Fun winter activities in Chicago

Winter is one of the best seasons to visit Chicago. Locals and visitors alike embrace the cold and take to the streets for ice skating, curling and snapping photos of a beautiful city covered in snow. And there are so many more fun Chicago winter activities in store this year, both outside and indoors. Use this guide to start planning your adventures around Chicago, and don’t miss our tips for staying warm when the temperatures drop below freezing. 

Top 5 things to do in Chicago during winter 

1. Stroll German-inspired Christmas markets

The city hosts Christkindlmarket in three locations: Daley Plaza in the Loop, Gallagher Way in Wrigleyville and RiverEdge Park in Aurora. Shop for handcrafted gifts under twinkling holiday lights, keeping warm with a mug of Glühwein (spiced wine) and nibbling on sweet treats or, better yet, a steaming bratwurst. 

2. Hit the ice more than once

One of the undisputed top Chicago winter activities is ice skating outdoors. With its towering skyscrapers and the famous Cloud Gate (the Bean) sculpture, Millennium Park Ice Rink is the obvious choice. But for something a little different, head to the Maggie Daley Park Skating Ribbon, where you can glide along a winding path that cuts through snow-dusted trees. Or try the Peninsula Sky Rink if you fancy a spin atop a hotel with stunning views of the bustling city below. 

3. Play ‘chess on ice’ over drinks 

When Chicago freezes over, it means that curling season has arrived. This sport involves players sweeping curling brooms to slide granite stones over ice toward a target. And when you play with drinks, the sport is not only a ton of fun, but a great way to make new friends in Chicago. Outdoor curling spaces include Upstairs at The Gwen, Kaiser Tiger, Kennedy Rooftop and Harry Caray’s Tavern at Navy Pier.

4. Channel your inner child with a day of sledding 

You can pretty much bet on snow in Chicago during the winter months, so drop your devices and pick up a sled instead. The city has many sledding hills that are easily reached by car. Caldwell Woods is probably the best choice — plus, it’s a stone’s throw from Superdawg, one of the best hot dog places in Chicago. Soldier Field, on the other hand, has stunning views of Lake Michigan. And if sledding is not your thing, strap on snowshoes and hit the nature trails of Northerly Island, which open up to a panorama of the Chicago skyline. 

5. ‍Explore Chicago’s architecture and public art spaces

Throw on those layers and set out to marvel at Chicago’s plethora of landmarks, like the Museum of Science and Industry, Chicago Theatre, Willis Tower and the Wrigley Building, made all the more dramatic when topped with snow. Or track down colorful large-scale murals and street art found on bridges, buildings and train stations in the Wabash Arts Corridor and Pilsen. Then hop in your car to Oak Park, a Chicago suburb that is home to more Frank Lloyd Wright buildings than anywhere else in the world.

4 best indoor activities in Chicago

1. ‍Admire or play with art 

Roaming the halls of the city’s rich museum offerings may be one of the best things to do in Chicago during winter if you want to escape the snow for a bit. The Art Institute of Chicago, Museum Of Contemporary Art Chicago, Chicago History Museum and Field Museum are certainly unmissable. But if art and history still leave you feeling cold, then check the delicious multi-sensory installations of the new Museum of Ice Cream or the interactive and immersive experiences of the Color Factory, another recent addition to Chicago’s long list of amazing museums.  

2. Find warm weather landscapes under glass

If you were to put the colors, scents, sounds and temperature of the tropics in a glass jewelry box, the Garfield Park Conservatory would be it. The eight lush indoor display gardens, complete with a water lily pond, are a feast for the senses that make the cold winter seem months away. The Lincoln Park Conservatory is another excellent option, featuring four exotic plant displays: Palm House, Fern Room, Orchid House and Show House.

3. Stay warm while restaurant hopping 

From deep-dish pizza at Pequod’s and hotdogs at Portillo’s to Italian beef at Al’s, sampling the city’s slew of iconic (and hearty) dishes is one of the best Chicago winter activities to stay warm while satisfying your hunger. Beyond the classics, the culinary offerings here are as diverse as those who make Chicago their home, so don’t pass on tamales from The Tamale Guy or pierogi at Podhalanka, either. Those with more discerning palates will be glad to know that in 2022, the prestigious Michelin Guide awarded 21 Chicago restaurants with Michelin star honors, including four new restaurants (Porto, Kasama, Esmé and Galit). The 2023 list will be announced in November, so keep an eye out for an update on the city’s top restaurants. 

4. Take refuge in an igloo 

Though winter may bring howling wind and swirling snow, Chicagoans are not giving up outdoor dining or their love of rooftops. And between the domes, igloos and fire pits, you will find plenty of options to dine, drink and be merry even as the temperature drops. Among the city’s standout options are London House, Kennedy Rooftop and Joy District.

Tips for staying warm in Chicago in winter

Before you start checking off your list of fun things to do in Chicago during winter, you’ll want to take note of these tips to stay warm.  

Don’t bulk up 

Heavy sweaters and jackets are not likely to keep you warm nor comfortable. Instead, pack plenty of layers, like thin fleeces, merino wool and silk to keep you both cozy and agile.

Keep the heat in your feet

Staying warm starts with your feet, so choose weatherproof and waterproof footwear with a thick but flexible sole, especially if you plan on walking a lot or participating in winter sports. 

Materials matter

Chicago winters are both cold and windy, so make sure your winter coat’s outer layer is made specifically to withstand high winds, heavy snow or rain. 

Make the most of your time in Chicago

Consider renting a car in Chicago to get to and from all the fun winter activities. It’ll keep you warmer longer and make it easy to do more in less time. With Avail car sharing’s convenient self-service neighborhood locations, you can book online in minutes and pick up your car without waiting in a single line. When you borrow a car from Avail, you’ll be using a local Chicagoan’s car to get around and thereby supporting the local community. Allstate insurance protection and 24/7 roadside assistance are available for every trip. Talk about not being left out in the cold!