The ultimate guide to enjoying a Chicago winter

The ultimate guide to enjoying a Chicago winter

Chicago knows a thing or two about cold weather. And come winter, when a blanket of snow covers everything and the air is biting cold, you can count on the city to offer residents and visitors plenty of fun winter outdoor activities. And if things get a little too cold for comfort, you’ll still find plenty of fun stuff to do indoors. Bundle up, because you’re in Chicago — and you’re in for an exciting winter wonderland escape.

Chicago’s best winter outdoor activities

Get into the holiday spirit at German-inspired Christmas markets

The city hosts Christkindlmarkt in three locations: Daley Plaza, 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 yummy treats or, better yet, a steaming bratwurst. 

Aerial view of Maggie Daley Park Skating Ribbon, where people are ice skating in a winding path lined by trees.

Hit the ice more than once

With its towering skyscrapers and the famous Cloud Gate (the Bean) sculpture, Millennium Park is the obvious choice. But for something a little different, head to 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. 

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 Chicago Theatre, Aqua and Willis Towers, the Wrigley Building and the Art Institute of Chicago, 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.

Play ‘chess on ice’ over drinks 

When Chicago freezes over, it means that curling season is here. 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.

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. 

Best indoor activities in Chicago

Admire or play with art 

Roaming the halls of Chicago’s rich museum offerings may be one of the best ways to stay warm in Chicago. 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 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.  

Indoor view of the Garfield Park Conservatory in Chicago, with a variety of trees below a glass-and-steel gable roof.

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.

Stay warm 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 ways to stay warm in Chicago. Beyond the classics, the culinary offerings here are as diverse as those who made Chicago their home, so don’t pass on tamales from 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 23 Chicago restaurants with Michelin star honors, including four new restaurants (Claudia, Kasama, Esmé and Galit). 

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 visiting Chicago in winter

Before you start checking off your list of fun stuff to do in winter in Chicago, you’ll want to add these tips to stay warm.  

Don’t bulk up: Heavy sweaters and jackets are not likely to keep you warm or 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: Keeping warm starts with your feet, so choose weatherproof and waterproof footwear with a thick but flexible sole, especially if you plan on walking 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. 

Want to stay warm and make the most of your time in Chicago? 

Consider renting a car to get you to and from all the fun winter activities in Chicago. With Avail car sharing’s airport and convenient neighborhood pick-up locations, you can book online in minutes and skip the long lines and endless paperwork at the car rental counter. When you borrow a car from Avail, you’ll be using a car from a local car owner that comes with 24/7 roadside assistance and Allstate insurance coverage at no additional cost. Talk about not being left out in the cold!