I LOVE a holiday pop-up bar! It’s truly the best way to get you in the holiday spirit. Grab your free and go check out on of them below.
Jack Frost Christmas Pop-Up
Jack Frost Christmas Pop Up
170 N Green Street, Chicago
November 22nd – January 3rd
Details: Cozy meets chaos in the best way possible. Ice skating, curling, bumper cars, axe throwing, and cocktails all under the outdoor lights. This pop-up is truly one of my favorites.
Smoke Daddy’s Holiday Pop Up
3636 N Clark Street, Chicago
November 25th – End of Year
Details: Wrigleyville will transform into Smoke Daddy’s Winter Wonderland, a floor-to-ceiling holiday pop-up inspired by a nostalgic 1950s Christmas at home. Guests can expect tinsel-draped walls, glowing red-and-green décor, a wreath wall ornament installation, and cozy fireside sitting areas perfect for photos.
Winter WonderFest
Navy Pier (600 E Grand Avenue, Chicago)
December 5th – January 4th
Details: Step inside and kick off the season with rides, slides, and festive fun. From thrilling attractions like the Cliffhanger and Zero Gravity to family favorites like the kiddie train, bumper cars, and skating on The Verizon | Google Pixel Ice Rink–there’s something for everyone!
And the fun doesn’t stop there. Every ticket includes a ride on the iconic Centennial Wheel, where you can soar to heights of nearly 200 feet and take in dazzling views of the Pier’s holiday lights.
Frosty’s Christmas Bar
Frosty’s Christmas Bar
809 W Evergreen Avenue, Chicago
November 15th – December 30th
Details: 4 bars, 3 levels, 2 dance floors, and endless Christmas fun. Frosty’s only appears once a year for 6 short weeks. Featuring life size nutcrackers, sexy Santa’s and elves, and non stop holiday music spinning, this is the ultimate seasonal experience you don’t want to miss.
Nut Cracker Pop Up Bar
15 W Illinois Street
November 21st – December 30th
Details: Head to River North for an over the top bar for cocktails, entertainment, and memory making.
Winterland at Gallagher Way
3635 N Clark Street, Chicago
November 23rd – December 31st
Details: The annual Winterland celebration transforms Wrigleyville into one of Chicago’s most festive seasonal destinations! Kicking off with the return of Christkindlmarket Wrigleyville, this cherished neighborhood holiday tradition fills Gallagher Way with its signature wooden huts, handcrafted gifts, and traditional German and international food and beverages.
This year, guests can experience even more holiday cheer with an expanded lineup of activities and tenant offerings, ranging from themed pop-ups and cozy dining experiences to creative workshops and an extended ice rink season running through February 15, 2026.
Fannie May Trolley
Fannie May Jolly Trolley
343 N Michigan Avenue
December 5th – December 21st
Details: All aboard! This holiday season, Fannie May is decking the trolleys with their first-ever Jolly Trolley experience, celebrating 105 years of Chicago’s rich chocolate history.
Running December 5-21, the Jolly Trolley creates a moving holiday wonderland where guests can enjoy chocolate tastings, holiday jazz renditions, and other surprises, led by our very own Taste Conductor. Decorated floor-to-ceiling with vintage holiday decor, the Jolly Trolley is the perfect way to experience the Chicago holiday magic this season.
Sheraton Grand Chicago Riverwalk
301 E. North Water Street, Chicago
November 21 – December 30th
Details: This holiday season Sheraton Grand Chicago Riverwalk transforms into a winter wonderland with the debut of Sleigh Bar, a festive pop-up presented by Shula’s Steak House. The immersive experience reimagines Shula’s private dining room as a cozy retreat filled with twinkling lights, faux snow, nostalgic décor, and sleigh-inspired photo ops—offering one of Chicago’s most cheerful backdrops for cocktails, celebrations, and family gatherings.
BigStar
Big Star Wrigleyville’s Holiday Honky Tonk
3640 N Clark Street, Chicago
November 21st – January 2nd
Details: Located just steps from the Wrigleyville Christkindlmarket at Gallagher Way – one of Chicago’s most *sparkly* holiday attractions, Big Star Wrigleyville’s Holiday Honky Tonk is back and bigger than ever.
Returning for its second season, James Beard Award–winning One Off Hospitality’s festive pop-up transforms the iconic taqueria at Gallagher Way into a glittering, cowboy-meets-Christmas spectacle: think twinkling lights, rhinestone hats, and country tunes colliding for an unforgettable holiday experience.
The Dandy Crown
A Very Dandy Holiday
Dandy Crown (694 N Milwaukee Avenue, Chicago)
November 21st – January 4th
Details: The festive holiday themed winter pop-up bar is returned for its 4th year. It’s a highly decorated, cocktail focused event with holiday cheer and decor through the interior and the outdoor enclosed and heated (dog friendly) patio. The pop-up is free to attend, and while walk-ins are accepted, reservations are highly encouraged. Additionally, several festive and free of charge events will be planned throughout the holiday season.
