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Frosty's Christmas Bar
Photograph: Courtesy WeLovePopUps.com

The best holiday pop-up bars in Chicago

Get in the holiday spirit at Chicago's top holiday pop-up bars

Emma Krupp
Written by
Emma Krupp
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If you're looking for the perfect place to grab a nightcap after touring displays of Christmas lights in Chicago, turn your attention to the many festive pop-up bars that are setting up shop in the city this winter. Housed within some of the best bars in Chicago, these seasonal attractions are festooned in tinsel and string lights, offering guests boozy concoctions—from spiked hot cocoa to steaming mugs of eggnog—and plenty of festive photo ops. Ready to have a merry Christmas in Chicago? Visit the best holiday pop-up bars in Chicago and raise your Santa mug to the season. 

RECOMMENDED: The best things to do during the holidays in Chicago

Time Out Market Chicago
  • Time Out Market
  • West Loop

Embrace the spirit(s) of the season while enjoying festive tropical cocktails at Secret Sand-ta, the holiday-inspired cocktail bar inside of Time Out Market Chicago. Featuring drinks from expert mixologist Paul McGee (Lost Lake, Milk Room), this speakeasy-style pop-up operates out of window on the second floor of Time Out Market Chicago. Just head upstairs and look for the festive decorations, then hop in line to order a Hot Buttered Rhum Cider, a North Pole Nog or another drink festooned with jolly garnishes. Secret Sand-ta opens at 5pm on Fridays and Saturdays. 

Holiday pop-up bars in Chicago

  • Nightlife
  • Pop-ups and food events
  • Wrigleyville

This immersive, multi-level Christmas pop-up bar boasting wall-to-wall holiday decor returns to Wrigleyville, taking over Deuce's Major League Bar during the most festive time of the year. You'll find photo-ops galore as well as drinks decked out with decorative garnishes and garlands, including large-format cocktails like the Mega Yule Mule and Jingle Juice. Feeling hungry? Feast upon festive brunch options like the holiday waffles, which come topped with whipped cream, strawberries and crushed peppermint. Don't forget to snag a reservation before you head to Santa Baby—families are welcome to stop by during the day, but after 8pm it's 21+.

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  • Things to do
  • Avondale

After taking a year off in 2020, Krampus—the folkloric creature that frightens children who have misbehaved throughout the year—returns to Avondale's DMen Tap for a Christmas pop-up that's more naughty than nice. The pop-up launches December 4 with a traditional Krampus parade featuring the marching band Environmental Encroachment (feel free to wear your best Krampus costume when you attend) before continuing on throughout the month with mulled wine, Revolution Brewing's Fist of Krampus holiday ale, gooey raclette sandwiches and plenty of Krampus themed events. 

  • Nightlife
  • Pop-ups and food events
  • Loop

Situated on the ground floor of the Chicago Athletic Association, Happy's transforms the hotel's Tank space into a holly, jolly wood-paneled dive bar serving cocktails and bar bites created by Land and Sea Dept. Admission is free and the pop-up is just a short walk from the Millennium Park ice skating rink.

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  • Bars
  • River West/West Town

Happy's expands beyond the Chicago Athletic Association for the first time this season, setting up shop in the upstairs bar at Parson's West Town with homey decor, themed slushies, TVs playing holiday movies and more cheerful fun. Keep an eye out for seasonal programming throughout the month of December, like a live performance of Vince Guaraldi's "A Charlie Brown Christmas." 

  • Bars
  • Avondale

Sick of the cold? Pretend you're celebrating the season somewhere tropical at Lost Lake's annual holiday party, which fills the bar with colorful tinsel, string lights and some of the city's most delightful winter cocktails. Choose from returning favorites like the Little Saint Nog (Fiji rum, spiced demerara, cream, whole egg and three types of sherry) or sample new creations like Down Through the Chimney (mezcal, sweet vermouth, amaro, cold brew, oat milk and mole bitters). Walk-ins and reservations are accepted. 

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  • Bars
  • North Center

Indulge in a little childhood nostalgia at this pop-up bar that pays homage to Rudolph the Red-Nosed Reindeer & the Island of Misfit Toys. Hosted by The Rambler in North Center, Misfit Christmas opens with an outdoor scene decorated by 10-foot, custom-painted wood characters from the Island of Misfit Toys; inside, every room of the bar corresponds with a different scene from the movie (like the snowy forest where Rudolph and Hermey meet and sing "We're a Couple of Misfits"), and the bar's heated and covered beer garden will turn into "Santa's workshop." Top off the experience with a festive cocktail and bites from a themed food menu. 

  • Bars
  • Wrigleyville

Looking for another place to celebrate the season in Wrigleyville? The creators of the popular Santa Baby Christmas Bar also run Rudolph's Christmas Bar, located just down the street at Casey Morans. Like its counterpart, the space is decked out in over-the-top, glittering decor and a near-identical menu full of holiday-themed drinks and food. 

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  • Things to do
  • Lake View

Chicago's only Hanukkah-themed pop-up bar takes over The Graystone Tavern in Wrigleyville for a third year, filling a weatherproof patio with more than 14,000 blue-and-white lights, dreidel ornaments, lighted menorah and a Hanukkah sweater wall (among other festive bits of decor). Dine on Hanukkah classics like latkes and matzo ball soup alongside not-so-classic options like a brisket egg rolls and a boozy, vodka-infused jelly donut. Pair your meal with a novelty cocktail—we're going with the strawberry puree-flavored Mensch Mule. Chag Sameach! 

  • Nightlife
  • Pop-ups and food events
  • River North

Frosty's Christmas Bar near Goose Island brings three levels of festive fun, four bars, two dance floors, life-size toy soldiers and a themed soundtrack that keeps the crowd bumping until 4am every night of the week. Don your favorite holiday attire and enjoy a glass of something boozy and marshmallow-topped while eating Christmas cookies amid the twinkling lights, tinsel and over-the-top decorations. 

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  • Bars
  • West Loop

The sprawling outdoor space at Lou's Backyard in the West Loop gets dressed up for the holidays with string lights, Christmas trees, inflatable snowmen and more whimsical touches. Pose for photo ops, order from the seasonal food menu (including options like chef's s'mores pie topped with melted chocolate raspberry coulis) or warm up with a themed cocktail or two—the Verte Chaud, which pairs housemade hot chocolate with Green Chartreuse and a blend of winter spices, is an especially cozy choice. 

  • Bars
  • Lake View

The 2003 holiday movie Elf takes center stage at this Wrigleyville pop-up located inside of Stretch Bar & Grill, which gets dressed up with more than 1,000 decorative elves, Christmas trees and plenty of festive Christmas lights. Take a seat at tables stocked with the four main food groups (candy, candy canes, candy corn and syrup) and treat yourself to a plate of Buddy's breakfast cereal (spaghetti loaded with maple syrup, chocolate fudge and syrup, mini marshmallows and strawberry frosted pop tarts) or a mug of build-your-own boozy hot chocolate. Want to catch a glimpse of Buddy the elf himself? Visit the pop-up between Thursday and Sunday, when he's known to make appearances from time to time. 

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