Things to Do in Chicago in the Winter

If there’s one city that’s mastered being able to handle copious amounts of snow while providing endless opportunities for fun, it’s Chicago.

We put together a list of our favorite things to do in Chicago in winter so you can plan the perfect itinerary, from seasonal festivals to can’t-miss attractions and everything in between.

Many of these great activities are included on the Go Chicago® Card.

Choose as you go from dozens of top Chicago attractions and save up to 55% off combined admission vs paying at the gate. Or, build your own pass and save up to 20% off.

See all available passes, attractions & prices – Learn more.

Take a Bus Tour of the City

48-Hour Hop-On Hop-Off Bus Tour

Explore Chicago at your own pace and keep warm inside a hop-on hop-off tour bus between popular attraction stops and destinations.

You’ll get to see Chicago from a bird’s eye view while taking in the sites and getting to know Chicago’s history on this narrated tour.

Go Ice Skating

Millennium Park

A photo posted by @lizlizzlizzz on

When: November 13-March 6, 2016

For skating with a view of the Chicago skyline, head to the McCormick Tribune Ice Rink at Millennium Park.

The rink, which is free and open to the public, draws more than 100,000 skaters each year. Skate rental is available for around $10.

Check online for hours and more information.

Maggie Daley Park

Go Ice Skating on the Ribbon at Maggie Daley Park in Chicago

Photo credit: Maggie Daley Park’s Official Facebook Page

When: November 14-March 15, 2016

The Maggie Daley Park Skating Ribbon rink features a skating path that weaves through Maggie Daley Park and features views of the city skyline to make for a unique ice skating experience.

Check online for more information.

Lincoln Park Zoo

Go Ice Skating this Winter at Chicago's Lincoln Park Zoo

Photo credit: Lincoln Park Zoo’s Official Facebook Page

When: November 27-February 28, 2016

Turn your trip to the zoo into a day of festive winter fun at the Lincoln Park Zoo Ice Rink.

Bring your own skates or rent a pair from the Main Farmhouse where you can warm up after gliding around on the ice with special refreshments.

Check online about admission and for more information.

Go Shopping

Go shopping in Chicago

The Magnificent Mile, which runs along Michigan Avenue, is Chicago’s most diverse shopping destination with everything from upscale boutiques to outlet stores. You’ll find big mall names like Nordstrom, Tiffany, Gap, Ralph Lauren, and more, including indoor shopping complexes at Water Tower Place and 900 North Michigan Shops.

Traveling with kids? Consider checking out American Girl Place, which is as much a tourist destination as it is a shopping destination. Located right in Water Tower Place on North Michigan Avenue, it’s a fun place to bring the kids shop, dine, or partake in afternoon tea.

Head to the Chicago Loop for more shopping, including the famous Macy’s on State Street, recognized as a National Historic Landmark, where Go Chicago Card holders get an exclusive savings of 15% off their purchase. Plan to eat lunch or dinner at The Walnut Room in Macy’s, the first restaurant in a department store.

Restaurant Week

Check out Restaurant Week in Chicago this 2016

Image credit: Choose Chicago

When: January 22-February 4, 2016

Get ready for two weeks of Chicago’s best dining experiences at participating establishments throughout the city. You’ll get a taste of Chicago’s booming culinary scene.

Check online for a list of participating restaurants and more information.

Go to a Museum

Visitors can view 23 human mummies and sarcophagi in the tomb's burial chamber

Image credit: The Field Museum

Whether you’re a fan of the sciences or the art world, Chicago has a world class museum scene with lots of options for museum-goers to choose from.

Head to Chicago’s museum campus to check off three famous Chicago museums in one go. Explore marine life at the Shedd Aquarium, head to America’s first planetarium to learn about all things space, and then stop by The Field Museum to examine natural phenomenons and Earth’s history.

For a taste of Chicago’s fine arts scene, head to the Art Institute of Chicago, consistently ranked the top museum in America, the Museum of Contemporary Art for a look at art and the industry as a whole, or check out the Chicago Architecture Foundation to get an in-depth look and understanding of Chicago’s cutting-edge architecture industry.

Winter Wonderfest at Navy Pier


The much anticipated PNC Bank Winter WonderFest features endless indoor seasonal winter fun with over 24 rides, slides, and even an indoor skating rink. Along with rides and activities, visitors can also expect lots of live entertainment and festive foods.

Attractions at Wonderfest include:

  • Arctic Ice Skating Rink: lined with Christmas trees, banners, and white lights, this festive rink attracts visitors throughout the season.
  • Extreme Ice Trail Ropes Course: maneuver your way across beams, staircases, and platforms while making your way through a course that stretches 27.5 feet in the air. Remember to dress appropriately–no heels, skirts, or dresses allowed.
  • Ferris Wheel: get a view of Winter Wonderfest from the top of the 50-foot high indoor Ferris Wheel.
  • Zero Gravity: brave riders will be held to the wall by the force of gravity as the ride spins faster and faster, finally lifting riders into the air at a 45-degree angle as it continues to spin.
  • Polar Extreme: race through a frozen tundra to escape via slide on the other side of this course.
  • Ice Peaks Climbing Wall: lace up your gym shoes and test your upper body strength on this interactive climbing wall.

Other popular attractions include the Cliff Hanger, Kringle Carousel, the Snowy Summit Climbing Wall, Lighthouse, the Reindeer Express Train Ride, and several slides and obstacle courses.

Insider tip: check online for more information and to save on tickets in advance.

Polar Adventure Days

Head to Polar Adventure Days for Outdoor Winter Fun and All Things Nature

Photo credit: Polar Adventure Days

When: December 12, 2015, January 23, 2016, and February 20, 2016 from noon-4 pm

Geared towards kids, Northerly Island’s Polar Adventure Days features lots of fascinating fun, including meet and greets with Siberian huskies, ice sculpture creations, storytelling, live music, and more.

In its 11th year, the Adventure Days are perfect for the entire family and a big hit in the Chicago area.

While you’re there, check out some of the other attractions on Northerly Island such as the Adler Planetarium, Chicago’s oldest planetarium, to learn more about space exploration.

Chicago Sketch Comedy Festival

The world's largest sketch comedy festival takes place in Chicago January 2016

Photo credit: Stage 773’s Official Facebook Page

When: January 7-17, 2016

You haven’t truly experienced Chicago without checking out its famous theater scene.

The Chicago Sketch Comedy Festival is the world’s largest sketch comedy festival bringing 165 groups, 186 shows, and 8 days packed with some of the world’s best talent.

Tour the Chicago Theatre

Go on a tour of the famous Chicago Theatre

Fans of the performing arts will also enjoy going on a behind-the-scenes, historic tour of the famous Chicago Theatre.

You’ll get to know the ins and outs and the rich history of the very stage that has hosted stars such as Dolly Parton, Dean Martin, Frank Sinatra, and more since its opening in 1921.

Donut Fest

Looking for something to do this winter in Chicago? Go to Donut Fest.

When: January 31, 2016

If you love sugar and dough, and sugary doughy combinations, you don’t want to miss Donut Fest, a fun and entertaining celebration of donuts and other baked goods in all of their sweet, sweet glory.

Check online for a list of vendors and to buy tickets.

Chicago’s Best Wingfest


When: February 13, 2016

For an endless selection of Chicago’s best wings, live entertainment, prizes, and more, head to Chicago’s Best Wingfest.

The best wings will be awarded the title of “Best of Fest” and are judged based on appearance, aroma, and taste in ten categories. Judges are chosen randomly from the crowd so you could be picked!

Save on Attraction Admission 

Whether you’re visiting Chicago on a solo trip or traveling with all your kids in tow, be sure to check out these things to do in Chicago in the winter for seasonal fun and a unique Chicago experience.

And remember, a Go Chicago Card All-Inclusive Pass can save you big on admission to many of these attractions.

Go Chicago Card

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