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Photograph: Neal O'Bryan

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

By Zach Long

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

CTA Holiday Train
Photograph: Grace DuVal

1. CTA Holiday Train

News Transport & Travel

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

2. 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

3. Glögg at Simon’s Tavern

Bars Dive bars Andersonville

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.


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