10 Things to Do in Chicago in the Winter to Keep Yourself Active

There’s no reason to stay cooped up all winter! While Chicago winters make it tempting to be a couch potato until spring, the Windy City has no shortage of fun indoor and outdoor activities for all ages. Here are 10 of our favorite winter activities in Chicago you should try this year to have an active and fun winter!

Christmas Around the World Exhibit

5700 S Lake Shore Dr, Chicago, IL 60637

WHEN: Nov. 17 – Jan. 3


Christmas Around the World and Holidays of Light at the Museum of Science and Industry is a one-of-a-kind experience. The Christmas exhibit began with a single tree in 1942 and has since grown into a forest of more than 50 trees and displays decorated to represent the holiday traditions and cultures around the world.

This year’s theme is the golden age of travel with a spotlight on the museum’s Pioneer Zephyr train and Take Flight’s 727. Patrons can also visit and pose with Santa in a festive photo studio in the museum’s holiday store. Tickets are available now. Don’t miss the lighting of the museum’s four-story Grand Tree on Nov. 17!


Tree Lighting Ceremony

201 E Randolph St, Chicago, IL 60602


WHEN: Nov. 19 thru Jan. 9

The Tree Lighting Ceremony for Chicago’s official Christmas tree was virtual in 2020, but returns for in-person dazzling Friday, Nov. 19. If you are looking for things to do in the city for the winter season, the ceremony starts at 6 p.m. with the actual lighting occurring at approximately 6:30 p.m. Fireworks and a special concert headlined by singer-songwriter Brian McKnight will follow at 6:35 p.m.


This year, the event has been reimagined and expanded. There will be multiple viewing locations with screens and concessions across the park and a main stage on the Great Lawn. If you miss the ceremony, the 51-foot Blue Spruce will still be shining brightly daily until Jan. 9.

World’s Tiniest Tree Lot

2952 W Armitage Ave, Chicago, IL 60647

WHEN: Saturday, December 11, 3:00 pm to 7:00 pm

Big on holiday spirit, tiny on trees – join Half Past and Parson’s Chicken & Fish for the World’s Tiniest Tree Lot on Saturday, December 11 in support of Love Fridge, a Chicago mutual aid group grounded in food justice. Stop by for an expansive array of complimentary mini Christmas trees, Santa Claus photo ops and mini ornament decorating, as well as plenty of Chicago’s favorite fried chicken and Half Past.

Ice Skating

337 E Randolph St, Chicago, IL 60601

WHEN: Nov. 19 – Mar. 13

One of the joys of winter in Chicago is outdoor ice skating—it’s a classic snow globe scenario after all! Nothing beats the skating ribbon at Maggie Daley Park, where you’ll get city views and a quarter-mile path to loop around.

This season has a nice bonus with Gogh Skating, a Vincent van Gogh experience brought to you by Immersive Van Gogh and the Chicago Park District. Immersive Van Gogh had a successful exhibit in Chicago this year and although its stop in the city ended in September, the magic continues on the skating ribbon.

The themed experience lets skaters glide across Van Gogh-inspired visuals, like “Starry Night” and “Sunflowers.” Reserve your spot today!


50 W Washington St, Chicago, IL 60602

3635 N Clark St, Chicago, IL 60613


  • Christkindlmarket Chicago, Nov. 19 – Dec. 24
  • Christkindlmarket Wrigleyville, Nov. 19 – Dec. 31

Christkindlmarket offers a unique holiday shopping experience for residents in Chicago with tents selling crepes, bratwurst, fresh pretzels, ornaments, and other festive gifts all in an open-air market. This traditional winter holiday market is one of the most authentic of its kind outside of Europe.

This year celebrates Christkindlmarket’s 25th anniversary and the debut of special annual mugs and a new ornament. Fill your mugs with mulled wine and cheer on the start of the holiday season!


2200 N Cannon Dr, Chicago, IL 60614

WHEN: Nov. 19 thru Jan. 2

This fun, family-friendly Chicago tradition features hundreds of dynamic LED displays and dazzling lights in the shape of animals, trees, and more to create a twinkling winter wonderland.

There are also festive events like visits with Santa, a holiday pop-up bar, an enchanted forest, a light maze, and concerts. Reservations are required and tickets are available now—Mondays and Tuesdays are free!

Millennium Park Holiday Sing-Along

201 E Randolph St, Chicago, IL 60602

WHEN: Nov. 26 thru Dec. 17

Put your karaoke chops to the test with the new Millennium Park Holiday Sing-Along series, previously “Caroling at Cloud Gate.” The winter event in Chicago has been reimagined to be more inclusive of different backgrounds, cultures, and holiday music traditions.

Sing your heart out before Happy Hour Fridays at 6:00 pm, Nov. 26 to Dec. 17, and Sunday, Dec. 12.

TBOX Bar Crawl

WHEN: Dec. 11

TBOX, the world’s largest holiday bar crawl, returns in December for its 25th anniversary. This Chicago party tradition has hardcore partiers travel through 30 Wrigleyville bars from 10:30 am to 7:00 pm. Additionally, to make up for its 2020 hiatus, this year’s TBOX theme is “Back to the 90s” with a celebration of the music, fashion, movies, and culture of everything from the decade. 

Get your tickets now—proceeds support local Chicago and Lakeview charities as well as The Lakeview East Community Partnership.

Cupid’s Undie Run

3540 N Clark St, Chicago, IL 60657

WHEN: Feb. 19

Who strips down to their underwear in the dead of winter and runs? Every February, thousands across the U.S. do. Cupid’s Undie Run supports those affected by neurofibromatosis, a rare genetic disorder that causes tumors to grow on nerves throughout the body.

This mile(ish) run starts with drinking and dancing at Sluggers World Class Sports Bar and ends with a dance party to get your body heat rising. Registration is now open.

Outdoor Curling

1415 W Randolph St, Chicago, IL 60607

The Winter Olympics aren’t until February, but you can channel your inner athlete with outdoor curling right in the city. Kaiser Tiger has three ice curling lanes in their spacious beer garden.

The sausage, bacon, and beer-focusing gastropub has hearty eats and tons of brews on tap to keep you warm all winter long.

Sledding at Soldier Field

1410 Special Olympics Dr, Chicago, IL 60605

We may be in the flat Midwest, but you can still catch some thrilling heights right here in the city. The Soldier Field Sledding Hill located on parkland outside the stadium features a 33-foot slope with city views.

The Chicago Park District even makes faux snow when there isn’t enough, so you’ll always be whooshing down a white and fluffy hill. Snowball fights, snowmen, and snow angels are also welcome—just watch out for the sleds!