1. Sample Delicious German Treats & Shopping at Christkindlmarket
In Chicago, an authentic, German Christmas market is never more than a short drive away. Just head on over to Daley Plaza, where the smell of roasting nuts and the sound of merry carolers converge for Christkindlmarket. Here you'll find a collection of artisan goods, live music, and freshly baked pretzels speckled throughout a warmly lit maze of wooden vendor booths.
Peruse the selection of handmade wares to find the perfect ornament for your Christmas tree, or sample the array of hot cheese and juicy sausages. Admission to Christkindlmarket is free of charge. So, you can join in just to enjoy the joyful vibes at this beloved Chicago Christmas market.
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2. Test Your Ice Skating Skills at Millennium Park
The satisfying slice of skates on ice is one of the first signs that winter has arrived at last. For Chicagoans, a trip to the Millennium Park ice rink is a seasonal tradition to be savored until spring settles its warm breath around the city. Zigzag across the icy enclosure, as giant faces flash across the Crown Fountain.
Swing by for a daytime spin around the rink and catch a glimpse of The Bean lightly blanketed with snow. Or, opt for a nighttime skate. You'll be illuminated by trees dressed up to the nines in their twinkling holiday attire. Admission is free, and stake rentals are available for winter visitors.
3. Light Your Holiday Spirit With a Holiday Lights Tour
Chicago gets brighter as the holidays near, with a little help from millions of tiny bulbs. Countless strings of Chicago Christmas lights enchant the city after dark, effortlessly imbuing each street with the holiday spirit, culminating in the festive Chicago parade.
To ensure you don't miss a single display, hop aboard a holiday lights tour this season. Whether you travel by foot, trolley, or Segway, you'll find yourself engrossed in the passing gleam of glittering lights in a careful arrangement of vibrant colors. Or, grab yourself a hot drink and embark on a self-guided tour as you take in the collective jubilee evoked by each sparkling strand.
4. Catch The Nutcracker at a Local Theater
A classic tale of mice, fairies, and Christmas spirit, The Nutcracker is a longstanding holiday tradition that consistently has families flocking to the theater. See the iconic ballet for yourself at any one of Chicago's venues, including the Harris Theater and the Lyric Opera House.
Once you've honored the tradition, head to The Chicago Theatre to experience 'Twas the Night Before..., one of our performances that serves up a heartwarming Christmas tale with an acrobatic twist.
5. Celebrate Christmas Around the World at the Museum of Science and Industry
Holiday customs come together in the melting pot that is Chicago. To honor the city's diversity and showcase the broad group of cultures within, each year the Museum of Science and Industry hosts an illustrious Christmas Around the World display.
Located on the outskirts of Hyde Park, the exhibit features a forest of over 50 Christmas trees, each uniquely decorated to represent a different culture and arranged to encircle a magnificent four-story Grand Tree. This holiday tradition has wowed spectators for over 75 years and remains a cherished citywide celebration that reflects the fantastically diverse makeup of its own community.
6. Gaze Into Holiday Window Displays on State Street
Shopping for the perfect Christmas gift is almost as fun as watching your loved ones tear into the colorful packaging. Start your holiday shopping spree by walking the Lakefront Trail in Maggie Daley Park on a journey to State Street, where you'll find everything from historic department stores to locally-owned specialty shops. And finish with Fulton Market in the West Loop.
As you peruse the street, take in the famed window displays on full view for the passing public. Inaugurated by the State Street Macy's in the 1870s, the tradition has caught on with neighboring stores, all of which take great pride in supplanting their windows with lush Christmas trees, animatronics, and scenic snow-capped landscapes so beautiful you'll forget what you were shopping for.
7. Start a New Tradition With ‘Twas the Night Before
'Twas the Night Before is our first holiday show, based on the classic poem “A Visit from Saint Nicolas” by Clement Clarke Moore. Memorable lines from this cherished classic inspired our story about a jaded young girl who rediscovers the magic of the holidays.
A joyous celebration of love and happiness designed with families in mind, ‘Twas the Night Before showcases exhilarating acrobatics, endearing characters, and a musical score that breathes new life into beloved holiday classics.
8. Attend a Holiday Concert Hosted by the Chicago Symphony Orchestra
Few things are more joyous than a symphony orchestra. During the holidays, the triumphant voice of a brass section and the spirited clang of the bells are musical embodiments of the season. Each performance delivers an emotionally charged exercise in nostalgia and presents goodwill.
All winter long, the Chicago Symphony Orchestra shares its glorious cheer with gleeful holiday-themed performances the entire family can enjoy. Take your seat at the Merry, Merry, Chicago! show for symphonic renditions of Christmas favorites new and old.
9. Decorate a Gingerbread House
The sweet and spicy taste of gingerbread is a quintessential Christmas flavor, one that's best served in the shape of a miniature cottage. Decorate your own edible abode at gingerbread workshops across the city, where you'll be given blank cookies and all the confectionery decor your creative heart desires. It's everything you need to craft a perfectly habitable home for your cookie family.
Workshops such as those hosted by Aster Hall and the Park Hyatt Chicago, which is just above River North, come stocked with snacks and drinks to graze on as you flex your creative muscles on a canvas made of sugar, spice, and flour.
10. Head to Winter Wonderfest at Navy Pier
With a name like Winter Wonderfest, this holiday celebration practically screams Christmas cheer, which is exactly what it offers any visitor who enters this holiday utopia. Hosted by Navy Pier, this fun-filled winter extravaganza is a full-blown amusement park. Not to mention, it's completely indoors, so visitors don't have to brave the Windy City chill.
Complete with a Ferris wheel, an ice-skating rink, and a massive Christmas tree, Winter Wonderfest is an anticipated, annual tradition for couples and families. Plus, you'll have direct access to Light Up the Lake, which is an interactive Christmas light show that encapsulates the joyful glow of the season.
11. Go Holiday Shopping at the Magnificent Mile
Shopping trips are synonymous with the holiday season. Nowhere else in Chicago does shopping quite like the Magnificent Mile. Home to over 450 retailers, this stunning shopping center is a one-stop shop for every gift on your list.
From department stores and grocery markets to small boutiques and internationally renowned designers, the Magnificent Mile has more than earned its over-the-top title. Stroll the length of shop-filled halls and ooh and aah every step of the way.
12. Take a Festive Ride on the CTA Holiday Train
Only in Chicago does public transit earn a spot on a list of holiday attractions. Here, one of the most unique community traditions is the arrival of the Chicago Transit Authority's holiday train and bus. Sponsored by Allstate, each vehicle is dressed up in a full holiday outfit. The attraction is complete with merry music, festive scenes, and thousands of rainbow Christmas lights.
Lucky train passengers might just spot Santa Claus himself. He may be amidst an open-air flatcar carrying a collection of brightly lit trees and accompanied by his trusted reindeer. As anyone who rides the Blue Line would attest, the sight of this jolly train barreling down the tracks is a reminder of the holiday's unexpected joys.
13. Take to the Hills for Christmas Sledding
No Chicago Christmas is complete without a thrilling slide down a snow-encrusted hillside. Once the streets have seen a good dusting, you'll find plenty of hills transformed into the perfect track for your Radio Flyer.
The Dan Ryan Woods boasts a popular 200-foot hillside with stairs to ease the strain of the trek up. Also notable is the hill at Soldier Field. Although not long, its extreme steepness makes for some serious speed. For a spectacular view, head to the lakefront Cricket Hill for unforgettable activities.
14. Sip Holiday Tea at Chicago Tearooms
Holiday high tea is a burgeoning tradition among Chicagoans thanks to the city's dense population of fabulous tearooms. Lavish spots, such as The Langham and Palmer House Hilton, serve up seasonal tea times in a more traditional sense, with classically gourmet spreads featuring tasty bites, such as crab salad sandwiches and spiced gingerbread cake.
To up the pomp and circumstance, reserve a table at The Drake, whose dainty holiday pastries and ethereal harp music once hosted Queen Elizabeth. If your party includes younger tea-time attendees, the Chicago Children's Theater hosts a positively lovely Beatrix Potter-themed holiday tea party and puppet show.
15. Test Your Winter Olympic Skills at Curling by the Lake
Whatever professional players might argue, curling is best enjoyed lakeside with a hot cocktail in your free hand. At Harry Caray's on Navy Pier, this is one sport you can master in a single happy hour.
Gather a group of friends and reserve your rink for some healthy competition at this delightful restaurant, tastefully decorated in a cozy lodge style. Complete with steaming cocktails, such as spiked cider and butterscotch coffee, this is one game that's worth a night out in the chilly Chicago air.
16. Order a Giant Hot Chocolate at Bombobar
Bombobar, named after a sugar-dusted Italian donut, presents an unassuming walk-up window. Here, patissiers churn out some of the Windy City's most delicious desserts. But during the holiday season, donuts play second fiddle to one delicacy: hot chocolate. A steaming cup of Bombobar drinking chocolate is unlike any other beverage of its kind.
Dubbed the "Hotter Chocolate," each drink is decorated with a mountain of treats, from candy floss and toasted marshmallows to, of course, Italian donuts. As scrumptious as it is photogenic, the Hotter Chocolate will warm you up and leave you with a sugar rush that lasts for hours.
17. Get Moving at the Santa Hustle
Step aside Turkey Trot, it's Santa Hustle's season to shine. The annual race starts and ends at Navy Pier. There's a festive 5K loop in between, where participants can run, walk, and jingle all the way down to the finish line. Open to racers of all ages, the Santa Hustle offers Chicagoans and visitors the chance to get outdoors in a season that makes it easy to curl up under a blanket indoors.
Racers who cross the finish line are given the ideal souvenir for bragging purposes. Rather than ribbons, racers receive a comfy zip-up hoodie and a one-of-a-kind medal adorned with a swinging jingle bell.
18. Eat a Festive Meal at the Walnut Room
The world's first-ever department store restaurant is still slinging holiday meals and deals beneath a tastefully ornamented tree. Every year, the Walnut Room at State Street Macy's hosts a legendary holiday season experience inspired by its opening-day menu in 1907.
Mouthwatering dishes such as chicken pot pie, braised short ribs, and shrimp cocktails are just right to celebrate the season. Amid the wood-paneled walls and Austrian chandeliers, you'll find yourself happily enchanted by the old-world charm of this Christmas tradition.
19. Cozy Up With a Glogg at Simon’s Tavern
Simon's Tavern is a treasured dive bar among neighborhood regulars. Scott Martin made his mark on the Windy City in 1994 when he whipped up his first batch of glogg. Hailing from Nordic countries, glogg is a spicy, mulled wine served hot and toasty — the perfect beverage for icy Chicago winters.
Martin crafts his brew with fresh oranges, cardamom, and sweet yellow raisins for a soul-warming mug. And we think it's best enjoyed alongside a crisp ginger cookie. With a full belly, venture into the Woolly Mammoth Antiques & Oddities and the Chicago Magic Lounge. You'll be able to see thousands of objects appear (and disappear).
20. Indulge Yourself at Frosty’s Christmas Bar
This Chicago Christmas bar is so devoted to the season, it closes its doors when spring comes knocking. Just a hop, skip, and jump from Oz Park, Frosty's is a wild and wonderful Christmas celebration. Bartenders serve up holiday-themed drinks amidst an extravagantly festive atmosphere.
This adults-only experience leans heavily into nostalgia. It's ornamented with massive toy soldiers, garlands, and a parade of rainbow bulbs suspended over the dance floor. Grab a few friends, and dive into the Frosty's crowd for an unforgettable night of holiday drinks and laughs at this Christmas bar.
Walk in a Winter Wonderland This Christmas in Chicago
Chicago raised stars like Tina Fey and John Belushi. So, it’s no wonder it’s brimming with cheerful fun and possibly one of the most beloved cities in North America. Curl up with a comically large hot chocolate or a Chicago-style hot dog on a bench in Lincoln Park. Or, gaze across a sea of twinkling lights. These Christmas excursions in Chicago will leave you with a cache of memories lasting long after the tree comes down.
For another breathtaking holiday experience, step into our fantastical world at a theater near you. Each performance is packed with high-flying adventure and moving stories with unmatched creativity.
Give yourself the gift of wonder this Christmas. Book your tickets to one of our shows in Chicago now to catch the most imaginative show in Chicago theaters.