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Things to do in or around Chicago during the holiday season!
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items My family loves spending time in Chicago for the holiday season. I have put a list together for you to enjoy as the season approaches. We love everything Chicago has to offer during the holidays. I hope you do to!
Christkindle Market is filled with many ornaments and gifts. Take home a tiny hot chocolate cup to add to your collection.
Christkindlmarket Chicago November 21- December 24, 2025
A family favorite to start our holiday season, watching the light parade down Michigan Avenue. See your friends Mickey, Minnie and Santa! Fun for the whole family!
Magnificent mile light festival November 22, 2025 @ 5:30pm
Enjoy a beautiful night ice skating in Maggie Daley Park, the most fun we've ever had as a family. Make sure to make reservations, they do sell out fast!
Maggie Daley Park Ice Skating Ribbon November 14, 2025 Opening Day!
Make sure to check out the Christmas tree in Millenium Park! So many beautiful lights shining on the tree.
City of Chicago Christmas Tree November 21, 2025
The perfect setting to indulge in festive cocktails, seasonal bites and breathtaking views of the city. Make sure to book reservations before going.
Visit Our Chicago Rooftop Bar - Drinks & Dining With A View
Enjoy rides, ice skating, festive decor fun for the entire family!
Winter WonderFest December 5- January 4, 2026
An enchanting 1.3 mile trail of twinkling lights and showstopping displays. Bundle up, and sip on hot chocolate as you view these incredible lights.
Chicago Botanic Garden Lightscape November 14- January 4, 2026
More than 3.5 million lights, and interactive displays transform the Zoo into a winter wonderland.
Brookfield Zoo Chicago - Holiday Magic
More than 3 million lights, displays and festive experiences that capture the magic of the season. Mondays are free with the exception of December 22!
ZooLights Presented by Invesco QQQ and ComEd Lincoln Park Zoo
What a fun night out to enjoy the season with your closest friends or family. Ice Skating, Pop up shops, Axe throwing, cocktails and bumper cars. The season begins November 15, 2025
Jack Frost Christmas Pop Up Fulton Market
It wouldn't be Christmas without seeing The Nutcracker Ballet. Fun for the entire family.
The Nutcracker
My family got to experience one of the Metra Christmas trains after a day in the city, last year. It did not disappoint, and was probably one of our favorite things to have talked about.
Metra to run Holiday Trains on six lines
Want to enjoy the views of the amazing Christmas lights, try Chicago 360! Make sure to make reservations. It does get busy especially on the weekend!
360 CHICAGO
Another fun thing to do no matter what the season is visiting Willis Tower's Skydeck. If you're brave try the tilt. Enjoy so many views Chicago has to offer.
The Skydeck Chicago
A fun mall to visit especially after spending all day outside in the cold. They have a lot of stores and places to eat or just relax.
Water Tower Place