City Guide / Chicago

12 Things to Do in Chicago During the Holidays

By Kailey Hansen | Dec 8, 2021

If you’ve ever spent a winter in Chicago, you know there is no place like this city during the holidays. Yes, the cold temperatures require a little extra bundling during December, but it’s also one of the best times to experience festive traditions and fun activities.

From catching the annual Macy’s window displays on State Street to grabbing a Christmas ale at a holiday pop-up bar, Chicago is the ultimate city to experience the most wonderful time of the year.

Here are 12 things you won’t want to miss while living in Chicago during the holidays:

1. Visit the Christkindlmarket

Without a visit to Chicago’s beloved seasonal German market, the holidays just aren’t done right. This year, there are two locations: the original market on Daley Plaza in Downtown Chicago, and the smaller but just as magical secondary location in Wrigleyville. The Christkindlmarket prides itself on being Chicago’s “most authentic traditional holiday market outside of Europe,” hosting tons of local vendors who sell goods ranging from mulled wine and Bavarian pretzels to handmade ornaments.

This place is a haven for holiday shopping if you want to give your loved one something special. Grab them the annual Christkindlmarket mug, or visit a booth selling scarves and hats, woodwork home decor, or a delicious bag of roasted nuts. Here, you can experience more than just browsing seasonal trinkets—the market is a melting pot of European culture, with a variety of winter traditions represented, including Saint Nicholas himself and the menacing mythical being Krampus. 

2. Sing along to “White Christmas” at the Music Box Theatre

The Music Box Theatre, nestled in the charming northside neighborhood of Lakeview, is an ornate building originally constructed in 1929. These days, it’s a local treasure and offers screenings of both new releases and old movies. Perhaps its most notable tradition is its “Music Box Christmas Sing-Along and Double Feature” each December, which first shows Irving Berlin’s “White Christmas” (the sing-along version, as promised) followed by “It’s A Wonderful Life.”

This double feature has plenty of showings throughout the winter season, but tickets sell fast. If you love a bit of sentimental nostalgia during the holidays, this wholesome celebration of old-school Hollywood Christmas is right up your alley. Bundle up, hop on the Brown Line train to the Southport stop, and let yourself experience true holiday magic at this historic Chicago landmark.

3. Drink and be merry at Chicago’s holiday pop-up bars

Ring in winter with a seasonal cider or two at one of the many holiday pop-up bars in the city. Each year, some of the most popular taverns in Chicago swap out their dimly lit dance floor and sports bar vibes for twinkling lights and a menu brimming with festive cocktails. 

In the Wrigleyville district of Lakeview, enter a boozy winter wonderland at Santa Baby (alter ego: Deuce’s Major League Bar), hop next door to Rudolph’s Christmas Bar (Casey Moran’s), and then finish off the night at the Hanukkah-themed establishment, 8 Crazy Nights (The Graystone Tavern).

Want a bird’s-eye view of the city? The London House in Downtown Chicago is much closer than the North Pole but offers spectacular sights from its seasonal lounge rebranded as Rudolph’s Holiday Rooftop. Whether it’s a Christmas beer that strikes your fancy or just a plain old Miller Lite, Chicago’s holiday bar scene is enough to make anyone’s spirits bright.

4. Explore ZooLights at the Lincoln Park Zoo

If you’ve spent any significant time in Chicago during winter, you’ve likely heard locals buzzing about booking their tickets to ZooLights. The Lincoln Park Zoo’s festive experience is free on certain dates, and only $5 for general admission on others. Complete with a dazzling 18-foot tree and hundreds of light displays, this popular event is the perfect way to get in the holiday spirit as you stroll throughout the zoo’s gorgeous grounds.

Enjoy spiced wine, seasonal beers, cocktails, s’mores, and more with the various snack and drink vendors scattered along the trails. Plus, you’ll be in the heart of the Lincoln Park neighborhood, which means countless options for good food and beverages before or after your visit to ZooLights.

5. Catch a performance of “A Christmas Carol” at the Goodman Theatre

The Goodman Theatre’s adaptation of Charles Dickens’ “A Christmas Carol” is a holiday tradition in its fifth decade, “enjoyed by nearly two million theatergoers” since its debut. As one of the oldest theaters in the city, The Goodman is an acclaimed organization that continues to make its mark on Chicago’s arts scene all year round. For the majority of the year, you can catch a diverse range of plays and performances at this venue located in Downtown Chicago’s Loop district.

During the holiday season, the classic tale of Ebenezer Scrooge comes to life through a performance heartwarming enough to melt even the iciest of souls. “A Christmas Carol” reminds audiences about the true meaning of the holidays and being thankful for all that we have. Anyone living in Chicagoland should experience the magic of Downtown Chicago during the holidays, and grabbing tickets to this show can make your time in the city even more memorable. 

6. Grab tickets to “The Nutcracker” at the Joffrey Ballet

Immerse yourself in the world of dance with the gorgeous performance of “The Nutcracker,” presented by the internationally known Joffrey Ballet. This Chicago staple is a great addition to your holiday bucket list, with performances running through the entire month of December.

This year, the company takes the stage at the Lyric Opera House, one of the most historic buildings in the city. Whether you are a seasoned dancer yourself, or someone new to live theatre, the Joffrey’s rendition of “The Nutcracker” is a spectacular winter experience, complete with a lavish set and breathtaking music and movement.

7. Ice skate in Downtown Chicago at Millennium Park or Maggie Daley Park 

When chilly weather strikes, there is only one thing to be done: ice skating in Downtown Chicago! Located along Michigan Avenue in the heart of the city lies some of the best seasonal ice skating experiences you’ll find. Renting a pair of skates at the McCormick Tribune Ice Rink at Millennium Park has become a popular pastime during colder months. Here, you get some of the best views of towering skyscrapers and a close-up of Chicago’s iconic Cloud Gate sculpture (otherwise known as “The Bean”).

At the neighboring Maggie Daley Park, there is also an outdoor rink. This one throws tradition to the curb and puts guests on a winding, whimsical “ribbon” rink, where you can skate through an illuminated path.

8. Check out Downtown Chicago’s holiday decorations

Whether it’s your first or your 50th holiday in the city, a stroll along State Street to view yuletide decorations is a must. Stop by Macy’s to take a gander at their annual window displays, and then walk a few blocks over to the Art Institute, where you can find their lion sculptures perched regally with garland wreaths.

To end your journey, head to Millennium Park to take in the 51-foot blue spruce, shining bright as Chicago’s official Christmas tree

9. Head to the suburbs for Illumination: Tree Lights at the Morton Arboretum 

Grab your reindeer and sleigh (your car or the train work, too) and head west of the city into the cozy suburb of Lisle, Illinois. Here you will find the Morton Arboretum, the town’s pride and joy, which spans over 50 acres of land and boasts over 100 endangered tree species. Their holiday festivities are something you won’t want to miss, combining nature and conservation with festive light displays, music and sounds, and plenty of holiday spirit!

Grab your cup of hot cocoa and roam the paths of Illumination: Tree Lights at The Morton Arboretum, a walking experience that highlights the beauty of winter. Those who prefer to swap their cocoa for a beer can snag a spot at one of the special 21+ nights, known as IllumiBrew.

10. Stroll through the Chicago Botanic Garden’s Lightscape

If you haven’t had your fill of lights quite yet, head to Glencoe, Illinois, a suburb on the North Shore, where the Chicago Botanic Garden resides. The holidays are when the Garden puts on its annual Lightscape event, an outdoor experience boasting light displays, holiday tunes, photo ops, and an illuminated zen garden. 

Lightscape nights are open mid-November through early January and are well worth your ticket if twinkling lanterns and merry carols are your thing.

11. Venture to Jack’s Winter Walk Pop-Up & Christmas Tree Farm

Pumpkin patches and Christmas tree farms are far and few in urban areas. That’s why during fall, Chicagoans can head to Jack’s Pop-Up Pumpkin Patch, situated in the Goose Island corridor of the city. Once Halloween comes and goes, the grounds are replaced with the marvelously merry Jack Frost Winter Walk Pop-Up, a fully functioning Christmas Tree farm. Don’t be fooled—this is a place where you can purchase a Canadian balsam fir for your living room, but it’s also an outdoor holiday bar with seasonal cocktails, ice skating, axe throwing, bumper cars, and plenty of photo ops for your holiday card.

12. Keep an eye out for the holiday train 

Chicago during the holidays has major North Pole vibes, and not just because of those chilly temperatures. The city’s primary mode of public transportation is its elevated subway system (known as the “L”) which transforms one of its trains into a dazzlingly jolly holiday train that rivals the Polar Express itself. 

Starting after Thanksgiving, while you’re on the L platform, you may catch a glimpse of the holiday train pulling into your station. The festive decked-out train is hard to miss and rotates each rail line throughout December. The Chicago Transit Authority’s (CTA) gift to passengers during winter makes commuting in the cold a lot more magical—even for the grinchiest of travelers! 

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Kailey Hansen

Kailey Hansen is a freelance writer and communications professional based in the land of deep-dish pizza. She has lived in both the city and the suburbs of Chicago and enjoys writing about the amazing things the Windy City has to offer. When she's not dishing about the best places to grab a slice of deep-dish, you can find her writing (and obsessing) about binge-worthy TV shows for BuzzFeed and why cats are the best (and absolutely outlandish creatures) for Rover's blog, The Dog People.