20 Fun And Unique Things To Do This Winter In Chicago

The weather outside may be frightful, but I guarantee that you’ll still find something to do in Chicago that is delightful. From ice skating under bright lights in The Loop to sampling wines and cocktails at a local bar, this guide has free and interesting things to do in and around the city of Chicago for you to enjoy all winter long.

Note: Starting on January 3rd, Cook County and the city of Chicago will require all individuals age 5 and older to show proof of vaccination to dine indoors, visit gyms, or enjoy entertainment venues where food or drink is being served. Be sure to keep yourself and others safe by following the latest mandates and guidelines concerning COVID-19.


WINTER activities

Ice skating in Millennium Park

1. Skate the ice rink in Millennium Park—or other neighborhood park district rinks.

2. Discover emerging artists at a gallery opening.

3. Take insta-worthy photos at an experiential museum.

4. Escape to an indoor botanical garden at the Garfield Park Conservatory.

5. Cook a stew, chili, or soup from scratch.

6. Rent a cozy cabin in a popular Midwest ski town.

7. Spend a week in the tropical city of Miami, thanks to this expert guide.

8. Volunteer for a grassroots organization.

9. Order take out, pick-up, or delivery from a neighborhood restaurant.

MLK Day performance by the Chicago Sinfonietta at the Chicago Symphony Orchestra

10. Watch live performances at Chicagoland theaters.

11. Go sledding with kids of all ages on hills around Chicagoland.

12. Celebrate Black History Month in February, and all year long.

13. Binge watch a new t.v show.

14. Walk among snow-covered trees at an arboretum or state park in Illinois.

15. Explore a Winterland at Gallagher Way in Wrigleyville.

16. Uncover a hidden speakeasy or secret bar.

17. Try something new and interesting during an at-home date night.

Interior of Provisions wine bar in the Uptown neighborhood of Chicago

18. Shop small and local in a Chicago neighborhood.

19. Sample wines at a local store or specialty bar.

20. Cheer for the Bulls or Blackhawks at the United Center.


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