Although Chicago has plenty of famous locations and seasonal attractions to enjoy year round, winter brings a unique lineup of experiences worth planning around. From festive markets and outdoor skating to iconic indoor attractions, there are no shortages of memorable things to do in Chicago in winter. Below, explore some of the best Chicago winter activities, and be sure to check out the family-friendly event options at the Willis Tower Skydeck.

CHRISTKINDLMARKET CHICAGO

It’s hard to imagine a better way to kick off the holiday season than the annual CHRISTKINDLMARKT. Inspired by the 16th-century Christkindlesmarkt in Nuremberg, Germany, this beloved Chicago winter activity features dozens of vendors offering handcrafted gifts, seasonal décor, and traditional food. Snack on spiced roasted nuts, sip mulled wine in a collectible mug, and browse wool knits, ornaments, gourmet chocolates, and more. Don’t miss the potato latkes.

Address: 50 W Washington St, Chicago, IL 60602

Date: Opens November 21, 2025

MAGGIE DALEY PARK SKATING RIBBON

For a skating experience unlike a traditional rink, the SKATING EXPERIENCE AT MAGGIE DALEY offers a scenic winter activity in the heart of the city. The winding ribbon layout provides constantly changing views as skaters glide through the park. Admission is free, with skate rentals available for $13 Monday through Thursday or $15 Friday through Sunday and holidays.

Address: 337 E Randolph St, Chicago, IL 60601

Date: Open in temperatures under 50 degrees Fahrenheit

LINCOLN PARK ZOOLIGHTS FESTIVAL

This one-of-a-kind FESTIVE HOLIDAY EXPERIENCE is a seasonal favorite for families visiting Chicago in winter. Lincoln Park Zoo celebrates the season with hundreds of LUMINOUS DISPLAYS, interactive activities, and themed events. General admission is free, with ticketed options available for the Holiday Market, Adults’ Night Holidaze, BrewLights Presented by Louis Glunz Beer, and Zoo Years’ Eve.

Address: 2001 N Clark St, Chicago, IL

Date: Nov 21, 2025 – January 4, 2026

CHICAGO WINTER WONDERFEST AT NAVY PIER

One of the most well-known things to do in Chicago in winter, Winter WonderFest transforms Navy Pier into an indoor seasonal playground. More than 170,000 square feet are filled with giant slides, inflatable rides, a festive carousel, holiday themed attractions, and indoor ice skating. Purchasing tickets in advance is recommended to secure the best pricing.

Address: 600 E Grand Ave, Chicago, IL

Date: December 5, 2025 – January 4, 2026

Learn More About the Best Chicago Winter Activities

If you have questions about Chicago winter events or seasonal attractions, don’t hesitate to contact us. For sweeping winter views of the city, visit the 109th floor of the Willis Tower at Skydeck Chicago. Afterward, head to the 66th and 67th floors to experience The Metropolitan, one of the best places to eat in and around Willis Tower. Skydeck is available for small or large groups, as well as private events. Explore ticket options to plan your winter visit.

Frequently Asked Questions About Things to Do in Chicago in Winter

What are the best things to do in Chicago in winter?

Some of the best things to do in Chicago in winter include visiting holiday markets like Christkindlmarket, ice skating at Maggie Daley Park, attending Lincoln Park ZooLights, and exploring indoor attractions such as Skydeck Chicago at Willis Tower.

Are there indoor activities in Chicago during winter?

Yes. Chicago offers many indoor winter activities, including museums, seasonal exhibits, dining experiences, and observation decks like Skydeck Chicago, which provides panoramic city views year round regardless of weather.

Is Chicago worth visiting in the winter?

Chicago is worth visiting in the winter for travelers looking to experience festive events, fewer crowds, seasonal attractions, and iconic city views. Many popular things to do in Chicago in winter are indoors or designed to embrace the cold weather.

Image sources:
http://www.christkindlmarket.com/
https://maggiedaleypark.com/things-to-do-see/skating-ribbon/
https://www.lpzoo.org/
https://navypier.org/