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The 16 best things to do during the holidays in Chicago

Experience the holidays in Chicago with festive theater productions, steaming beverages and a giant German market

Photograph: Neal O'Bryan

As the year begins to wind down, the city morphs into a magical winter wonderland, thanks to a slew of amazing Chicago Christmas events. If you don't mind braving the cold, check out sparkly Christmas lights in Chicago, take a lap around an ice-skating rink or sing carols next to the Bean. Of course, no winter is complete without a trip to Christkindlmarket Chicago, which sets up outposts in the Loop and Wrigleyville this year. If you'd rather be warm and cozy, snag theater tickets to see beloved annual productions like The Nutcracker and A Christmas Carol. Mix in these essential Chicago Christmas events with your own seasonal traditions for a winter you won't soon forget. 

RECOMMENDED: Our complete guide to Christmas in Chicago

Things to do during Christmastime

Photograph: Patrick L. Pyszka
Things to do, Ice skating

Ice Skating in Millennium Park

Millennium Park | Chicago, IL, Millennium Park

Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Admission to the rink is free, and you can rent skates for $13–$15. The most popular time to hit the rink is in the evening, so show up earlier if you don't feel like waiting in line for your chance to slide around. Take advantage of free skating lessons on Fridays at 11am and Saturdays and Sundays at 9am. If it seems too warm to skate, call ahead—this rink is open through March 8, weather permitting.

CTA Holiday Train
Photograph: Grace DuVal
News, Transport & Travel

CTA Holiday Train

Want to ride the rails with Santa? The CTA's Holiday Train brings cars packed with lights, ribbons and holiday cheer to every single train line in the city from November 29 through December 23. If you're lucky, you'll spot the train and snap a photo, but if you're really fortunate, you might score a seat on the most festive mode of public transportation. Check out the CTA's website for a complete Holiday Train schedule and don't forget to wave at Santa if you see it zooming by.

The Great Tree in Macy's Walnut Room

The Great Tree at Macy's Walnut Room

You'll have to wait quite a while to get a table next to the tree in the Walnut Room, the seventh-floor restaurant inside Macy's (formerly known as Marshall Fields). But the 45-foot-tall tree, which sparkles with 3,000 ornaments and 6,000 LED lights, can be viewed from outside the restaurant, which means that you won't have to splurge for a chicken pot pie simply to experience one of the most spectacular holiday displays in the city.

Photograph: Martha Williams
Bars, Dive bars

Glögg at Simon’s Tavern


Look for the glowing neon fish sign hanging over this classic Andersonville dive, where locals and visitors have been pumping quarters into the jukebox for more than 80 years. When the holiday season arrives, you'll want to order the bar's cold-weather specialty: a warm mug of a Swedish variation of spiced wine called glögg, served with an authentic ginger pepparkakor cookie.