The city is alive with holiday cheer! Check out some of Chicago’s most festive and immersive holiday experiences this year. Whether you’re looking for a fabulous spot to snap holiday photos or love trying colorful holiday-themed cocktails at pop-up bars with friends, we’ve got you covered.
See Also: 27 Fab Holiday Gifts Chosen By Chicago's Top Tastemakers
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Dates: Nov. 17-Dec. 24
Daley Plaza, 50 W. Washington St. / Website
Widely considered one of the city’s most beloved holiday traditions, this bustling marketplace in the heart of the Loop tempts families, couples and visitors alike to indulge in hot cider and glühwein (mulled wine), browse holiday vendors and soak up the convivial atmosphere.
Dates: Nov. 16-Dec. 3
170 N. Dearborn St. / Website
A beloved Chicago holiday tradition, Goodman Theatre’s A Christmas Carol, makes a triumphant return to the stage this season, transporting its audience to a frosty Christmas Eve in 19th-century London. The heartwarming Charles Dickens tale is brought to life with exquisite costumes, eye-popping effects and a legendary performance by veteran actor Christopher Donahue as Ebenezer Scrooge.
Dates: Dec. 6-28
20 N. Upper Wacker Drive / Website
Reimagined in 2016 by Tony Award-winning choreographer Christopher Wheeldon, the critically acclaimed Joffrey Ballet’s The Nutcracker draws an all-ages crowd to its home at the historic Lyric Opera House. Tchaikovsky’s iconic score relocates young Marie at the Chicago World’s Fair of 1893 before she embarks on a whirlwind adventure with the Nutcracker Prince in dance. The Lyric Opera House brings a grand flair to the premiere ballet performance with large-scale animated projections and a renowned orchestra performance.
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Date: Jan. 12
11 N. State St. / Website
Returning for another holiday season, Macy's 57th Annual Holiday Windows showcase the store's beloved holiday displays. The windows feature intricate scenes and festive decorations, maintaining their status as a highlight of the city's holiday season.
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Dates: Through Jan. 5
401 E. Wacker Dr. / Website
The St. Regis Holiday Atelier is a luxurious pop-up boutique that transforms the hotel’s grand lobby into a winter wonderland. This shoppable experience features an exclusive collection of holiday gifts, including St. Regis ornaments, custom beanies from Love Your Melon, Panettone from Roy and bespoke loungewear by Tom Adam. The boutique also offers curated candles, house-made confections and festive treats for children through the Candy Cart Experience.
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Dates: Nov. 29-Dec. 31
170 N. Green St. / Website
This Fulton Market pop-up offers a festive holiday experience with ice skating, bumper cars, Christmas cocktails and photo opportunities. Visitors can enjoy a multi-sensory adventure featuring a striking light display and a Christmas-themed atmosphere perfect for creating Instagram-worthy memories.
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Dates: Nov. 27-Jan.2
3640 N. Clark St. / Website
Big Star's Wrigleyville location is hosting a holiday pop-up inspired by Chappell Roan's "Pink Pony Club," featuring festive decorations like a Christmas tree adorned with pink cowboy hats. The menu includes new items like Smokey Brisket Nachos and Cowboy Coffee, a bourbon-infused drink, alongside honky-tonk tunes with a mix of Christmas music and modern country classics.
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Dates: Nov. 21-Jan. 5
3505 N. Clark St. / Website
Visit this over-the-top holiday-themed bar for multiple levels of holiday photo opportunities. There’s an immersive rooftop perfect for snapping pictures and 10 distinct sets throughout the bar. In addition, there’s a hefty menu of holiday-themed food and drinks, like “reindeer” wings, the “Clausmo” cocktail and “elf”-fashioneds.
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Dates: Nov. 29-Dec. 6
1616 N. Wells St. / Website
The Second City delivers its signature blend of sharp humor and unscripted improv in this holiday-themed revue, packed with festive songs, sketches and plenty of spontaneous comedy, all while poking fun at holiday traditions, office parties and classic Christmas staples.
See Also: The 7 Best Holiday Events On The North Shore
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Dates: Through Dec. 22
The Dawson, 730 W. Grand Ave. / Website
Back for its second year, the ‘Mistletoe & Mischief’ Pop-Up at The Dawson transforms the beloved River West restaurant into a winter wonderland. The heated, enclosed patio is decked out with festive decor, where guests can sip on holiday cocktails like the Figgy Pudding Old Fashioned and Polar Express Martini, and enjoy seasonal bites like Mrs. Claus’ Cheese Curds and Short Rib Sliders.
Dates: Nov. 29-mid Feb.
200 N. Columbus Drive / Website
Explore the hotel’s entirely transformed, holiday-decked lobby for cozy vibes and seasonal cocktails. With numerous indoor fire pit-inspired tables and a seasonal menu filled with sweet and savory fondues, decadent housemade s’mores, espresso martinis and specialty hot chocolate, the lodge is a festive spot to spend the evening.
Dates: Dec. 7-29
521 N. Rush St. / Website
The Gwen Hotel is offering a Grinch-themed Tipsy Tea throughout December, featuring tea-infused cocktails, small bites and a DJ. The event, held on weekends, combines traditional high tea with a lively atmosphere, including music and a festive vibe. It's a high-energy twist on the classic tea experience, complete with holiday-themed treats and drinks.
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Dates: Nov. 29-Jan. 5
108 E. Superior St. / Website
Offering a festive afternoon tea beneath a 20-foot Christmas tree, The Peninsula Chicago features a traditional English tea menu with a selection of finger sandwiches, seasonal pastries, and vegan and gluten-free options. Daily entertainment is provided by a string duo, with weekend appearances by Santa.
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Dates: Nov. 15-Dec. 29
203 N. Wabash Ave. / Website
In a collaboration with Bucket Listers and Mariah Carey, Virgin Hotels is launching Mariah Carey’s Black Irish Holiday Bar across the U.S. The pop-up features festive cocktails with Carey’s Black Irish liqueur, immersive holiday decor, photo opportunities and interactive elements like a "letters to Mariah" station.
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Dates: Nov. 16-Dec. 24
310 N. Green St. / Website
Punch Bowl Social in Chicago’s Fulton Market District is hosting a holiday pop-up in partnership with The Ugly Christmas Sweater Shop, featuring a selection of new and upcycled holiday sweaters. Guests can enjoy seasonal cocktails, shareable dishes, festive decor and games such as bowling, karaoke and arcade games.
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Dates: Nov. 18-Dec. 24
900 N. Michigan Ave. / Website
Visitors can experience a magical holiday setting with a 50-inch tree, a digital canopy with festive displays, and photo opportunities with Santa in a vintage sleigh. Reservations include a keepsake digital photo, a designer-inspired winter wonderland backdrop and a plush toy from Santa (while supplies last).
Dates: Nov. 22-Dec. 30
213 W. Institute Place / Website
The Reindeer Games Christmas popup returns with new holiday décor, themed cocktails and signature events. Visitors can enjoy festive photo opportunities, including a full-sized sleigh and Naughty or Nice thrones, while immersing themselves in a holiday wonderland.
Dates: Throughout December
2834 River Road, River Grove / Website
Tiki lovers will want to make the trip outside the city to this tropical pop-up bar dreamt up by industry legend Jeff “Beachbum” Berry and appearing this holiday season at iconic northwest suburban watering hole Hala Kahiki Tropical Lounge. Expect kitschy, festive decor and themed cocktails like the Surf Nut, Sharkey's First Christmas and the Ginger Snapper.
See Also: The 7 Best Holiday Lights Displays In Chicago
Dates: Dec. 6-22
3635 N. Clark St. / Website
From family-friendly activities, interactive experiences and the Wrigleyville Christkindlmarket at Gallagher Way to skating inside historic Wrigley Field at the Gallagher Ice Rink, this Lakeview event has fast become a North Side holiday tradition.
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Dates: Dec. 7-24
The Music Box Theatre, 3733 N. Southport Ave. / Website
Each year, Santa Claus leads the audience in carol singing, accompanied by the theater’s organist, before a classic Christmas movie is shown. Attendees can enjoy films like White Christmas or It’s a Wonderful Life, with some choosing to see both for a full holiday experience.
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Date: Dec. 7
The Auditorium 50 E. Ida B. Wells Drive / Website
Featuring the Chicago Philharmonic Orchestra performing Craig Armstrong’s stirring score live, the Love Actually Film in Concert brings the beloved holiday classic to life. Set in London during the Christmas season, the film intertwines multiple love stories, from the romantic to the bittersweet, capturing the chaos and joy of relationships during the holidays.
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Date: Dec. 10
220 S. Michigan Ave. / Website
Featuring Chanticleer’s men’s vocal ensemble, this annual holiday concert at Symphony Center will showcase a blend of hymns, carols and festive classics. The program includes selections from Benjamin Britten’s A Ceremony of Carols and Ave Maria by Franz Biebl, along with other traditional holiday music.
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Dates: Dec. 10-15
CIBC Theatre, 18 W. Monroe St. / Website
The Hip Hop Nutcracker returns to Chicago's CIBC Theatre with a fresh take on Tchaikovsky’s classic ballet. Kurtis Blow, the founding father of hip hop, hosts this family-friendly holiday performance which features a cast of all-star dancers, an on-stage DJ and an electric violinist.
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Dates: Dec. 12-15
Steppenwolf's Downstairs Theater, 1650 N. Halsted St. / Website
Five-time Emmy-winner Jane Lynch, along with Kate Flannery, Tim Davis and the Tony Guerrero Quintet, perform in a holiday show that combines comedy and music. The group, known for their lively performances and humor, has toured nationwide, with their album A Swingin’ Little Christmas reaching the Top 10 on Billboard's Adult Contemporary chart.
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Dates: Dec. 17-18
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St. / Website
Inspired by the iconic Christmas song "Fairytale of New York" by The Pogues, this show is a festive Irish-themed concert blending traditional Christmas carols, classic Irish tunes, and the titular song. The performance focuses on singing, dancing and storytelling, capturing the song's narrative about a struggling couple in New York City during Christmas.
Dates: Dec. 18-23
Symphony Center, 220 S. Michigan Ave. / Website
A beloved tradition among families and a holiday treat for classical music fans, this performance features conductor Alastair Willis leading members of the Chicago Symphony Orchestra and the Chicago Symphony Chorus in a program filled with traditional carols and festive holiday songs. The musical selections include iconic pieces such as “Joy to the World," “Carol of the Bells” and “White Christmas.”
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Dates: Through Dec. 31
20 E. Delaware Place / Website
The Talbott Hotel has transformed its Gallery and patio into a cozy winter retreat, offering guests blankets, hot cocoa, cider and whiskey cocktails from High West Whiskey. Visitors can also enjoy tabletop s’mores and signature drinks like the Hip Flask Pioneer served in a keepsake flask.
Dates: Through Jan. 4
3632 N. Clark St. / Website
Returning for the season, Mistletoe offers a limited-time holiday cocktail menu with a mix of modern twists and vintage favorites. Located across from Wrigley Field, the venue is decked out in immersive holiday décor, creating a festive atmosphere for gatherings, nights out or cozy date nights.
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Dates: Through Jan. 5
435 N. Clark St. / Website
Three Dots and a Dash is transforming its River North space from a tropical paradise to a winter wonderland for the holiday season. The bar features festive decorations, a specialty holiday cocktail menu with hot drinks and themed sippers and unique glassware including a Snowman mug for collectors.
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Dates: Through Jan. 5
85 E. Wacker Drive / Website
LondonHouse Chicago offers a unique afternoon tea experience at the Bridges Lobby Bar, featuring a selection of Rare Tea Cellars and Sparrow Coffee teas, fresh scones and a three-tiered tower of savory and sweet bites. Designed by Executive Chef Elizabeth Sweeney and Executive Pastry Chef Thomas Gorczyca, the menu highlights crafted offerings, with accommodations for common dietary restrictions, though substitutions for specific aversions are not available due to the intricacies of the kitchen.
While you’re at LondonHouse, head up to its Rudolph’s Rooftop experience on the 22nd floor. The immersive, over-the-top bar features rentable outdoor igloos, a frosty ice bar and numerous Insta-worthy holiday-themed photo opportunities.
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Dates: Through Jan. 15
435 N. Michigan Ave. / Website
Head to the Museum of Ice Cream for a colorful journey through the destination’s signature Pinkmas exhibit. Along with the iconic sprinkle pool, the Pinkmas celebrations will include a bevy of interactive moments, like wandering through a Pinkmas tree forest, snapping photos in an Insta-worthy life-sized snow globe and sampling holiday flavors and treats along the way. Guests can upgrade their ticket with seasonal ice cream sundaes and (for guests over 21) holiday cocktails, too.
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Dates: Multiple dates throughout Dec.
50 E. Erie St. / Website
Putting its own ‘gilded’ spin on the holiday season, the Driehaus Museum presents "Drie-cember," a month-long celebration with family-friendly events. Highlights include the Photographing Frank Lloyd Wright exhibition, holiday concerts and Yuletide-themed ghost stories. This year, the newly reopened Murphy Auditorium hosts a festive Holiday Market featuring artisanal goods from local vendors.
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Dates: Through 2025
111 N. State St. / Website
One of Chicago’s most longstanding holiday traditions is a festive meal in Macy's iconic 7th-floor Walnut Room, which this year will be decked out with the Great Tree, a stunning 45-foot Christmas tree hanging from the ceiling and decorated to the hilt.
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Dates: Nov. 30-Dec. 22
323 E. Upper Wacker Drive / Website
Hosting its eleventh season, Swissotel Chicago's Santa Suite transforms the 2,000-square-foot Presidential Suite with over fifteen trees and holiday surprises. The suite, filled with festive treats and hot cocoa, offers views ideal for Santa to monitor the weather before Christmas Eve.
Photography by: Tinsel photo by megaflopp / Getty Images; Fairmont Lodge photo by Jared Powell; Martha May's Merry Tipsy Tea Party photo by Gene Yoon; Immersive Nutcracker photo by Margo Hawk; Nutcracker photo by Cheryl Mann; Second City photo by Timothy M. Schmidt; A Christmas Carol photo by Liz Lauren; Sippin' Santa photo by Randy Schmidt; 'Twas the Night Before... photo by Errison Lawrence; Lights Festival photo by Vito Palmisano; Chocolate Bar at The Pen courtesy of The Peninsula Chicago
