Chicago is a must-visit destination all year round — but there’s something particularly magical about winter time. The snow-dusted city is filled with things to do, including rooftop curling, toasty pop-up saunas, and cozy bars and restaurants. It’s also a time of year when culture shines, with an endless array of museum exhibits, live performances, and beyond.
Dust off that cabin fever and come discover your Chicago winter adventure.
Jan. 23 – Feb. 8, 2026
It’s the best time of year to experience Chicago’s award-winning dining scene. Search special deals at hundreds of acclaimed restaurants during Chicago Restaurant Week.
Feb. 5 – 15, 2026
11 days, hundreds of amazing shows. Score discounted tickets to dramas, comedies, musicals, and more during the highly anticipated Chicago Theatre Week.
Feb. 7 – 16, 2026
The nation’s longest-running auto show has been a Chicago tradition for more than 120 years, bringing hundreds of vehicles, activations, and events for car lovers of all ages.
Experience an only-in-Chicago winter with these unique indoor and outdoor activities.
Various venues
Ramova Theatre
Various venues
Chicago Botanic Garden
Big Marsh Park
Chinatown
Honor Black History Month in Chicago with can’t-miss exhibits, performances, concerts, plays, tours, and more events this February.
Discover Black history in Chicago
Rooftop bar season is year-round in Chicago. Check out these cozy winter spaces featuring igloos, fireplaces, curling rinks, and more.
Find winter rooftop barsChicago offers the perfect mix of big-city romance and cozy winter vibes. Here’s our guide to planning the perfect Valentine’s Day, from candlelit restaurants to unforgettable activities.
Start planning your date night in Chicago
Chicagoans never let a little cold slow us down. Winter is packed with endless things to do, including snowshoeing, cross country skiing, comedy shows, art exhibits, unique cultural events, and so much more.
Explore our winter guide to Chicago
