Family fun in the Midwest is all about embracing the seasons. In the winter, that means welcoming the snow, but also knowing when to get out of the house for indoor fun that lets kids stretch their legs (or bounce off energy).
We’ve rounded up winter activities for keeping the memories warm even as the weather drops and the nights grow long. Here, you’ll find the best sledding hills, new tubing adventures, outdoor ice rinks for breaking out the skates… as well as spots for bowling, bouncing, and other indoor fun.
We hope it inspires your family to bundle up and spend some quality time together this winter.
This guide is sponsored by Chicago Wolves, whose season runs all winter long!
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Outdoor Winter Adventures
Bundle up and head outside!
From zipping down sled hills to gliding across the ice, these activities will help your family embrace the magic of winter. Find local spots for sledding, tubing, skiing, snowboarding, ice skating, and even peaceful snowshoeing and hiking trails.
Winter Holidays & Celebrations
Mark your calendars!
Whether you’re planning winter break, celebrating the holidays, or looking for meaningful ways to spend MLK Day and Valentine’s season, this section is packed with special events and fun things to do with kids during the colder months.
Cozy Food & Dining
Warm up with food that’s fun!
These unique places to eat turn a simple meal into a family adventure — from dining inside a glowing igloo dome to sipping over-the-top milkshakes or taking advantage of kids-eat-free deals all winter long.
Active Indoor Play
Get moving, no snow gear required!
Need to burn off energy when it’s too cold to play outside? These indoor spots offer roller skating, climbing, bouncing, and more — all perfect for getting the wiggles out.
Indoor Games & Challenges
Challenge each other to something new!
Arcades, bowling, escape rooms, and laser tag are great ways to have a blast indoors while making family memories. These are all kid‑friendly and filled with interactive fun.
Indoor Escapes & Entertainment
Take the fun inside with splashes, shows, and staycations.
Stay cozy indoors this winter with live theater performances, indoor swimming fun, and even a family-friendly hotel getaway. No passport required!
Winter Activities at Home
Don’t forget about adding at-home activities to your winter bucket list! Build a snowman with this adorable kit, have a snowball fight, make an igloo, bake cookies together (this is our favorite cookie recipe lately), snuggle up and watch a movie together (check out this list of 50 movies all kids should watch before they are 12 from Common Sense Media!), try a new soup recipe, or sit by the fire and play a game.
