Tis the season to celebrate in the city! Whether you’re looking for free experiences or fun for the whole family, there’s a never-ending list of wonderful sites to see and things to do this winter in Chicago. We’ve narrowed it down to our top five picks you won’t want to skip out on this holiday season. See below for all the details!


{ Ice Skating at Millennium Park } 

Skaters of all ages are invited to take a spin on the ice at the McCormick Tribune Ice Rink at Millenium Park during its 18th season of this yearly tradition! Skating is free and skate rentals and lockers are available for use at the rink. For those new to skating, free lessons are even available on Fridays, Saturdays, and Sundays one hour before the skating rink opens! With the rink open until March (weather permitting), there’s tons of opportunity to enjoy this free winter activity in the city.

Cost: Free!
When: November 16th, 2018 – March 10, 2019
Where: McCormick Tribune Ice Rink
More Information Here


{ Fifth Third Bank Winter Wonderfest } 

With over 170,000 square feet of fun to enjoy, the 18th annual Fifth Third Bank Winter Wonderfest at Navy Pier has an impressive roster of attractions, photo ops, activities, and holiday decor for the whole family to enjoy! Be sure to check their event calendar for special things happening all month long.

When: November 30th, 2018 – January 6th, 2019
Where: Navy Pier
More Information Here


{ The Nutcracker } 



The House Theatre of Chicago has reimagined The Nutcracker with an original, ballet-free show that continues to garner rave reviews from the likes of Chicago Tribune and Chicago Sun Times. The show is beautifully choreographed, fast-paced, family friendly, and enjoyable for all!

When: November 9th – December 30th, 2018
Where: Chopin Theatre
More Information Here


{ ZooLights at Lincoln Park Zoo } 

For the 24th year in a row, experience the glow of over 2.5 million lights in this seasonal celebration at the Lincoln Park Zoo! The ZooLights event is available on select dates through the first week of January and offers free family-friendly fun with beautiful light displays and activities for all.  

When: Select Dates November 23rd, 2018 – January 6th, 2019
Where: Lincoln Park Zoo
More Information Here


{ Christkindlmarket } 



Through December 24th, enjoy the 24th annual Christkindlmarket at Daley Plaza which brings German and European traditions to Chicago with a festive open-air festival. The unique experience offers German food and drink and diverse holiday entertainment and has become a staple of the season in Chicago. The best part? It’s always free!

When: November 16th – December 24th, 2018
Where: Daley Plaza in the Chicago Loop
More Information Here