It’s officially the holiday season and there are plenty of festive ways to celebrate. Whether you want to marvel at dazzling Christmas lights or catch a joyful Christmas concert, there’s no shortage of events and activities. One of our favorite things to do this season, though, is checking out the myriad of holiday pop-ups. From Christkindlmarket to a bar inspired by Mariah Carey, here are the best holiday experiences to hit up before they’re gone in a few short weeks.
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Christkindlmarket
It needs little introduction, but the iconic German-inspired holiday market at Daley Plaza is an annual must-visit. Guests can browse stalls stocked with handmade gifts and ornaments; enjoy German fare like raclette sandwiches, brats and potato pancakes; and imbibe plenty of hot beverages that keep them warm as they wander around and soak in the festive atmosphere. Don't leave without trying spiced glühwein, a German hot wine concoction that's served in the market's famous boot mugs. First-timer? Consult our guide on what to eat, drink and do at Christkindlmarket.
Mariah Carey's Black Irish Holiday Bar
It’s only fitting that the Queen of Christmas would have her own holiday pop-up bar. Set inside the Virgin Hotels Chicago, Black Irish by Mariah Carey lets guests recreate the iconic cover photo from Mariah Carey's Magical Christmas Special, write letters to Carey herself and sip cocktails made with Black Irish, the Irish cream liqueur inspired by the singer’s heritage. Oh, and you’ll hear “All I Want For Christmas Is You” for the hundredth time, of course.
Santa Baby Bar
Tropical bar Bamboo Bar gives itself a massive makeover during the holiday season, transforming into a multi-level Christmas pop-up with wall-to-wall decor. You'll find photo-ops galore as well as drinks decked out with decorative garnishes and garlands, including large-format cocktails like the Tropical Sleigh Ride and Moët Mistletoe. Feeling hungry? Feast upon festive options like Santa's Smash Burger, Festive Fry Flight and Grinch Shake. Families are welcome during the day, but after 8pm it’s 21+ only.
Jack Frost Holiday Pop-Up
The crew behind popular fall attraction Jack’s Pumpkin Pop-Up also operates this outdoor winter wonderland in West Loop. The sprawling, two-acre pop-up boasts a Christmas market, photo opportunities and a variety of activities like ice skating, bumper cars, axe throwing, curling and more. You'll also have the opportunity to sip on boozy hot cocoa and other holiday cocktails while wandering through a light-filled Christmas tree walk.
8 Crazy Nights
Wrigleyville’s Graystone Tavern hosts Chicago’s only Hanukkah-themed pop-up bar. The interior and weatherproof patio are filled with more than 30,000 blue-and-white lights, dreidel ornaments, lighted menorah and a Hanukkah sweater wall (among other festive bits of decor). Guests can also nosh on classics such as latkes and matzo ball soup alongside not-so-traditional options like a gelt fudge sundae. Thirsty? Order the Mega Mensch Mule, a 96-ounce drink that serves 6-8 people.
Winterland at Gallagher Way
Although there won’t be any attractions inside Wrigley Field this year due to the NHL Winter Classic, Winterland at Gallagher Way returns for another go-round. Taking place outside the ballpark, the pop-up features a variety of seasonal activities, including photos with Santa, a winter market, carnival rides and holiday movie screenings on select Thursdays throughout December.
Holiday Honky Tonk at Big Star Wrigleyville
Inspired by 2024’s breakout star—Chappell Roan—and her hit song “Pink Pony Club,” Big Star has turned its Wrigleyville outpost into a holiday honky tonk pop-up. Enjoy limited-time items like Smokey Brisket Nachos and Cowboy Coffee while jamming out to Christmas tunes combined with modern country-infused classics. The space is glammed up for the occasion as well, boasting glittery hanging ornaments and a Christmas tree dressed up in pink cowboy hats.