Chicago’s Ultimate Holiday Guide

The holidays are upon us!

You know what that means – events, events, and more events. But how could you possibly know everything that’s happening? Where do you even start? There’s only so much one person can take in.

That’s where Chicago’s Ultimate Holiday Guide comes in. Our little UrbanMatter elves have wandered around the city in search of the best holiday events around Chicago. Here’s what they had to report.


Winter Wonderfest
Photo Credit: Winter Wonderfest Facebook

Winter WonderFest at Navy Pier
November 30 – January 6
Navy Pier

With over 24 rides in a 170,000 square-foot space, Winter WonderFest is a children’s paradise. Inflatable slides, tubing hills, and obstacle courses give this jam-packed event an unparalleled indoor winter experience. Check out the indoor Ferris wheel and Blackhawks Ice Skating rink.


Christkindlmarket Chicago
Photo Credit: Christkindlmarket Facebook

Christkindlmarket Chicago
November 16 – December 24
Daley Plaza

The boot-shaped mugs are back, and so is Chicago’s 23rd annual open-air Christmas market. Enjoy traditional German cuisine, crafted holiday items, and all the holiday fanfare you can handle. The market itself is free, but the goods are gonna cost ya. Oh, and you NEED to try the hot, spiced wine. Just trust us on that one.


Lincoln Park ZooLights Festival
Photo Credit: ZooLights

ZooLights at Lincoln Park Zoo
November 23 – January 6
Lincoln Park Zoo

It wouldn’t be too much of a stretch to call ZooLights Chicago’s most captivating light show. If 2 million lights brightening every inch of the zoo wasn’t reason enough to visit – you’ll also have access to ice skating, visits with Santa, and of course, animals. The hype is real, folks.


Wicker Park Ice Skating

Ice Skating
Times Vary
Locations Around the City

You can’t make a holiday guide without ice skating. Pick a place: Millennium Park, Maggie Daley Park, Lincoln Park Zoo, Wicker Park – the list goes on and on. The Chicago Park district has 11 different rinks to choose from (and one of them is indoors).


Macy's Christmas Windows
Photo Credit: Tyler LaRiviere

Christmas Windows
November 3 – January 6
Macy’s on State 

Macy’s holiday window decorating began in 1897, making it a timeless annual tradition. This year’s theme, Reason to Believe, honors Chicago landmarks in various assortments and gives you more reasons than one to bask in the holiday season. 


Christmas Around the World @ the Museum of Science and Industry, Chicago
Photo Credit: MSI

Christmas Around the World at the Museum of Science and Industry
November 15 – January 6
Museum of Science and Industry

The annual Christmas Around the World exhibit at the Museum of Science and Industry is here, and it’s a sight to see. 50 trees, decorated from nations around the world, saturate the museum’s popular exhibit. In the middle, the Grand Tree, a towering, 45-foot goliath decorated by 30,000 lights and hundreds of vividly glowing ornaments.


CTA Holiday Train
Photo Credit: Chicago Transit Authority

The CTA Holiday Train
November 23 – December 21
Various CTA Lines

Santa’s taking a short vacation from the North Pole before Christmas time. His home for the next month? The CTA Holiday Train. Take your commute to the next level when you ride this festive train, which comes equipped with lights, reindeer, garland, decorations, candy, and of course, Santa’s loyal team of elves (that jolly old soul isn’t going to travel by himself, ya know).


10 Things to Do in Chicago This Winter

10 Things to Do in Chicago This Winter
Chicago (duh)

Is this guide based off the holidays? Well…no. But hey, why not add in some bonus info on winter as a whole? This cold season goes well beyond December, as we begrudgingly know all too well. 


Have anything to add to Chicago’s Ultimate Holiday Guide? Let us know!



Featured Image Credit: Christkindlmarket Facebook

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