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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: Choose Chicago
Shopping, Markets and fairs


Daley Plaza, Loop

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).

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


Lincoln Park Zoo | Chicago, IL, Lincoln Park

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).

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

Caroling at Cloud Gate

Millennium Park | Chicago, IL, Millennium Park

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.

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.

Joffrey Ballet Nutcracker
Photograph: Cheryl Mann
Dance, Ballet

The Nutcracker

Auditorium Theatre, Loop

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.

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.

Photograph: Liz Lauren
Theater, Drama

A Christmas Carol

Goodman Theatre | Chicago, IL, Loop

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.

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: Courtesy Morton Arboretum
Things to do, Festivals

Illumination: Tree Lights at Morton Arboretum

Morton Arboretum, Suburbs

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.

Chicago Botanic Garden, Lightscape
Photograph: Chicago Botanic Garden
Things to do, Exhibitions


Chicago Botanic Garden | Glencoe, IL, Suburbs

The Chicago Botanic Garden hosts a new display of festive lights, giving guests a host of shimmering reasons to visit the forest preserve during the holiday season. Set along a one-mile path, the after-dark experience features a series of installations to explore, including the a 110-foot tunnel made up of 100,000 lights and a group of trees festooned in blubs that "sing" holiday songs. 

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.

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

Music Box Theatre, Wrigleyville

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.

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

Chicago Helicopter Tour With Holiday Lights

Chicago Helicopter Experience, Bridgeport

'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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