8 Things to Do in Chicago This Winter

The 2017 Farmers’ Almanac is predicting a frigid, snowy winter, but we’re not going to let that stop us from exploring our incredible city! Indoors or out, Chicago has plenty to offer throughout the cold, dark months. To give you some inspiration, here are 8 things to do in Chicago this winter.

8 Things to Do in Chicago This Winter

Ride the CTA Holiday Train

In 1992, the CTA posted a holiday sign in front of an out-of-service train that was used to deliver food donations to charities throughout Chicago. 25 years later that sign has evolved into festive train cars (and buses) covered in lights and carrying Santa and a new Elves’ Workshop Train.

If you’d like to catch a ride on the CTA Holiday Train, check out the schedule online to find out when the train is running. Grab a photo as it pulls into the station but don’t miss your chance to hop on!

Holiday Train

Watch a Play

Chicago has a great theater scene and winter presents the perfect opportunity for a night out for dinner and a show. Check out Theatre in Chicago or Broadway in Chicago to see what’s currently playing. We’re looking forward to seeing Hamilton in 2017!

Visit the Christkindlmarket

A German holiday tradition, the Christkindlmarket runs from November 18 – December 24 in Daley Plaza. The event is free to attend, and you’ll find unique gifts, typical German food and drinks, and entertainment. If you get cold, find the festival tent in the Northwest corner for a warmer spot to grab a drink.


Go Ice Skating

There are plenty of places to go ice skating around Chicago, but our favorites are the Skating Ribbon at Maggie Daley Park and The Peninsula Sky Rink. The Skating Ribbon is not your typical round ice rink but winds through the park. Admission is free and skate rentals are $12-14. The Sky Rink is located four stories above Michigan Avenue and provides a unique outdoor venue for skating. Admission is a suggested donation of $15 that benefits Lurie Children’s Hospital and Hephzibah.

Run a 5k or Half Marathon

If you need some extra motivation to stay active through the holidays, sign up for a winter race! The F^3 Lake Half Marathon & 5K is held on Chicago’s lakefront on January 28. You can find other races at Running in the USA.

See the Lights at the Lincoln Park Zoo

The Lincoln Park Zoo is lit up with twinkling lights and Christmas music every year for the family-friendly ZooLights. You can see the lights (for free!) most evenings from 4:30-9pm through January 1, 2017. All of the animal exhibits are also open during the event. Don’t miss the new penguin and polar bear exhibits!


Visit the Art Institute

The Art Institute of Chicago makes a great winter activity and has something for everyone. It was voted the number one museum in the world in 2014 (currently #2) and is a must do in Chicago. Residents of Illinois receive free general admission every Thursday from 5-8pm.

Snowshoe or Ski at Morton Arboretum

Morton Arboretum is located an hour west of downtown Chicago and open sunrise to sunset 365 days a year. If the forecasts prove true, snowshoes and cross country skis are available for rent from the Visitor Center when there is at least 4″ of snow on the ground.  If there’s not enough snow, check out the hiking, biking and running options.

things to do in chicago this winter

Do you love or hate winter? What are you favorite activities in the cold months of the year?

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