Winter in Chicago: 10 Activities Families will Love

Posted By Katie on Sep 29, 2015

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Winter in Chicago is freezing cold. But the magic of this beautiful city comes alive during the holidays, and with world-class museums and a beautiful city skyline, Chicago is a wonderful big-city destination, even in the winter.

I lived in Chicago when my two oldest daughters were preschoolers, and I fell in love with this family-friendly city. Chicago is safe and easy to navigate in a car or via public transportation.

Here are 10 activities for families that will make you love winter in Chicago. If you think you have time for a several of them, I recommend checking out a Chicago CityPASS.

Winter in Chicago: 10 activities that families will love |

Get Lost in a Maze of Mirrors

The newest addition to Chicago’s Museum of Science and Industry is a maze of mirrors that will have everyone in your family cracking up as you try to find your way around. Once you master the maze, enjoy the hands-on science activities throughout the museum. Take a tour deep into a coal mine, or walk through a U-505 submarine. I cannot rave enough about how much I love this museum, and as an added bonus, the holiday decorations feature beautiful trees from around the world if you visit in November or December.Winter in Chicago with Kids: 10 Activities Families will Love |

Step off the Ledge at the Skydeck

Visit the Skydeck of the Willis Tower for a memorable experience stepping out onto the four-foot glass ledge from the top of the tallest building in America. Take an elevator ride up to the 103rd story and learn some Chicago history in the small museum up top as you take in stunning views of the big city and frozen Lake Michigan.

Play with Butterflies

Winter blues disappear when you step into the 2,700 square foot butterfly greenhouse at the Peggy Notebaert Nature Museum. Home to over 75 species of butterflies, this tropical paradise is a great place to escape from winter in Chicago. This nature museum is smaller than some of the huge museums in Chicago, but no less impressive. The hands-on exhibits are interesting and fun for kids and parents alike.

Experience the Blue Man Group

When your legs get tired from exploring Chicago’s spectacular museums, go see the Blue Man Group perform. This fun show is a mix of music, comedy, and visual arts, and families of all ages enjoy the interactive show.

Disclosures: Children under 3 are not permitted in the Blue Man Group theater, and there will be strobe lights and loud percussion during the show, so take the sensitivities of your younger children into consideration before you splurge on tickets to the show. The show runs about one hour 45 minutes with no intermission.Winter in Chicago with Kids: 10 Activities Families will Love |

Ice Skate on the Outdoor Rink at Millenium Park

Chicago’s beautiful Millenium Park is a delight in the summer, but the free ice skating on the McCormick Tribune Ice Rink in the park is a great way to get rosy cheeks and some fresh air. Yes, I did say free ice skating, however skate rentals are $12. Grab hot chocolate or snacks at the nearby Park Grill Cafe.

Take the Pizza Challenge

Chicago is famous for its deep-dish pizza, so why not make it a family challenge to find the best deep-dish pizza in the city? When my family took the pizza challenge, we had a great time stuffing ourselves on delicious slices and analyzing every bite. Some of the best family memories can be made while laughing over dinner.Winter in Chicago With Kids: 10 Activities for Families |

Go Ape in the Treetop Canopy at Lincoln Park Zoo

Lincoln Park Zoo is a FREE zoo that families can enjoy year-round. In the cold winter months, visit the indoor exhibits and let the kids go wild in the treetop canopy climbing adventure, a new innovative indoor playground. If you visit in near the holidays, consider an evening trip to Lincoln Park Zoo to enjoy Zoolights and a visit with Santa.

Visit a World-Class Museum

Chicago’s museums are some of the best I’ve ever visited. Visit the Field Museum to see Sue the T-Rex, or teach your kids about impressionism at the Art Institute of Chicago. Check out the Shedd Aquarium and the Adler Planetarium for the science enthusiasts in your family. Younger children will love playing at the Chicago Children’s Museum on Navy Pier. Whichever museums you choose, you will wish you had more time to explore.

Winter in Chicago With Kids: 10 Activities for Families |

“American Gothic” at the Art Institute of Chicago.

Shop on the Magnificient Mile

Make all their dreams come true with a stop at the American Girl store or the Lego store. Little ladies love shopping at the American Girl store or stopping for afternoon tea or a meal. The Lego creations at the Lego store are worth stopping for even if you do not plan to buy Legos. We love Dylan’s Candy Bar, which has a two-story candy display. My favorites thing at Dylan’s? Introducing my kids to the nostalgia candy that I bought as a kid. Remember Fruit Stripe gum or Big Hunk candy bars? You can find them at Dylan’s Candy Bar.

See the Holiday Window Displays

If you are in Chicago during the holidays, do not miss the holiday window displays at Macy’s on State. This Chicago tradition has been going on for decades. When you get cold, head inside to see the beautifully decorated Great Tree in the Walnut room and perhaps stay for a bite to eat and some shopping.

This next one is a bonus because it is not technically in Chicago, but it’s worth knowing about if you are movie-lover visiting Chicago.

Drive by the “Home Alone” House

This outing will require a car and is about 50 minutes north of downtown Chicago, but if your family has fallen in love with the “Home Alone” movies, it is a fun detour to the upscale neighborhood of Winnetka to drive by the home featured in “Home Alone.” You can find it at 671 Lincoln Ave., Winnetka, IL.

Winter in Chicago With Kids: 10 Activities for Families |

My son, the Macaulay Culkin look-alike.

Should you buy a Chicago CityPASS?

If you have a few days in Chicago and want to visit several of these destinations, consider a Chicago CityPASS to save money on admission. In the winter when you anticipate spending time indoors, I recommend a Chicago CityPASS.

Disclosure: The CityPASS link is an affiliate link.

Planning a trip to Chicago?

Looking for more fun things to do in Chicago?  Check out our Illinois page.

Katie is a busy mom living in Northern Virginia with her husband and five children ranging in age from toddlers to teens. When she isn't traveling, she is planning her next trip. Katie loves all types of travel, but she especially loves beach vacations. The Outer Banks of North Carolina is a favorite family destination.


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