I LOVEย a holiday pop-up bar! Itโs 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 Daddyโs Holiday Pop Up
3636 N Clark Street, Chicago
November 25th – End of Year
Details: Wrigleyville will transform into Smoke Daddyโs 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 dรฉcor, 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 Rinkโthereโs something for everyone!
And the fun doesnโt 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 Pierโs holiday lights.
Frostyโs Christmas Bar
Frostyโs Christmas Bar
809 W Evergreen Avenue, Chicago
November 15th – December 30th
Details: 4 bars, 3 levels, 2 dance floors, and endless Christmas fun. Frostyโs only appears once a year for 6 short weeks. Featuring life size nutcrackers, sexy Santaโs and elves, and non stop holiday music spinning, this is the ultimate seasonal experience you donโt 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 Chicagoโs 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 Chicagoโs 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 Riverwalkย
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 Shulaโs Steak House. The immersive experience reimagines Shulaโs private dining room as a cozy retreat filled with twinkling lights, faux snow, nostalgic dรฉcor, and sleigh-inspired photo opsโoffering one of Chicagoโs most cheerful backdrops for cocktails, celebrations, and family gatherings.
BigStar
Big Star Wrigleyvilleโs 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 Chicagoโs most *sparkly* holiday attractions, Big Star Wrigleyvilleโs Holiday Honky Tonk is back and bigger than ever.
Returning for its second season, James Beard Awardโwinning One Off Hospitalityโs 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. Itโs 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.
