‘Tis the season for holiday pop-up bars. Some of Chicago’s favorite bars and restaurants have temporarily transformed their space into full-blown winter wonderlands. Expect over-the-top decorations, seasonal cocktails, festive food specials, and plenty of photo opps at holiday-themed bars all around the city. And don’t wait — many of these seasonal extravaganzas disappear after the new year.
Celebrate the season at these festive Christmas and holiday bars and pop-ups in Chicago.
Santa Baby at Deuce’s
Nov. 17, 2022 – Jan. 13, 2023
If you want to go all in on the holidays, why not celebrate at this over-the-top Christmas experience? Santa Baby at Deuce’s in Wrigleyville features extensive decor in every inch of their space, from twinkling lights outside to ceilings crowded with glittering ornaments inside. And the boozy holiday drinks are just as extravagant — get cocktails like the Merry Mojito, Jingle Juice, and spiked hot chocolate and egg nog in individual and jumbo shareable sizes.
Book your table for inside the multi-level bar area or check out the tented patio outfitted with heaters. Make your reservations here.
8 Crazy Nights at The Graystone Tavern
Nov. 25, 2022 – Jan. 8, 2023
8 Crazy Nights, Chicago’s first Hanukkah-themed pop-up, is returning to The Graystone Tavern in Lakeview. The pop-up has taken over the bar and the enclosed, weatherproof patio, which will both be decorated with dreidel ornaments, lighted menorah decor, a photo booth, and more than 8,000 blue and white lights.
A special food menu includes traditional Jewish favorites like latkes, matzo ball soup, brisket platters, and boozy jelly donuts. There’s also a playful drink menu with cocktails, beer, and shots.
Reindeer Room at Tack Room
Nov. 25, 2022 – Jan. 1, 2023
Tucked inside historic Thalia Hall in Pilsen, the Tack Room has become the Reindeer Room for the holiday season. The cozy bar is decked out with garlands, lights, and mistletoe, with festive-themed drinks being mixed behind the bar. Order a Jingle Juice or a Mexican Hot Chocolate to sip while you enjoy the sounds of live piano every Thursday through Saturday.
Rudolph’s Holiday Rooftop at LH Rooftop
Now open
Enjoy sweeping city views and tons of holiday cheer at Rudolph’s Holiday Rooftop. Located atop the LondonHouse Chicago, this seasonal pop-up includes features festival menu items, private igloos, holiday décor, and back-drops for capturing photos. Contact rsvp@londonhouse.com to book your tables.
Tinseltown at Pink Squirrel
Now open
This cocktail spot in Logan Square, an homage to Midwestern bar culture, has been totally transformed for the holidays. Tinseltown includes wall-to-wall decorations for a truly immersive holiday experience, along with a full menu of festive treats that includes shots, cocktails, punches, and milkshakes. Guests are also invited to build their own gingerbread houses or play a few rounds of duckpin bowling.
Winter Wonderland at JoJo’s Shake Bar
Nov. 14, 2022 – Jan. 8, 2023
In River North, JoJo’s Shake Bar has launched an expansive indoor/outdoor Winter Wonderland. Grab a table and try their special holiday shakes, boozy hot chocolates, a milk-and-cookies flight, Santa-approved cocktails, and more. Don’t miss the ultra-photogenic milkshakes or the Rockin’ Around the Christmas Tree Margarita, which features a tower of festive tequila drinks. Reservations are now available indoors, in the private igloos, or on the heated patio.
Christmas Inn at Hubbard Inn
Now open through Dec. 31, 2022
The holidays are coming to Hubbard Street. The Christmas Inn is popping up in River North at Hubbard Inn, with multiple floors of decor (each with a different theme), winter cocktails, festive photo opps, and live entertainment. Upcoming events include holiday trivia night, holiday spirits mixology class, guided wine tastings, and gingerbread house decorating. Make a reservation.
Jack’s Frost’s Winterfest
Dec. 3, 2022 – Jan. 1, 2023
This outdoor winter extravaganza has something for all ages, from picking out the family Christmas tree to sipping boozy holiday drinks. Jack Frost’s Winterfest on Goose Island invites guests to enjoy carnival games, ice skating, axe throwing, bumper cars, music and lights, seasonal drinks, and more. Plus, there are plenty of fun photo ops scattered throughout the decked-out space.
Get your tickets for admission and activities in advance.
Happy’s at the Chicago Athletic Association
Nov. 25 – Dec. 23, 2025
Head to the historic Chicago Athletic Association in the Loop for Happy’s Bar, their annual Christmas pop-up bar. Billed as “an over-the-top explosion of holiday cheer”, Happy’s is taking over the ground floor of the historic hotel for the fifth year. Patrons will be greeted with cozy winter cocktails and bar bites, favorite festive tunes, and lots and lots of glittering lights.
