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The 10 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

If you've ever spent the holidays in Chicago, you know that the city morphs into a magical winter wonderland as the year begins to wind down. With so many festive things to do and much cheer to spare, it's not hard to find things to do for Christmas in Chicago. Join in on the fun by getting a ticket to one of the season's top theater productions, sipping spiced wine at Christkindlmarket or admiring the dazzling holiday lights around town. Mix these 10 essential holiday activities 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

icon-location-pin McCormick Tribune Plaza & Ice Rink, Downtown

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, but if you don't own a pair of skates, you'll have to pay to rent some. 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. You can take advantage of free skating lessons on Fridays at 11am and Saturdays and Sunday at 9am. If it seems too warm to skate, call ahead—this rink is open through March 10, weather permitting.

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

icon-location-pin 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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