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15 Things to Do in Chicago this December 2025

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Looking for what to do in Chicago this December? This list brings together 15 top events, activities, and festive experiences happening around the city. Perfect for planning holiday outings, date nights, and fun winter adventures.❄️🎄🎅🏻🎉
 
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You can Ice Skate, watch a free Ice show and have a great time while savoring the Christmas spirit!
Jack Frost Holiday Pop-Up
 
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A great way to feel the Christmas spririt around Chicago.
Winterland at Gallagher Way
 
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I you like Opera and musical shows that turns around Christmas and End of Year, this might be a good idea
The Nutcracker | Joffrey Ballet
 
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The admission is completely free but there’s a long line to get in there. There hot chocolates are bomb! Plus you can get a cute Christmas mug to go when you buy it!
Christkindlmarket Chicago
 
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If you don’t like to be outside in the cold, this will be a great place to go. This is an indoor Christmas theme attraction. They even have an indoor Ferris wheel 🤩
Winter WonderFest
 
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The biggest conservatory containing a variety of plants and flowers, is hosting an event that turns around winter flowers.
Garfield Park Conservatory
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The trees are decorated in a beautiful Christmas theme lighting. It is beautiful to take pictures and have wonderful souvenirs!
Chicago Botanic Garden Lightscape
 
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If you’d like to see how a Zoo would be decorated for Christmas, you should check this out!
Lincoln Park Zoo
 
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Outdoor Ice Skating Rink at the middle of Downtown!
McCormick Tribune Ice Rink
 
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It has the biggest and tallest Sapin tree I’ve ever seen! Going from the first to the 21st floor! It’s beautiful!
The Walnut Room
 
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Walk by the lake and look at the beautiful decorations to celebrate the end of the year. Their attractions in the theme of Christmas are top tier.
Navy Pier
 
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If there’s one thing I like about Chicago, it’s that you’re going to ride the train with Santa on December! This is an on schedule event and will not happen throughout the month!
Allstate CTA Holiday Train & Bus - Chicago
 
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The tallest building at Chicago will be transformed into a Christmas diving experience.
Skydeck Chicago
 
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It’s beautiful! You get to see how Christmas is celebrated around the world! With different types of Sapin tree decorations.
Christmas Around the World and Holidays of Light
 
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Fannie May's Jolly Trolley will be driving around Chicago this holiday season from Dec. 5-21 decked out with twinkling lights, garlands and festive ornaments. The Jolly Trolley is free to ride! Taste Conductors guide you to four different Chocolat...
The Fannie May Jolly Trolley Tickets, Multiple Dates
 
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If you’re a Marvel’s fan, Chicago’s hosting a Spider Man exhibition for free!
Spider-Man: Beyond Amazing – The Exhibition in Chicago