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The 14 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

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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

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Christkindlmarket
Photograph: Choose Chicago
Shopping, Markets and fairs

Christkindlmarket

icon-location-pin Daley Plaza, Loop
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You haven't experienced the holidays in Chicago until you've stepped into this giant open-air market inspired by a similar seasonal tradition in Nuremberg, Germany. At Christkindlmarket, guests can shop handcrafted items like nutcrackers, cuckoo clocks, beer steins and glass ornaments. When hunger strikes, nibble on potato pancakes, hot pretzels, schnitzel, döner and chocolate-covered treats. And no trip to Christkindlmarket is complete without a steaming mug of Glühwein, a traditional hot spiced wine (there's also hot cocoa for the kids).

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Photograph: Neal O'Bryan
Things to do, Late openings

ZooLights

icon-location-pin Lincoln Park Zoo | Chicago, IL, Lincoln Park
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Unless you've got a big budget, your Chirstmas light display won't hold an LED candle to the 2.5 million bulbs that festoon Lincoln Park Zoo during the annual ZooLights event. While most of the animals will be inside, guests are free to wander through the park, snap photos of the display and take part in a variety of activities throughout the holiday season. Ice sculpture carving, strolling carolers and Santa are regular fixtures of the event, but you'll also find ticketed happenings like a holiday market (Dec 3), an adults-only night (Dec 5), a live performance of music from A Charlie Brown Christmas (Dec 15) and a Zoo Year's Eve celebration (Dec 31).

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Caroling at Cloud Gate
Photograph: Peter J. Schulz
Things to do, Performances

Caroling at Cloud Gate

icon-location-pin Millennium Park | Chicago, IL, Millennium Park
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There's nothing stopping you from showing up in front of Cloud Gate (a.k.a. "The Bean") at any point during the year and belting out your favorite holiday songs, but you can do it with a crowd of like-minded exhibitionists at this annual series of winter concerts and sing-alongs. Meeting every Friday from November 29 through December 20, the caroling is lead by the likes of the Sounds Good! Choir (Nov 29), Mark Hubbard and The Voices (Dec 6), the Chicago Children’s Choir (Dec 13) and the Wicker Park Choral Singers (Dec 20). It's free to attend and it's just a short walk to the McCormick Tribune Ice Rink if you want to go for a quick skate after you sing.

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

Ice Skating in Millennium Park

icon-location-pin Millennium Park | Chicago, IL, Millennium Park
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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.

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Joffrey Ballet Nutcracker
Photograph: Cheryl Mann
Dance, Ballet

The Nutcracker

icon-location-pin Auditorium Theatre, Loop
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Having retired cofounder Robert Joffrey's production of The Nutcracker after nearly 30 years, the Joffrey Ballet debuted a brand-new version in 2016, set in Chicago against the backdrop of the 1893 World's Columbian Exposition. Featuring stunning new choreography by Christopher Wheeldon, the latest iteration of the classic Christmas will still have you humming “Dance of the Sugar Plum Fairy” for days after you leave the theater.

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Art Institute Lions wreath
Photograph: Grace DuVal
Things to do, Quirky events

Wreathing of the Lions

icon-location-pin Art Institute of Chicago | Chicago, IL, Grant Park
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On the day after Thanksgiving, the Art Institute's famous lions put on their holiday outfits as crews place wreaths around their necks. The Chicago Gay Men’s Chorus will lead a celebration on the museum's steps, complete with complimentary hot chocolate for anyone in attendance. After the ceremony, head into the museum to participate in family activities in the Ryan Learning Center or see “Andy Warhol — From A to B and Back Again.”

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Photograph: Liz Lauren
Theater, Drama

A Christmas Carol

icon-location-pin Goodman Theatre | Chicago, IL, Loop
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The Goodman Theatre’s annual holiday production of the Charles Dickens classic keeps its seasonal charm intact in its latest iteration. No bah humbugs here. Larry Yando returns for yet another outing as Ebenezer Scrooge, while director Henry Wishcamper guides the classic story of three spirits who confront Scrooge with the consequences of his miserly actions.

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Magnificent Mile Lights Festival
Photograph: Max Herman
Things to do, Festivals

Magnificent Mile Lights Festival

icon-location-pin Multiple venues
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Ring in the holiday shopping season at this two-day festival that takes place on Michigan Avenue. The fun begins on Friday, November 22, when Pioneer Court hosts family-friendly activities (including a visit from Santa Claus) and treats from Garrett Popcorn, Frango and Eli’s Cheesecake. On Saturday, November 23, stores on the Magnificent Mile will offer special experiences and offers throughout the day, before Michigan Avenue hosts a two-hour tree-lighting parade led by Grand Marshals Mickey Mouse and Minnie Mouse, which sets off from Oak Street at 5:30pm. Head to the Chicago River by 6:55pm to catch the spectacular fireworks display that closes out the evening.

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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.

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Illumination
Photograph: Courtesy Morton Arboretum
Things to do, Festivals

Illumination: Tree Lights at Morton Arboretum

icon-location-pin Morton Arboretum, Suburbs
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When the weather gets cold, the trees at Morton Arboretum light up in a sea of color at this popular winter event. Guests at Illumination walk down a one-mile path through the forest, admiring the magical display and seasonal music. Enjoy the display while strolling along a one-mile path and then warm up by a crackling fire with hot beverages and s’mores.

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Andrew Bird
Photograph: Amanda Demme
Music, Rock and indie

Andrew Bird

icon-location-pin Fourth Presbyterian Church of Chicago, Streeterville
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After taking a year off to complete his cheekily-titled album, My Finest Work Yet, whistlin' violinist Andrew Bird returns to the altar of the Fourth Presbyterian Church for a series of special performances. The winter "Gezelligheid" (a dutch word that roughly translates to "cozy") are something of a holiday tradition in Chicago, and offer a chance for fans to hear Bird play a solo set filled with new arrangements of classic tunes and collaborations with special guests. In the past, Bird has tested out new songs in front of a receptive audience and dabbled in expansive instrumental compositions that are piped through his array of horn speakers. Tickets for Bird's series of concerts at Fourth Presbyterian Church go on sale Friday, September 6 at 10am.

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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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The vintage facade of the Music Box makes it one of the best movie theaters in Chicago.
Photograph: Max Herman
Movies, Family and kids

Music Box Christmas Double Feature

icon-location-pin Music Box Theatre, Wrigleyville
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Ring in the holiday cheer with some classic, beloved Christmas films. Follow Jimmy Stewart’s path to redemption in It’s A Wonderful Life or sing along with Bing Crosby in White Christmas during the Music Box’s annual tribute to classic holiday cinema. Arrive early to meet Santa and belt out Christmas carols during the intermission, accompanied by the theater’s organist. You can snag tickets to one movie or both, depending on how much pure holiday cheer you can handle in the span of an afternoon.

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Chicago Helicopter Tour With Holiday Lights
Photograph: Courtesy Viator
Things to do, Walks and tours

Chicago Helicopter Tour With Holiday Lights

icon-location-pin Chicago Helicopter Experience, Bridgeport
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'Tis the season to experience the city lights on a very special holiday Chicago helicopter ride. Depart from the downtown Chicago heliport and be whisked over the magical skyline glowing in red, blue, and green. You'll soar 24 miles of Chicago gliding above the illuminated Willis Tower, Lincoln Park Zoo, Navy Pier, Wrigley Field, and so much more.The pilot-led flight is guaranteed to spread holiday cheer as you take in the one-of-a-kind nighttime views of the festive lights display below.

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