Although Chicago has plenty of famous locations and special winter events to keep your mind off the temperature, some things are even better in the cold! Among your choices are winter festivals, holiday markets selling goods from around the world, and ice rinks galore. Read on for our favorite Chicago winter activities, and be sure to check out the family-friendly event options at the Willis Tower Skydeck!


It’s hard to imagine a better harbinger of the holiday season than the annual CHRISTKINDLMARKT. Inspired by the 16th-century Christkindlesmarkt in Nuremberg, Germany, this outdoor market is a goldmine for its vendors’ high-quality gifts and food. Start out with your choice from dozens of spiced roasted nuts, and the classic Christkindlmarket mug of mulled wine — and keep the mug as a souvenir! Then, tour the market to check out wool and alpaca knits, handmade cuckoo clocks, ornaments, gourmet chocolates, and more. Try the potato latkes for dinner!

Address: 50 W Washington St, Chicago, IL 60602

Date: Opens November 22

Christkindlmarket Things to Do in Chicago in the Winter


For a SKATING EXPERIENCE that’s outside the rink, how about the Maggie Daley Skating… Ribbon? The SKATING EXPERIENCE AT MAGGIE DALEY is dramatically different from the usual ice rink, with the surrounding scenery changing constantly as you wind through the landscape. Best of all, admission is free, and skates are available to rent for just $13 Mon – Thurs, or $15 Fri – Sun and holidays.

Address: 337 E Randolph St, Chicago, IL 60601

Date: Open in temperatures under 50 degrees Fahrenheit

Skatting-Ribbon-at-Maggie-Daley-Park Things to Do in Chicago in the Winter


This one-of-a-kind FESTIVE HOLIDAY EXPERIENCE is a kid favorite. Celebrate 25 years for the Lincoln Park Zoo with hundreds of LUMINOUS DISPLAYS and seasonal activities. General admission is free, with optional tickets available to purchase for events, including the Holiday Market, Adults’ Night Holidaze, and BrewLights Presented by Louis Glunz Beer, and Zoo Years’ Eve.

Address: 2001 N Clark St, Chicago, IL

Date: Nov 29 – January 5

ZooLights Things to Do in Chicago in the Winter


This annual event is one of best-known fun things to do in Chicago in the winter. Each year,  170,000 square feet at Navy Pier is packed with giant slides, inflatable rides, a festive carousel, holiday-themed activities, indoor ice skating, and much more. Buy tickets early to save on admission!

Address: 600 E Grand Ave, Chicago, IL

Date: Friday, December 6, 2019 – Sunday, January 12, 2020

Winter-Wonderfest-1024x506-1 Things to Do in Chicago in the Winter

Learn More About the Best Chicago Winter Activities

Don’t hesitate to contact us if you have further questions about Chicago winter events. For spectacular views of snowbound Chicago, try the 109th floor of the Willis Tower. Then, drop down to the 66th and 67th floors to try The Metropolitan — one of the best places to eat in and around Willis Tower. The Skydeck is available for small or large groups, as well as private events. Check out ticket options to plan your trip today!

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