14 Winter Break Activities to Try in Chicagoland

With families spending more time at home this year, a two-week break from school can still be a bit overwhelming. There are still a few things to do at home or around town to help cure your kids’ boredom. Add fun this winter break with some of these adventuresome and unique opportunities that can only be done right here in Chicago.


Note: We’re updating our website as quickly as we can, but changes may occur due to COVID-19. Please double check before heading out for the most updated information on safety precautions and any last-minute cancellations. Stay safe!


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 plenty of things to do safely at home.


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.


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. Plus, join us for our Virtual Cookie Swap to share your own recipes.


Participate in a scavenger hunt.


If you love seeing holiday lights, pack up your car to head to your favorite local attractions or see some neighborhood displays. You can bring along our Holiday Scavenger Hunt download to make it an unforgettable outing for the whole family.


See a movie.


Movie theaters may be closed, but there are still plenty of new family movies and shows streaming this month. If you want to get out of the house, go see a holiday movie at one of these local drive-ins.


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). We even included some virtual options for families, too.


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.


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 2020 Holiday Gift Guide.


Be a tourist (virtually).


While museums and some other attractions are closed, your family can still “visit” from home thanks to these virtual experiences.


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. We have even included some new ones such as Over the Moon and Jingle Jangle: A Christmas Journey.


Dine outdoors.


If you are tired of ordering takeout, take a break and enjoy a meal at these local restaurants offering outdoor dining options this winter. Or you can pick up a sweet treat to enjoy at home.


Count down to 2020.


Celebrate 2020 with these exciting kid-friendly New Year’s Eve parties that you can enjoy virtually.


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