Holiday by Jason Mrozik
Classic Chicago Holiday Traditions That Never Get Old
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There’s something truly special about the holidays in Chicago—a blend of big-city sparkle and neighborhood charm that makes you want to grab a hot cocoa and soak it all in.
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Whether you're a lifelong local like me or spending your first season in your new home, here are a few timeless traditions that define what it means to celebrate the holidays in the Windy City.
Ice Skating Under the Skyline... and at Wrigley
You haven’t done winter in Chicago until you’ve laced up your skates. Some of the best rinks:
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Maggie Daley Skating Ribbon – A winding, scenic loop surrounded by skyscrapers.
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McCormick Tribune Rink (Millennium Park) – Right under The Bean, with festive tunes playing. (Pro tip: usually a shorter line than Maggie Daley!)
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Gallagher Way Rink (Wrigleyville) – Skate outside Wrigley Field for major holiday movie vibes.
Skate rentals are available at all locations. Whether you’re graceful or just trying not to fall, it’s all about the experience.
Christkindlmarket – Downtown & Wrigleyville
Modeled after Germany’s traditional holiday markets, Christkindlmarket has been a Chicago staple since 1996.
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Daley Plaza (Loop) – Handmade ornaments, mulled wine in those iconic mugs, roasted nuts, and twinkle lights everywhere.
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Gallagher Way (Wrigleyville) – A smaller, more relaxed version with local vendors and cozy food stands—plus fewer crowds.
Both markets bring serious holiday charm. Just pick your vibe.
Sledding, Tobogganing... and Yes, Skitching
The CTA Holiday Train
The CTA Holiday Train is pure magic on rails. Santa waves from a sleigh between the cars, elves greet riders inside, and every inch of the train is covered in twinkle lights.
Track it online—it’s worth adjusting your commute just to catch a glimpse.
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One of my favorite parts of being a Realtor in this city is helping people put down roots—because once you call Chicago home, these traditions start to feel like your own.
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Whether you're cozy in a Bucktown condo or hosting your first holiday dinner in North Center, I hope these classic traditions bring a little extra magic to your season.
When the snow hits, it’s time to find a hill:
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Warren Park (West Ridge) – A beloved favorite.
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Mount Trashmore (Evanston) – A legendary repurposed landfill with great elevation.
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Horner Park & Palmisano Park – Smaller but fun sledding spots closer to the city center.
And for the true Chicago kids… who remembers skitching? (Grabbing a car bumper and gliding on boots down icy streets—definitely not safe, but totally unforgettable.)