Chicagolandโ€™s Coolest Winter Break Adventures for Kids of All Ages

Keep the family entertained this winter break with Chicagolandโ€™s best activitiesโ€”from ice skating to holiday lights, hot chocolate and more!

Winter break offers two weeks of excitement and family fun, but keeping kids entertained can be a challenge! Thankfully, Chicagoland is filled with unique winter break activities for kids and families.

Whether youโ€™re looking for indoor adventures or outdoor excitement, there are plenty of things to do in Chicagoland this winter break to keep boredom at bay. Check out these top family-friendly activities and create unforgettable memories right here in the city and suburbs.

This story was updated on Nov. 13, 2024 by Chicago Parent’s Audience Development Manager, Katina Beniaris. Her work included adding her favorite winter break activities for Chicagoland. Questions? Email katina@chicagoparent.com.

Best Winter Break activities for Chicagoland kids

Visit a hot chocolate spot

Le Chocolat du Bouchard
Photo credit: Le Chocolat du Bouchard

Warm up this winter break by visiting one of Chicagoโ€™s best hot chocolate spots! From classic cocoa to extravagant, over-the-top creations, these local cafes offer something special for every taste.

Feel festive at a holiday attraction

german-christmas-market
Photo Credit: Christkindlmarket

It’s the holiday season, and there’s so much you can pack into winter break! Check out our holiday family guide filled with places to see lights, in-person attractions and more festivities.ย 

Go ice skating at an outdoor rink

best things to do with chicago kids in winter
Photo credit: Choose Chicago

The weather outside might get frightful, but you must admit that there are some winter activities that you absolutely love! Lace up your skates and take a spin around these outdoor skating rinks.

Explore a museum

Thomas and friends exhibit
Photo credit: Minnesota Children’s Museum

Discover something new as a family by visiting one of Chicagolandโ€™s many museums! Plus, winter break is your last chance to see Kohl Children’s Museum’s Thomas & Friends: Explore the Rails! and Christmas Around the World and Holidays of Light at Griffin Museum of Science and Industry before they leave on Jan. 5.ย 

Give back together as a family

Volunteering

Photo Credit:ย Little Brothers Friends of the Elderly

Set some time aside during winter break to give back as a family. Here are some ways to give back as local non-profit organizations this season.

Count down to 2025

Bubble Bash
Photo credit: DuPage Children’s Museum

Celebrate the new year with these exciting kid-friendly New Year’s Eve parties that you can attend before you head home to count in the new year as a family.ย 


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Katina Beniaris
Katina Beniaris
As audience development manager, Katina Beniaris digs into data to help the Chicago Parent team learn about our audiences and tailor better content for them. She has more than five years of experience in content creation.
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