Things To Do In Chicago In Winter: How To Best Spend Your Time

CuddlyNest Team

Published June 6, 2024 | Updated April 30, 2026Jun 6, 2024

4 min read

Frequently asked questions about things to do in chicago in winter

What are some outdoor activities I can do in Chicago in winter?

<ul> <li>Ice skating at Millennium Park or Maggie Daley Park</li> <li>Curling outdoors or on a rooftop rink</li> <li>Sledding at Soldier Field</li> <li>Exploring Millennium Park and the surrounding area</li> <li>Walking or running along the lakefront trail with stunning views of the city</li> <li>Visiting Lincoln Park Zoo to see the animals in their winter coats</li> </ul>

What are some things to do indoors in Chicago in winter?

<ul> <li>Explore the world-renowned collections at the Art Institute of Chicago</li> <li>Learn about natural history at the Field Museum</li> <li>See underwater creatures at the Shedd Aquarium</li> <li>Visit the Museum of Science and Industry for interactive exhibits</li> <li>Catch a concert or a play at one of Chicago's many theaters</li> </ul>

What are some free things to do in Chicago in winter?

CuddlyNest Team

CuddlyNest is the world's largest vacation rental search engine, comparing millions of accommodations across 200+ booking sites. Our editorial team of seasoned travelers and local experts shares insider tips, destination guides, and travel inspiration to help you plan the perfect trip — whether you're booking a cozy cabin, a beachfront villa, or an apartment in the heart of the city.

Our Editorial Policy More articles by CuddlyNest Team

Blog/Travel

Travel is for
everyone.

Just because winter is here doesn’t mean you have to stay cooped up in your house. In fact, there are plenty of activities to do in the winter that will keep you busy. Here are some fun and cozy things to do in Chicago in winter.

Quick Jumplinks

Embrace the outdoors

Bundle up and enjoy wintery activities like ice skating at Millennium Park or Maggie Daley Park, curling outdoors or on a rooftop rink, or sledding at Soldier Field. You can also take a walk or bike ride along the lakefront trail and enjoy the stunning views of the city skyline.

Explore world-class museums and attractions

Chicago has some of the best museums in the world and they are great places to escape the cold. The Art Institute of Chicago, the Field Museum of Natural History, the Shedd Aquarium, and the Museum of Science and Industry are all must-sees. You can also check out the Willis Tower for breathtaking views of the city, or take a trip to Navy Pier for some shopping, dining, and entertainment.

Warm up with a delicious meal

Chicago is a foodie paradise, and there's no shortage of great places to eat. In the winter, you might be especially craving some hearty comfort food. Try some Chicago-style deep-dish pizza, a juicy Italian beef sandwich, or a classic Chicago-style hot dog.

Immerse yourself in the holiday spirit

Chicago goes all out for the holidays, with festive decorations, twinkling lights, and special events. Visit Christkindlmarket in Daley Plaza for a traditional German Christmas market experience replete with handcrafted ornaments, delicious food, and glühwein (mulled wine). You can also take a drive or walk through some of the city's most famous neighborhoods like Lincoln Park, Wicker Park, and Bucktown to see their elaborate holiday light displays.

Catch a show

Chicago has a vibrant theater scene, with everything from Broadway shows to off-beat productions. You can also catch a concert, a sporting event, or a festive comedy show.

What type of winter, snowy fun will your family have this year? Share your ideas to spread the Christmas spirit with us and our readers.