While the temperature might drop, Chicago has a way of turning up the heat with exciting cultural happenings, world-class dining, and unexpected events.
Come experience the one-of-a-kind warmth of the country’s Best Big City.
Christkindlmarket
Winter in Chicago
The Warmest City
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Chicago holiday traditions
Nowhere does the holiday season quite like Chicago.
Celebrate this magical time of year with Chicago’s most luminous lights shows, outdoor ice skating, festive shows, Christmas markets, and more holiday traditions.
Explore our holiday guide to Chicago
Winter rooftops
Rooftop bar season is year-round in Chicago.
Check out these cozy winter rooftops with scenic city views, personal igloos, outdoor fireplaces, curling rinks, and more.
Find winter rooftop bars
Unique winter activities
Experience a one-of-a-kind winter getaway in Chicago this year.
Plan your trip with our winter bucket list, featuring hidden gems, local favorites, and more unique things to do this holiday season and beyond.
Explore the Chicago winter bucket listPlan your trip
Cozy neighborhood spots Chicago
More things to do in Chicago this winter
Chicago Restaurant Week
Jan. 22 – Feb. 7, 2027
It’s the best time of year to experience Chicago’s award-winning dining scene. Find special menus at hundreds of acclaimed restaurants during Chicago Restaurant Week.
Chicago Theatre Week
11 days, hundreds of amazing shows. Score discounted tickets to dramas, comedies, musicals, and more during the highly anticipated Chicago Theatre Week.
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