Things to Do in Chicago with Kids During Winter Break

During the 2021 winter break, enjoy the Serenity Winter Flower Show at Garfield Park Conservatory , photo courtesy of the conservatory
During the 2021 winter break, enjoy the Serenity Winter Flower Show at Garfield Park Conservatory , photo courtesy of the conservatory

Chicago public schools are closed for the 2021-2022 school year winter break from December 20, 2021 to December 31, 2021, so there are at least two weeks of fun to be had with the kids. That's one way of looking at it ... the other way is "Oh my goodness, there are two whole weeks of days to fill with activities that keep kids occupied!" Luckily, we rounded up dozens of things to do in Chicago with kids during winter break, and they're all events and activities that keep kids active, engaged, and happy—not just busy. There are story hikes, Nights of Lights, holiday markets, winter activities, and loads of free activities for Chicago kids.

Keep an eye on our event calendar for fresh ideas every day. In case of emergency, break the glass and start working your way down this list of snowy day boredom busters.

Until January 3, parents: Stay strong. You can do this!

Sign up for our free newsletters to get local events and picks delivered straight to your inbox.

While we are trying to promote safer activities that occur outdoors or with social distancing guidelines in place, please keep your family and others safe by always wearing a mask and maintaining appropriate distance. If you arrive at an event that appears too crowded, try using the “nearby” search feature on our event calendar to find something else to do. 

Places featured in this article:


Trailside Museum of Natural History

The Morton Arboretum

Palos Heights Recreation Center

Enchanted Castle Restaurant & Entertainment Complex
Millennium Park Summer Music Series
Millennium Park, Jay Pritzker Pavilion - 6:30 PM Pick
Chicago Park District Movies in the Park
Multiple parks citywide - various times Pick
Arlington Heights Movie in the Park
Recreation Park - various times Pick
Free Days at the DuSable Museum of African American History
The DuSable Museum of African American Art - 10:00 AM
GO WITH THE FLOW, YOGA & BEER
Town Square - 7:00 PM
Neighborhood Guides
Activity Guides