21 Fun Winter Break Activities in the Chicagoland Area

December 13, 2023

The kids are out of school for two weeks, it’s cold, and you need to wear them out so bedtime is quick?! I’ve got some great winter break ideas for you! I’ve divided up these ideas into two categories: Budget-Friendly and Splurge (meaning more than about $30 per person.) I hope this helps you plan out your “break!”

Budget-Friendly Activities in Chicago for Kids

  • Have lunch at Butch McGuires! This uber-festive pub on Division goes ALL out with the decorations. My kids love watching the model train and chowing down on tots. They don’t take reservations, so go as early as you can!
  • Altitude Indoor Trampoline Park – My kids love the huge trampolines and they always sleep so well that night!
  • Chicago History Museum – They have a kids’ exhibit about the Great Fire for those under age 12, and it’s super interactive. Illinois residents under the age of 18 are always free. You could also pair this with the zoo since it’s across the street! Or grab a pizza from Ranalli’s on Clark.
  • Downtown Holiday Tree Hop – There are so many beautiful Christmas trees on Michigan Avenue!
  • Cuddle Bunny – book an appointment at this cute Lincoln Park studio and literally cuddle bunnies for an hour. Head down the street to 2D Restaurant afterward for lunch or Stan’s Donuts for a snack.
  • Exploritorium – This indoor play space in Skokie has activity stations like a big water table area, pretend play, a multi-level soft play structure, and a sectioned-off area for crawlers and toddlers. Bonus points for the big parking lot, too! Best for kids ten years and under.
  • Fit City Kids – Another great indoor play space with a huge soft play structure. Check out their camps and classes, too! They are actually running winter break camps, too!
  • Funtopia – Funtopia in Glenview specializes in rock climbing and rope courses but also has a big multiplay area for the kids who feel safer on the ground. 🙂
  • The Winter Flower Show at Garfield Park Conservatory – This free (reservation required) event at the Garfield Park Conservatory is always so beautiful and fun! This year’s theme is Celebrating Silver and a great winter break easy activity to do.
  • Ice Skating – There are a bunch of different options! McCormick Tribune Ice Rink in Millennium Park, the Maggie Daley skating ribbon, Midway Plaisance Ice Rink in Hyde Park, or Parkway Bank Park in Rosemont.
  • Spend a day in Pilsen – visit the National Museum of Mexican Art, play at Harrison Park, have dinner at 5 Rabanitos or Rubi’s, shop on 18th St, and then see a drive-in holiday movie at ChiTown Movies.
  • Whirlyball – Whirlyball is so much fun, and it’s not just whirlyball – they also have bowling and laser tag! Must be a minimum of 54 inches tall to play whirlyball and seven years old for laser tag.
  • ZooLights at Lincoln Park Zoo: This is the quintessential Chicago holiday light experience! ZooLights is either free or $5, depending on what night you go.

More Fun Ideas for Chicago Kid’s Activities (Worth the Splurge!)

  • The Museum of Science and Industry – MSI’s annual Christmas Around the World and Holidays of Light exhibitions are always awe-inspiring!
  • Chicago Children’s Museum at Navy Pier – This kid’s museum is HUGE and amazing. Prepare to be there all day or to make promises to come back! Be sure to check their winter hours.
  • Color Factory – my kids LOVE Color Factory! It has interactive displays, surprises, and an epic ball pit. It’s at the bottom of the Willis Tower and there’s plenty of dining in the building and nearby.
  • DuPage Children’s Museum – This Naperville institution has tons of activities that focus on science, math, and art.
  • Harry Potter: Magic At Play – Immersive exhibits are all the rage, and Harry Potter: Magic At Play is the newest to open in Chicago. I got a sneak peek, and I highly recommend it! Yes, it’s a splurge. Maybe for a special occasion? Here’s my review! The exhibit is located in Water Tower Place and here for a limited time! Get more info and tickets here.
  • LEGOLAND Discovery Center – For your newest LEGO lover or your oldest, LEGOLAND is the ultimate brick destination. I love the displays and the kids love all the building opportunities, rides, and 4D movies.
  • Puttshack in Oakbrook Center – We spent the day here last holiday season and had so much fun! Everything is automated from your golf ball, all the various courses are tech-infused, they have kid-size clubs, and yummy food and drinks. Reservations are necessary.
  • Winterland at Gallagher Way – this is our new favorite tradition! The kids loved the holiday train, ice bumper cars, ice skating, and the frozen slides. Tickets are $5, but attractions are purchased separately, and unless you’re traveling via train/bus to Wrigleyville, you’re going to need to pay for parking.
  • Jack Frost Holiday Pop-up – their new location is smaller but better! The kids will love ice skating, all the lights, and the winter bumper cars!

Did this give you some ideas to fill those chilly days during your kid’s winter break? I’m actually feeling more excited now that I have a plan. 🙂 Let me know what you decide to do! If you want to get out of town, check out my favorite Winter Midwest Getaways here!



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