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
108 W. Germania Place / Website
Dates: Nov. 24-Dec. 30
Get into the holiday spirit at this 21-and-over holiday pop-up bar experience. This immersive wonderland features holiday scenes, themed cocktails and live entertainment, plus daily prizes from the Advent calendar. Opens Nov. 24; purchase tickets here.
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Daley Plaza, 50 W. Washington St., / Website
Dates: Nov. 17-Dec. 24
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.
Auditorium Theatre, 55 E. Ida B. Wells Drive / Website
Dates: Nov. 25
The cult classic Will Farrell holiday flick gets the symphonic treatment in the iconic Auditorium Theatre, as a live symphony orchestra performs renowned composer John Debney’s heartwarming score as the entire film is projected on a 40-foot HD screen.
200 N. Columbus Drive / Website
Dates: Nov. 20-February 2024
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.
A scene from The Second City’s 2021 holiday show Deck the Hallmark
230 W. North Ave. / Website
The Second City brings its signature brand of cheeky wit and no-holds-barred improv to this holiday show, which skewers family gatherings, office parties, classic holiday movies, and "Queen of Christmas" Mariah Carey’s with a mix of songs, sketches and laugh-out-loud hijinks.
Larry Yando makes an unforgettable Scrooge in Goodman Theatre’s A Christmas Carol.
170 N. Dearborn St. / Website
Dates: Nov. 18-Dec. 31
A beloved Chicago holiday tradition, Goodman Theatre’s A Christmas Carol makes a triumphant return to the stage this season for its 44th annual production, 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 Larry Yando as Ebenezer Scrooge.
108 W. Germania Place / Website
Dates: Nov. 24-Jan. 7
After an acclaimed 2022 debut, The Immersive Nutcracker, A Winter Miracle is bringing back its eye-popping take on E.T.A. Hoffman's 1816 fairy tale, The Nutcracker and the Mouse King. The family-friendly, 30-minute immersive experience features whimsical animated characters alongside footage of professional ballet dancers; set to the familiar music of Peter Ilyich Tchaikovsky, the footage is composed of over 1 million frames of video across 500,000 cubic feet and includes beloved numbers like “The March of the Toys,” “The Dance of the Sugar Plum Fairy” and more. Tickets from $24.99
20 N. Upper Wacker Drive / Website
Dates: Dec. 2-27
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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85 E. Wacker Drive / Website
Dates: Nov. 18-Jan. 14
Enjoy stunning views of the Chicago River as you treat your crew to an adorable afternoon holiday tea service, complete with a mouthwatering array of baked goods and teas. On the menu, choose from black, green, chai, flower, and herbal teas from Rare Tea Cellars, in addition to a basket of dark chocolate cherry scones, candied orange scones and vanilla citrus Madeleines. Savory items include viet tofu crisps and a sunchoke latke, which will be served on a photo-worthy three-tier display. There’s even a dedicated children’s menu so the whole family can take part in this holiday treat. The tea service is priced at $90 per adult and $45 per child under 10. Reservations for up to five guests can be placed here.
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.
Symphony Center, 220 S. Michigan Ave., / Website
Dates: Dec. 16-23
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.” Symphony Center’s holiday tradition promises to create cherished memories for your entire clan.
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11 E. Walton St. / Website
Dates: Nov. 19-Dec. 25
In the heart of the Gold Coast, Brass Tack at Waldorf Astoria Chicago is transformed by this international holiday pop-up into a whimsical winter wonderland complete with quirky decor, creative cocktails and a convivial vibe. See here for complete information.
3632 N. Clark St. / Website
Dates: Nov. 17-Jan. 6
Back for a fifth year, this festive holiday pop-up at Wrigleyville cocktail fave Mordecai transforms the second-floor lounge into a warm and welcoming hideaway of over-the-top holiday decor and smart libations like gingerbread milk punch and a winter Old-Fashioned accented with maple and winter forest bitters.
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435 N. Michigan Ave. / Website
Dates: Nov. 17-Jan. 15
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.
213 W. Institute Place / Website
Dates: Nov. 16-Dec. 31
With over-the-top holiday decor (including plenty of photo-op spots), themed cocktails like Santa’s Slushie and the Fireside Old-Fashioned, and of course vintage and new video games galore, this River North arcade bar’s festive pop-up is all but guaranteed to get you into the ho-ho-ho spirit.
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3505 N. Clark St. / Website
Dates: Nov. 17-Jan. 7
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, to name just a few. Tickets required for photo opp space and can be purchased here.
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900 N. Michigan Ave. / Website
Dates: Nov. 18-Dec. 24
One of the Mag Mile’s premier shopping destinations welcomes St. Nick for photo ops throughout the holiday season. Reservations can be made here, and visits include a keepsake digital photo, a special toy from Santa, three hours of free parking and more, all against a winter wonderland backdrop of the festively decked-out 900 North Michigan Shops. Be on the lookout for Tommy, the Real Elf, who'll be making appearances throughout the season.
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12 S. Michigan Ave. / Website
Dates: Friday, Dec. 8 and Saturday, Dec. 9 from 5 p.m. to 10 p.m.
Explore all the best local shops and businesses Chicago has to offer with this expansive makers’ holiday market held at the Chicago Athletic Association. With over 40 local food, art and retail vendors, there’s a wide variety of gifts to shop for your whole gift list. From Soothsayer Hot Sauce to Funeral Potatoes to Roe & Co Irish whiskey, the market will offer gifts for lovers of food, art and more. Check out the outfit's Instagram page to learn more about vendors coming to the market.
2834 River Road, River Grove / Website
Dates: Nov. 21-Dec. 31
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.
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323 E. Upper Wacker Drive / Website
Marvel in the fanciful decor of a holiday jewel-themed set of rooms, held in Swissotel’s expansive 2,000-square-foot presidential suite. Within, find 17 glistening Christmas trees decked out to represent the 12 birthstones and abundant with ornaments, berries, intricately woven ribbons and jewelry boxes, with faux jewel garland rounding out the effect. Tour the space with your crew or book it for a private event with Santa or a slew of other holiday activities.
The Chicago Theatre, 175 N. State St. / Website
Dates: Dec. 7-28
Based on the classic poem “A Visit from Saint Nicholas” by Clement Clarke Moore, Cirque du Soleil’s first holiday show tells the story of a young girl who rediscovers the magic of the holidays and features the troupe's signature jaw-dropping acrobatics, quirky characters, and a soundtrack that reimagines holiday classics.
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111 N. State St. / Website
Dates: Nov. 4-Dec. 31
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 for the 116th time with the Great Tree, a stunning 45-foot Christmas tree hanging from the ceiling and decorated to the hilt. Pro tip: Reservations fill out lightning fast, so book your table—and your visit to Santa in Macy’s Santaland—ASAP.
3635 N. Clark St. / Website
Dates: Nov. 21-Jan. 7
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. Regular entry tickets start at $5 (free entry for children ages 2 and under); Peppermint Pack attraction bundles $30, including Wrigley Field admission and 10 attraction tickets redeemable for all rides and games.
401 N. Michigan Ave. / Website
Dates: Nov. 18, 11 a.m.-7 p.m.
More than one million visitors gather on North Michigan Avenue for this beloved annual festival, now in its 32nd year. After a day of family activities and live music, the parade kicks off at 5:30 p.m. led by Grand Marshals Mickey Mouse, Minnie Mouse and other Disney friends as they light a million lights on 200 trees along the Mag Mile, followed by 40 floats, giant helium balloons and live music acts like Sister Sledge and The Sugarhill Gang. This year, guests are invited to wear holiday sweaters to join an attempt to break a world record for the most holiday sweaters in one gathering. The event with an over-the-top fireworks show and marks the official kick-off to Chicago’s holiday season.
Photography by: Tinsel photo by megaflopp / Getty Images; Fairmont Lodge photo by Jared Powell; 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
