eATLAS’ Guide to Chicago’s 2025 Holiday Pop-Ups

Any discussion of holiday pop-ups in Chicago begins with the Christkindlmarket, which has been in Daley Plaza since 1996. Based on Germany’s outdoor winter markets, the Christkindlmarket is packed with stalls selling gifts from all over the world, plus traditional German food and drink, with hot chocolate, cider, and spiced wine served in a collectible souvenir mug. 

By Dave Lifton (@daveeatschicago)

Smaller – and less crowded – versions of the Christkindlmarket are located in Aurora’s RiverEdge Park and Wrigley Field’s Gallagher Way. The stadium is also the site of Winterland, with a skating rink, holiday train running through Wrigley’s concourse, weekend visits from Santa, movie nights, and wreath workshops. 

Wrigleyville remains the epicenter of Chicago’s Christmas cheer, with 28 bars temporarily rebranded with names like Elf’d Up (Stretch), Happy Alcoholidays (Happy Camper), and Candy Cane Lane (Rizzo’s Bar and Inn), plus Graystone Tavern’s annual transformation into the Hanukkah-themed 8 Crazy Nights. All feature over-the-top décor, festive cocktails, and plenty of holiday cheer.

The merriment of Wrigleyville is condensed into Jack Frost, where an empty lot in Fulton Market is decked out with 1 million lights, displays for photo ops, and a Christmas chalet. While there, enjoy ice skating, winter bumper cars, curling, axe-throwing, and plenty of drinks. 

But 1 million lights aren’t enough for some people. Thankfully, the annual ZooLights is for them. See the Lincoln Park Zoo decked out with 3 million lights, including the Zooltide light show on the South Lawn. While there, ride the carousel and Ferris wheel, grab a hot drink or roast s’mores on an open fire, and check out a live ice sculpture carving on weekends. 

Dazzling lights are also on display at two suburban institutions. Lightscape at the Chicago Botanic Garden is a 1.3-mile stroll through a series of displays created by artists from around the world. The Winter Cathedral (pictured below) returns from previous years, but the rest of the path is new to the garden. Morton Arboretum’s Illumination projects lights onto its trees with a soundtrack created to enhance the experience. A private igloo can be rented for groups of up to 10 people, with a package that includes non-alcoholic beverages, s’mores and other holiday snacks.

If the winter weather makes you long for a Polynesian vacation, visit River North Pole at Three Dots and a Dash, Chicago’s famous Tiki bar. The mixology team has put wintry spins on their tropical cocktail menu, including a Gingerbread Painkiller, Cranberry Mai Tai, and Eggnog Grasshopper. Groups of up to six people can also enjoy concoctions served in a giant Santa’s head or elf’s uniform. 

Navy Pier, typically associated with summertime in Chicago, has plenty of family-friendly fun for the season. Check out the Winter Wonderfest, where you can go for a spin on the 200-foot Centennial Wheel, ride the kiddie train and, for taller people, the Cliffhanger and bumper cars. Harry Caray’s Tavern has transformed into the Lakefront Lodge – private rooms decorated like winter cabins for group events – with add-ons like a hot chocolate bar, private whiskey tasting, or 90-minute curling session. And every Saturday at 8PM is the pier’s famous fireworks display. 

The inaugural Holidays @ Skydeck at the Willis Tower allows you to celebrate the season from 1,353 feet above the city. In addition to having its lower-level museum and observation deck outfitted with lights and giant ornaments, they’ve planned special events on certain days, including carolers and other musicians, a holiday market, and a performance of The Nutcracker by Ballet 5:8. 

Lower to the ground than the Skydeck, but still pretty high, is Rudolph’s Rooftop Winter Igloos at the LondonHouse Hotel. Reserve a heated igloo for up to six people and select food and drinks from a seasonal menu while enjoying a view of the city’s majestic skyline from its heart overlooking the Chicago River. 

For the fourth year, you can have A Very Dandy Holiday at River West’s The Dandy Crown. Known for its craft cocktails, the bar gets whimsical for the season with drinks like Grandpa’s Pocket (Werther’s infused bourbon, vanilla, demerara, orange) and Me, I Want a Hula Hoop (gin, lemon, raspberry white chocolate syrup, prosecco). Enjoy them on the heated outdoor patio. 

The Everything Bar in West Town is celebrating an Emo Christmas, with six drinks named in honor of the punk-but-gloomy musical genre from the early ‘00s, plus DJs, trivia and karaoke on select nights  Buying a ticket for a 90-minute reservation comes with a welcome drink. 

Lastly, the Winer Wonderland at JoJo’s Shake Bar in River North features boozy and non-alcoholic milkshakes and hot chocolates for decadent, drinkable desserts. JoJo’s is also offering daily ornament painting activities, as well as mixology classes and gingerbread house decorating nights.  

Reservations or advance tickets may be encouraged or required for some attractions. Check the official websites for full details.