Things to Do with Chicago Kids During Winter Break

Plan out your winter break with these fun things to do for kids!

A two-week break from school can still be a bit overwhelming — for kiddos and grown ups! Luckily, there are plenty of things to do at home or around town to help cure your kids’ boredom. 

Winter Break Bucket List

Add fun this winter break with some of these adventuresome and unique opportunities that can only be done right here in Chicago.

Drink hot chocolate.

Stay warm during break with some tasty hot chocolate. Whether you’re making the drink at home or buying already-made hot cocoa in Chicago, your kids won’t forget to add lots of whipped cream and marshmallows. Also, try out the latest food trend – hot chocolate bombs!

Celebrate the holidays.

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. 

Go ice skating.

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.

Cruise down sledding hills.

Families looking for some outdoor thrills can go sledding at one of these local sledding hills around the city and suburbs. Bundle up, then enjoy these steep slopes or hills with great views. 

Bake some cookies.

Whether you’re making cookies for Santa or want to enjoy something sweet with the family, these holiday cookies won’t disappoint.

See a movie.

If you can’t make it to a movie theater, there are still plenty of new family movies and shows streaming this month.

Connect with long-distance relatives.

While we will miss seeing some family members this holiday season, you can still connect with them virtually. Here are some fun family games to try over video chat.

Take a photo with Santa.

Santa Claus is coming to town! These Santa experiences will make your kids so happy (and fingers crossed they take a great photo with Santa).

Volunteer as a family.

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.

Read a seasonal book. 

What better time to curl up with a book than over winter break? If your child needs a book recommendation or you’re looking for a new title to read together, check out these holiday books for kids, or pick up a winter-themed children’s book

Shop local.

Speaking of volunteer, why not donate a toy for a child in need? Head to local stores to find these toys featured in our Holiday Gift Guide.

Indulge in a special holiday treat.

Winter break is the sweetest time to indulge your child’s sweet tooth! ‘Tis the season for peppermint treats, sugar cookies, gingerbread-flavored everything and so many more sugar plum treats. Enjoy one of these festive treats, from Christmas donuts and winter coffee flights to over-the-top hot chocolates and shakes.

Watch this, do that.

Rewatch some of your favorite family films like “Toy Story” or “Moana“. Our Watch This, Do That series pairs some great lessons and activities with these great films.

Count down to 2024.

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. 

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