chicago. Visitors can see aquatic and amphibian life from all over the world.

There are 80 different habitats represented. There are also live shows featuring dolphins, penguins, and even Beluga whales.

Chicago has a thriving theater scene, and one sure way to be entertained during those cold winter months is to take in a show.

From Broadway in Chicago to the renowned The Chicago Theatre and Steppenwolf Theatres, to black box storefronts that dot the city’s neighborhoods, there’s a type of performance for every taste.

Check out this Chicago events calendar to find performances during your Chicago winter vacation.

Learn about Chicago’s Past

Chicago’s past is CRAZY. I should know – I wrote a book about it.

One of the stories in Living Landmarks of Chicago is about the Chicago History Museum. Organized as the Chicago Historical Society in 1856, today the organization’s collections include approximately 22 million specimens.

One of the Chicago History Museum’s most beloved exhibits is Imagining Chicago: The Dioramas . They were unveiled in 1932 and they’re still around.

Eat in an Igloo

City Winery on the Chicago Riverwalk started the igloo dining craze in Chicago, and since that first climate-controlled experience opened, several more restaurants and bars have joined in.

You can even dine outside on a rooftop. In Chicago. In winter. LondonHouse Chicago and I|O Godfrey, among others, will be offering the seasonal dining option.

Get your Garden Fix at Garfield Park Conservatory

When you need a spot of green, head west to Garfield Park Conservatory . This wonderful place is open year-round and is considered one of the most beautiful botanical conservatories in the country.

Admission is free, and donations are encouraged.

Vroom Vroom at the Chicago Auto Show

The largest auto show in North America takes place every February at McCormick Place. The Chicago Auto Show has been celebrating the automobile since 1901.

For ten days, you can check out the newest vehicles. More than just a static showroom, there are also indoor test tracks so you can how those cars move.

Related: find hotels near McCormick Place

I hope it’s obvious that there are tons of things to do in Chicago in the winter. Will you be planning a visit during this time of year?

More articles to help you explore Chicago:

• You’ll never be bored with these best  things to do in Chicago
• Chicago on a budget : how to save money in the Windy City
• Road trips from Chicago , for when you want to get out of town
• Tiptoe through the tulips during  Chicago in spring
• Chicago in summer  is delightful
• Discover why the  Field Museum  is the beloved institution that almost wasn’t
• How one man’s vision became the  Museum of Science and Industry

• Activities for Kids

Winter Escapes a Road Trip Away from Chicago

Get out of the house this winter and discover three amazing winter getaway destinations

Staycations are great , but being away is sometimes just what we need. Kids dig hotel stays for the chance to sprint down long hallways and jump like monkeys on the bed. Parents love vacation for the squad-bonding opportunity, replacing the same ole for a new scene and having someone else make the bed for a change. Find great winter destinations that allow for time in the great outdoors and lots of memory-making.

The American Club - Kohler, WI

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Buckle the kids in for a drive 145 miles north of Chicago to the city best known as home to the Kohler company, recognized for its high-quality faucets and bathroom products. But you don’t need to come for the potty talk, folks. Sit back and enjoy all this town has to offer.

For a romantic couples getaway or girlfriends' retreat to the spa, the five-star The American Club and the contemporary The Carriage House guest rooms are your go-to spots. The adults-only atmosphere provides a nice break from any school-year chaos and you and your travel mates will be treated to complimentary yoga, indoor cycling, a Himalayan salt stone lamp, Peloton stationary bikes are provided in select suites and a Wellness Concierge helps to maximize your time and experience.

Families will be more comfortable in the private cabins with gorgeous views, or at the Inn on Woodlake , which features boutique-style guest rooms as well as multi-bedroom suites. They even have a limited number of dog-friendly rooms, so the family pet can tag along.

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Kids stay happily entertained with oodles of family activities that include zombie dodgeball, TopGolf swing simulator, indoor tennis lessons, ice skating, hiking, snowshoeing, sledding, and fat tire biking. If you're in need of time in the kid-free zone, register for the Saturday evening Kidz Dinner and Movie. Kids will enjoy a night of food, movies, and games, while you dine, explore the onsite spa or just catch some much-needed zzz’s. As a bonus, when receiving services at the spa, you can utilize the childcare for at Kids Core at the Sports Core Health & Racquet Club just minutes away.

Add a little culture to your itinerary and visit the John Michael Kohler Arts Center located just five minutes away. With the Art Center's help, stay outside, by taking The Sheboygan Project Walking Tour , which brings the street art movement to Sheboygan. The urban landscape and available wall space is the canvas for works that reflect the city's people and culture.

French Lick Resort - French Lick, IN

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Peace. Quiet. Relaxation. You might have forgotten the meaning of the words, but you’ll quickly recall them at the French Lick Resort in this quiet town snuggled aside a sulfur spring in the southern Indiana woodlands.

This sprawling getaway spot is known for KidsFest , an indoor-outdoor area dedicated to little travelers. Activities include bike rentals, bowling, an arcade, arts and crafts projects, cooking classes, horseback riding, and video games. There’s also an indoor pool, footgolf, horse-drawn carriage rides, and several family-friendly restaurants onsite.

If you find yourself with kid-free time and can resist the urge to nap, bathe in the rejuvenating mineral springs, leave your stress at the spa, shop the Promenade or play the odds at the casino.

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You can easily spend days without leaving the hotel, but it’s worth exploring the area. Nearby Hoosier National Forest has miles of hiking, biking, and horseback riding trails;  Patoka Lake  is a pretty place for anglers-in-training to cast a rod; and  Morengo Cave is full of gems that you can mine for and take home.

For western-style fun, check out a working cattle ranch and go ziplining, ATV-riding, see a drive-thru lights show, and experience a Drive-Thru Safari Park to see more than 40 species of animals at Wilstem Ranch . Even if the weather isn’t cooperating, you can put on your swimsuit and dive into 40,000 square feet of slides, drops, lazy rivers, and wave pools at Big Splash Adventure Indoor Water Park .

Lake Lawn Resort - Delavan, WI

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This getaway spot has a history that is 130 years rich and is situated in tranquil woods 90 miles northwest of Chicago in Delavan, Wisconsin. Evidence of the land’s Native American beginnings can be seen in the property’s 40 remaining effigy mounds, the largest collection in southern Wisconsin. It was also once the longtime headquarters of the largest traveling circus of its day, Mabie Brothers US Olympic Circus.

A great time to plan a Lake Lawn Resort adventure is in the winter for all of their winter fun activities. Take the kids sledding down the Rudy Lange Sledding Hill or go explore a historic site or museum and learn something new.

No matter when you make your way north, there are plenty of activities to keep this vacation from heading south. With four restaurants (ranging from fine dining to classic bar and grill), an arcade to display your Dance Dance Revolution prowess, and a spa to massage any twerking injuries, you never need to leave. Go for a swim in the heated indoor pool, make a craft in the Kids Zone, or go cross-country skiing, ice skating, or snowshoeing.

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You could easily hole the family up in the resort and never leave, but The Dancing Horses Theatre located nearby is worth venturing away from the cozy fire. Trainers treat guests to a parade of equestrian showmanship, followed by the mischievous antics of an exotic bird show that will leave the kids in a fit of giggles.

Nearby Lake Geneva hosts the U.S. National Snow Sculpting Competition during the village’s annual Winterfest , Feb. 1-5. Festival-goers are treated to the intrigue of snow sculpting as well as music, helicopter rides, laser tag, s'mores, bonfires, and dog sled races.

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19 Awesome Road Trips from Chicago (with Timings)

Keeping your introduction to road trips from Chicago short and simple, let’s take a look at the summer, winter and weekend favourites!

The city of Chicago is awesome and all, but it’s also a great starting point for some great Chicago road trips. The city’s prime location acts as a portal to the Midwest – from historical cities to sprawling state parks and urban-stress-relieving beer. 

Best Chicago Road Trips in Summer

If you’re looking for one of the longest Chicago road trips, how about driving from Chicago to New Orleans ? If you’re thinking a little shorter, then read on…

Distance: as far as you can go

No American road trip is complete without covering some part of classic Road 66 – of which, lucky for us, kicks off in Chicago!

Snap a selfie at the official sign between East Adams and South Michigan Avenue then check-off stops such as the Gemini Giant, the Pontiac murals, Lincoln Presidential Library and more. If you can spare a month, make it all the way down to the Pacific Ocean.

2. Illinois’ Great River Road

Distance: 3.5-hour drive

In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.

Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes. 

3. Lake Michigan to South Haven

Distance: 2.5-hour drive

Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.

There are plenty of berry farms along the way so you can stain your hands with blueberries; or maybe you prefer to climb up a lighthouse?

To take your road trip even further, bring a bike! Cruise along the water front; take a dip or two. 

Do you have a favourite road trip quote? Click for the best long drive quotes to inspir e your next adventure!

4. Shawnee National Forest

Distance: 6-hour drive

One of the longest Chicago road trips on the list, it’s more than worth it to visit Shawnee National Forest. In fact, plan to camp amidst the spectacular range of landscapes for one of the best driving trips from Chicago!

Local favourites include the Garden of the Gods – you’ll find super special rock formations like Anvil Rock. Little Grand Canyon and Bell Smith Springs feature moderate hikes; Inspiration Point offers panoramic views over the prairie, Mississippi River and the forest.

Not convinced? Shawnee Hills Wine Trail is a brilliant drive that links up vineyards and wineries in the area – a great stop on a road trip from Chicago.

How about driving from Chicago to Atlanta? Here’s my guide to the best stops on a Chicago to Atlanta road trip , just for you.

Best Chicago road trips in Winter

If you want the best road trips from Chicago when it’s colder and darker, then these are the best ones for you.

5. Grand Rapids

Distance: 3-hour drive

After just long enough of a drive, pull into Grand Rapids for a nice sweep of activities. The Beer City Ale Trail will keep you road-tripping on foot (or car, if you have a Designated Driver); or wander through Downtown Market for food adventures instead.

Warmed by booze, drop by the 158-acre Frederik Meijer Gardens & Sculpture Park where their installations are bright pops of colour against an all-white backdrop. 

6. Muskegon

Speaking of unusual winter activities, I’ve heard so much about Muskegon Winter Sports Complex. Just an hour from Grand Rapids, it’s a great next stop on your Chicago road trip.

Their Olympian-designed ice-luge course is perfect for beginners, spanning 850 feet of forested speed racing. Muskegon is also home to USS Silversides Submarine Museum if you’re into marine vehicles, and there’s a great pier and lighthouse too.

7. Indianapolis

When temperatures are cold, cold, cold – you might opt for staying indoors. The city of Indianapolis is one of the best road trips from Chicago during winter because of its incredible indoor entertainment: museums.

From the Indianapolis Museum of Art to the Indianapolis Children’s Museum to quirky Indiana Medical History Museum, you can escape the cold all day!

Of course, drop by famous City Market for great eats and then maybe go on a catacombs tour underground too. This makes for one of the best road trips from Chicago.

8. Boyne Mountain Resort

Distance: 5-hour drive

Michigan winters are best captured with the ski resort of Boyne. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades.

While the forested grounds offer romantic snow-covered views, don’t miss out on the epic zip lines that take you through the trees and slopes. 

If you like your road trips from Chicago with a bit of snow and ski thrown in, then this is a great option for you.

Your ESTA for the USA

Before you go to the USA make sure you have your ESTA organised. You can find help with this on this link: https://www.application-esta.co.uk/ESTA-guide . It doesn’t take long and organising it beforehand will make things go that bit smoother at the airport.

9. Apostle Islands

Distance: 7-hour drive

Does driving over ice count as going off-road?

It’s an unforgettable journey to Apostle Islands National Lakeshore as winter ice freezes thickly to transform water into road, ending with stunning ice caves!

Make sure to visit the only inhabited Madeline Island as well for a cool wind sled experience and hot tub stay. 

Day Road Trips from Chicago

10. lake geneva.

Distance: 1.5-hour drive

Chicago’s number one when it comes to day trips, Lake Geneva is one of the best lake town’s in the US.

Downtown boasts all the food and drinks you need for the inevitable food baby; you might even land a booze cruise.

Hot air balloon rides, Lake Shore Path, ziplines and even ski slopes make it a year-round place to visit. It’s a multi-visit destination for sure!

11. Harbor Country

Distance: 1-hour drive

Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.

It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world. 

12. Starved Rock State Park

Distance: 2-hour drive

Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.

It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views. 

13. Saugatuck 

Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!

Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.

14. Elkhart Lake

I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.

You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!

Want a charming hideaway? This is it.

Road Trips 4 hours from Chicago

Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.

15. Ann Arbor

If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.

Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings! 

16. Door Country

Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!

You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.

You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19 th century.

For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round. 

18. Richland County

To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.

The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?

You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way. 

19. Huron-Manistee National Forest

Michigan really surprises us again and again!

Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers. 

Road trips from Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead. 

Related Posts:

• 7 Ways to Make the Most of Your Road Trip Budget
• Planning a Road Trip in the USA: 13 Best Routes!
• 57 Coolest Things to Do in Chicago for 2023
• Christmas Things to Do in Chicago in Winter: 21+…
• 14 Awesome Stops on a Chicago to New Orleans Road Trip
• 11 Unique Stops on the Drive from Chicago to Atlanta

Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

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The Best Winter Getaways Near Chicago

The summer months have come to a close, and for many of us, 2020 was a year without too much travel. Combine that with the winter weather, and you may find that you are eager for a change of scenery and a little adventure! The good news is that Illinois offers plenty of opportunities for safe, local getaways to satisfy your travel bug. From wineries and spas to ice climbing and remote cabins, here are six unique places for you to explore this winter. Please be sure to check all websites for the latest updates on COVID-19 restrictions and safety practices.

1. Starved Rock Lodge

Nestled deep within Starved Rock State Park , this winter getaway offers a variety of accommodations and activities so that you can tailor your trip to your preferences. If you stay in the main lodge, you can choose to vacation either in a historic room built by the Civilian Conservation Corps in the 1930s or in a newer and more spacious hotel room. If you prefer a more rustic and remote experience, cozy and historic cabin accommodations are also available.

Voted the number one attraction in the state of Illinois, the Starved Rock State Park also offers a multitude of activities, including scenic hikes, ice fishing, and even ice climbing (when conditions permit). If you’d rather explore the area on wheels, you can reserve a spot on the resort’s trolley tour. 

The lodge is also situated near many area attractions like August Hill Winery in Utica, Tangled Roots Brewery in Ottawa, Hegeler Carus Mansion in LaSalle, Reddick Mansion in Ottawa, LaSalle County Historical Museum in Utica, Weber House and Garden in Streator, and more. Don’t forget that Starved Rock Lodge is also your one-stop shop for holiday gift shopping . 

2. Galena Cellars Vineyard and Winery in Galena

If you’re planning a romantic getaway, check out their one-bedroom suite located above the tasting room with a view of the vineyard. You’ll also have access to an array of amenities like a fully equipped kitchen, a fireplace, a whirlpool tub, and much more.  

If you’re looking for a little more room, you can reserve the vineyard’s two-bedroom vineyard farmhouse located within walking distance of the vineyard and tasting room. Amenities include a large outside yard and deck, a fully-equipped kitchen, a flat-screen TV and Dish network, and much more. Please note that a two-night minimum stay is required. Get ready to relax in style because all lodging reservations come with a complimentary glass of wine or wine flight per guest!

3. Blue Sky Vineyards in Makanda

Missing international travel? Blue Sky Vineyards offers a taste of Italy in Southern Illinois. The Blue Sky Vineyard tasting room and accommodations are designed to emulate the classical Tuscan style, with stucco walls, carved doors, hand-hewn beams, and 200-year-old Portuguese tiles. Choose between the elegant and cozy Blue Sky Suite and the opulent Tuscany Romance Suite with a living room, dining room, and balcony. During your stay, you’re also welcome to explore the breathtaking views of the Shawnee National Forest in which the vineyard is located. 

4. The Stablehouse in Alto Pass

If you’re in need of a break from the big city, look no further than the stable house, a charmingly rustic, 75-acre farm with a comfortable guest house and plenty of room for all of your four-legged friends - that’s right, this is a vacation for the whole family, pets included! The guest house includes a full kitchen and sleeps up to six people. It’s perfect for hunters, hikers, horse owners, and anyone wanting to experience the simple and rejuvenating joy of country living.

Located along the Shawnee Hills Wine Trail, this vacation home also offers plenty to do nearby. Enjoy easy access to local wineries as well as beautiful natural areas like the Shawnee National Forest, Giant City State Park, Cypress Creek National Wildlife Refuge, Cache River Wetland Center, Fort Massac State Park, and much more.

5. Kohler Waters Spa - Burr Ridge 

The Kohler Waters Spa in Burr Ridge offers a range of amenities and services, including massage therapy, hydrotherapy treatments, facials, bathing, body treatments, nail treatments, make-up and waxing, a steam room, a sauna, and other signature treatments similar to those offered at the spa’s Forbes five-star flagship in Wisconsin. While there isn’t an option for an overnight stay, you’ll leave the spa feeling refreshed.

6. Big Sky Cabins in Alto Pass

Do you miss seeing the stars in a clear night sky? Rated number 1 on the Southern Illinois Wine Trail, Big Sky Cabins offers a remote and private getaway for anyone wanting to experience the splendor of the Shawnee National Forest and the tastes of the Shawnee Hills Wine Trail. Lodging options include the Alto Wine Trail Loft, the Cabin on the Creek, and the Wine Country Farmhouse. Accommodations are just 12 minutes away from the vineyards. 

7. Your Home in Chicago's Northwest Suburbs

Getting away from home can put into contrast just how different Airbnb's, hotels, cabins, and other destinations can be from your home. But it doesn't have to be that way! Renovating your home in Chicago's northwest suburbs could be the perfect thing to do to create a luxurious oasis this winter.

Discover what's involved in planning a home renovation project to see if a home remodel could be right for you, and next time, your home could be even better than a winter getaway! Download the eBook " The Ultimate Step-by-Step Home Renovation Transformation Guide. "

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The best winter getaways near chicago.

In the Chicago area, it isn’t uncommon to feel confined indoors during the long, chilly winters. While it’s more traditional to travel in summer, you may be surprised to discover that some of these getaways are actually more picturesque in winter. And if you’ve hired contractors to transform your home over the holidays, what better way to escape the noise than to get out of the house and find cheer and refreshment in nature’s abundant tranquility!

Family-Style Holiday Cabins in Wisconsin Dells

If your ideal Christmas involves cocooning yourself inside a rustic log cabin nestled in a pristine blanket of snow while sipping cocoa by the fire with family and friends, you can drive just over three hours to the Wisconsin Dells. Everyone knows Sand County as a popular summer resort scene, but in winter, the Dells transform into a quaint and charming scene worthy of a Thomas Kinkade painting. You can rent homes, cottages, condos, or cabins of all sizes. Did we mention that the Dells are also a famous destination for delicious dining ? You can reserve your family-style holiday cabin getaway here .

Skiing and Snowboarding at Chestnut Mountain in Galena

While a mere change of scenery works wonders to beat the winter blues, some of us also seek more active ways to enjoy the holidays. Galena, IL’s Chestnut Mountain resort is under three hours away, and it’s got some of the best skiing and snowboarding slopes in the area. If you’re a professional, you’ll love the 3,500 feet of beautiful slopes, and if you’re an amateur, the variety of group, private, and semi-private lessons have got you covered . At the day’s end, you can soak in a jacuzzi or warm up in a sauna at the resort.

Relaxing at Grand Traverse Resort and Spa

Just under five hours away, the Grand Traverse Resort and Spa is a bit of a trek, but for a long weekend away, it’s worth it. Traverse City has a little bit of everything--it’s famous for its vineyards like Bower’s Harbor , its craft beer scene with destinations like Shorts Brew Pub , and its fine dining . On the resort itself, you can enjoy activities like winter golf, indoor water playgrounds and pools, spa treatments, shopping, ice skating, snowshoeing, and cross country skiing. Staying at the resort also gives you easy access to a local theater, sleigh rides, downhill skiing and tubing, snowmobile rentals, and more!

Romantic Getaway at the Inn at Bay Harbor

If you’re up for driving just North of Traverse City, you’ll find yourself at the stately Inn at Bay Harbor near Petoskey, MI. This stately inn overlooks Lake Michigan, whose shoreline is breathtakingly beautiful in winter. Take advantage of the full-service spa treatments or salon after exploring local boutique shopping. The Inn even offers a Romance Package , starting at just $190 a night, that’s perfect for anniversaries or just taking time to reconnect with your special someone away from the stresses of everyday life. 

Because Chicago is a destination city, it’s easy to habituate yourself to day trips within city limits. But part of what makes Chicago such a great place to live is that it’s centrally located near other destination cities and vacation resorts. So this winter, make the most of living in Chicago by exploring nearby gems that give you a change of scenery, a release for your cabin fever, and a chance to slow down and enjoy the season.

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Will Hike For Beer: New Book Pairs Local Trails With Breweries To Get Chicagoans Outside

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LINCOLN SQUARE — Urban hiking enthusiasts and married couple Jessica Sedgwick and Dan Ochwat rarely take a local hike without heading to a local brewery afterward. That’s because these nature-loving craft beer connoisseurs believe nothing beats a cold pint after a day on the trail. 

Inspired by a shared love of Chicago’s craft beer scene and their routine hiking adventures in city parks, the Cook County Forest Preserves and beyond, the Lincoln Square-based couple has compiled what they consider the best brewery and hiking trail pairings in and around Chicago into a new book.

“ Beer Hiking Chicago and Beyond: The Tastiest Way to Discover the Windy City ,” which goes on sale Tuesday, shares 30 family-friendly hikes in the city and surrounding suburbs and a few day trips in Central Illinois, Wisconsin, Indiana and Michigan. Each hike is paired with a nearby brewery or tasting room within a 10-minute drive from the trailhead. 

Sedgwick and Ochwat will discuss their book during a launch party 7 p.m. Tuesday at The Book Cellar, 4736 N. Lincoln Ave., with free beer tastings provided by Glunz Beers .

“This book doubles down on the history and personality of Chicago and its surrounding communities, offering a look into how each hiking trail and brewery plays into that thread,” Ochwat said. “We hope the book helps get [readers] out of their neighborhood and into other communities across the city and suburbs — to go see, enjoy and explore.”

The guidebook-style paperback leads readers through a mix of stunning landscapes, striking cityscapes and natural hidden gems. The adventures range from 1 to 5 hours and include descriptions of the trail and natural area — from details on access, difficulty level and duration to historical and environmental points of interest along the route.

The book suggests post-hike stops nearby where local craft beer awaits, plus a recommended beverage, including a short description of notes on its appearance, aroma and flavor. 

“Beer Hiking Chicago and Beyond” is part of  Helvetiq’s “Beer Hiking” series , which features other regions around the country like Southern California and New York.

In addition to highlighting hikes that people might not know about in Chicago, Sedgwick and Ochwat said the book serves as a love letter to Chicago communities, their history and what makes them unique.

“History and art are big themes to the book,” Sedgwick said. “Especially within the city hike descriptions, we try to call out really cool public art and sculptures that people should stop and take a look at, as well as some of the hidden history and stories behind the park that visitors may overlook.”

Sedgwick and Ochwat drew on countless hours spent hiking trails and sipping beers in taprooms to finetune their top pairings, nine of which are in city limits, 16 in the suburbs and five a daytrip’s length away.

With over 300 breweries in Illinois, 70,000 acres of natural area across the Forest Preserves of Cook County and hundreds of natural areas beyond city limits, the choices were seemingly endless, the couple said. 

“As we say in the book, Jessica’s good at getting us from point A to point B, while I’m better at going from pint 1 to pint 2,” Ochwat said. “But, together, and with our son in tow, we enjoyed a family experience with many of these hikes. And as for the breweries, our son could write his own book on which has the best french fries and Wi-Fi connection.“

The book prioritizes lesser-known green spaces around Chicago, particularly natural areas transformed from former industrial sites or city parks into beautiful hiking trails and community spaces.

Sample pairings include Palmisano Park in Bridgeport paired with Duneyrr Fermenta , McKinley Park Natural Area paired with Marz Community Brewing and West Ridge Nature Park on the northwestern edge of Rosehill Cemetery paired with Half Acre Brewing . Other featured city neighborhoods include North Park, Schiller Woods, Logan Square, Washington Park and more.

The co-authors and Lincoln Square residents hope their book inspires more people, families and friend groups to get out and search for urban nature beyond their own backyards, something Sedgwick said all Chicagoans will benefit from doing.

“I want people to be able to see that you can find hikes, forest walks and nature outings in our city — it just takes some exploring,” she said. 

Starting Tuesday, the book will be available for purchase in select local bookstores and online .

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The best snowboarding and skiing resorts near Chicago

Bunny hills, steep slopes and breathtaking vistas—there's a lot to love about the best ski resorts near Chicago.

As fall turns to winter, area snowboarding and skiing spots are getting ready to take advantage of plunging temperatures. Plenty of places make their own snow, so even if nature hasn’t provided any, those looking for the best things to do outside this winter should plan on making a day trip to hit the slopes. Lessons for all skill levels and ages are available if you don’t have any experience or are rusty, and many destinations in neighboring states provide excellent options for weekend getaways with spas, restaurants and luxurious hotel rooms. So get  a taste of cold weather adventure at the best destinations for skiing and snowboarding near Chicago.

Skiing and snowboarding at these slopes is contingent upon weather conditions. Always call ahead or check resort websites.

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The best ski and snowboard slopes near Chicago

Alpine Valley Resort

W2501 County Road, Elkhorn, WI, 800-227-9395

Driving time from Chicago: about two hours

The gist: Winter sports enthusiasts will find plenty of variety at this southern Wisconsin ski resort, which features 20 ski runs, a vertical drop of 388 feet and three terrain parks.

Season dates: Weather permitting. Ticket to ride: Full day w eekday tickets $76 (beginner hill $57), weekends $90 (beginner hill $67); equipment rentals are $47 for a half-day and $57 for a full-day plus $15 for a helmet.

Bittersweet Resort

600 River Rd, Otsego, MI, 269-694-2820 Driving time from Chicago: about 2.5 hours

The gist: Boasting 20 runs, six chairlifts, three wonder carpets and two rope tows, Bittersweet caters to skiers and snowboarders of all ages and abilities. A separate beginner area features three chairlifts and a terrain park. Those looking for a challenge can hit the advanced terrain park, where the features change regularly.

Season dates: Weather permitting.

Ticket to ride: Weekday tickets $54 (beginner hill $44); Saturday and holiday tickets $72 (beginner hill $62), Sunday tickets $70 (beginner hill $60); reduced rates available in the evenings; equipment rentals $15–$42.

Cascade Mountain

W10441 Cascade Mountain Rd, Portage, WI, 608-742-5588

Driving time from Chicago: about three hours

The gist: Kids ages 12 and under ski for free at this Wisconsin resort as long as they're accompanied by an adult—and if you're looking for more family fun, the 900-foot-long snow tubing chute doesn't disappoint.

Season dates:  Opens November 25. Ticket to ride: $95; kids under 12 ski free with adult; equipment rentals $39–$119.

Chesnut Mountain Resort

8700 W Chestnut Rd, Galena, 800-397-1320 Driving time from Chicago: about three-hours

The gist: This resort’s 100-room lodge is situated high on the bluff of Chestnut Mountain, offering breathtaking views of the Mississippi River. Its 475-foot vertical drop runs 3,500 feet through 19 slopes ranging from beginner to black diamond. A conveyor lift, two quad chairs and four triple chairs zip you to the top of the mountain nearly as fast as you go down.

Season dates:  Weather permitting.

Boyne Mountain Resort

1 Boyne Mountain Rd, Boyne Falls, MI, 855-688-7024

Driving time from Chicago: about 5.5 hours

The gist: Arguably the Midwest’s premier ski destination, this northern Michigan resort is well worth making the long drive from Chicago. There are more than 60 runs—suitable for all levels of skiers—plus 11 lifts and seven terrain parks spread across 400 acres. You can also go snow tubing, ice skating, snowshoeing, horseback riding and more, so there’s no shortage of excitement.

Season dates: December-March.

Ticket to ride: Starts at $59, evening tickets start at $35.

Granite Peak

227200 Snowbird Ave, Wausau, WI, 715-845-2846

Driving time from Chicago: about four hours

The gist: This legendary Wisconsin resort dates back to 1937 and is one of the oldest in the country. Located within Rib Mountain State Park, it spans more than 200 acres and sports 58 trails, four terrain parks and seven lifts. Granite Peak is also the third tallest ski area in the Midwest, with a 700-foot vertical drop.

Season dates: November 22-April 7.

Ticket to ride: Nov 22-Dec 25, Fri-Sun $85; Dec 26-Apr 7 $109.

Crystal Mountain

12500 Crystal Mountain Dr, Thompsonville, MI, 855-995-5146 Driving time from Chicago: about five hours

The gist : This northern Michigan destination has it all: 59 downhill slopes for skiing and snowboarding, six chairlifts, two carpet tows, three terrain parks, seven wooded glade areas and a learning area. NASTAR racing is offered Thursday through Sunday and private and group lessons are available daily. Accommodations include luxury suites, hotel rooms, condos and resort homes.

Season dates: November 24 to April 1. Ticket to ride: Day passes start at $34; full equipment rentals start at $55.

Devil's Head Resort

S6330 Bluff Rd, Merrimac, WI, 608-493-2204 Driving time from Chicago: about three hours The gist: This South Central Wisconsin ski resort located in the Baraboo Bluffs contains one of the highest mountains in Wisconsin, with a 500-foot vertical rise. At 300 acres, it's also the third-largest resort of its kind in the Midwest. Season dates: Weather permitting.

Eagle Ridge Resort & Spa

444 Eagle Ridge Drive, Galena, 815-777-5000

Driving time from Chicago: about 2.5 hours

The gist : This resort offers complimentary transportation to the nearby Chestnut Mountain for skiing, though if you want to have some winter fun onsite you can take advantage of the Nordic Center, which offers sledding, ice skating and snowshoeing. Warm up around a bonfire or with a relaxing treatment at the 12,000-square-foot Stonedrift Spa.

Ticket to ride: Equipment rentals $10 for sleds, $15 for skates, $30 for snowshoes.

Four Lakes Alpine Snowsports

5750 Lakeside Dr, Lisle, 630-964-2550 Driving time from Chicago: about one hour The gist: With an "anyone can do it" attitude, beginners can learn to navigate the slopes in no time. These hills in the western ’burbs consist of two bunny slopes, a terrain park, an intermediate trail and an advanced trail. Season dates:  Weather permitting. Ticket to ride : Daily slope tickets $26-$34; equipment rentals $23 for skis, $33 for boards, $10 for helmets.

The Mountain Top at Grand Geneva Resort & Spa

7036 Grand Geneva Way, Lake Geneva, WI, 262-248-8811

Driving time from Chicago: about 1.5 hours The gist: The beginner- and family-friendly resort offers 20 runs, a 211-foot vertical, a six-acre terrain park, three chairlifts, two carpet lifts, and skiing and snowboarding lessons. You can also enjoy cross-country skiing, snowshoeing, ice skating, and sledding. Warm up by the fireplace at the mountaintop lodge while watching other skiers rush past.

Season dates: Opens December 16.

Ticket to ride:  Mon-Thu $65, Fri-Sun and holidays $70; rentals $10 for helmets, $45 for skis or snowboards.

Sundown Mountain Resort

16991 Asbury Rd, Dubuque, IA, 563-556-6676 Driving time from Chicago: about 3.5 hours The gist: This beautiful mountain, which overlooks 100 square miles of countryside, takes you down through a century-old cedar forest reminiscent of Colorado or Wyoming. With 21 trails, two terrain parks, a kids park, and ski and snowboarding lessons, you’ll find something fun for any age or skill level. Season dates: Weather permitting.

Swiss Valley Ski & Snowboard Area

13421 Mann St, Jones, MI, 269-244-5635 Driving time from Chicago: about two hours

The gist: This southwestern Michigan mainstay (it’s been in business for more than 50 years) features 12 slopes, two terrain parks, a 225-foot vertical drop and a fireside lounge. There's also a racing program for adults and kids, a renovated cafe, extra equipment rentals and improved snowmaking. The ski and snowboarding schools offer lessons for all abilities and there’s a full service ski & board shop to get you outfitted with everything you need.

Season dates:  Weather permitting. Ticket to ride: Weekday tickets $45, Saturday and holidays $55, Sunday and holidays $45; equipment rental $30.

Caberfae Peaks

1 Caberfae Ln, Cadillac, MI, 231-862-3000

Driving time from Chicago: about 4.5 hours

The gist: Located in northern Michigan’s snowbelt, Caberfae Peaks boasts 27 runs and three peaks, with a 485-foot drop. Once you’re done on the slopes, head to the Mackenzie Lodge and warm up by the fire or in the heated pool and hot tub.

Season dates: November 24-March 9.

Ticket to ride: Mon-Tue $44, Wed-Fri $49, Sat $79, Sun $64.

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