Celebrate the holiday season with Chicago’s best festive pop ups

With the holiday season around the corner, festive pop-ups are making a comeback around Chicago. Each exciting event brings family-friendly activities, festive photo ops, seasonal food and drinks, elaborate decorative displays, and so much more. Check out our holiday pop-up roundup to find the perfect event for all your merry making needs.

Jack Frost Winterfest pop up

Prepare to be enchanted by Fulton Market’s newest holiday attraction, the Jack Frost Chirstmas Holiday Pop-Up. Created by some of Chicago’s greatest minds in event planning, the Jack Frost pop-up is sure to make this Christmas season one you’ll never forget.

Enjoy family-friendly activities like ice skating and bumper car rides, or find the perfect gift with the ultimate Christmas market shopping experience. Sample festive treats like boozy hot cocoa and signature cocktails.

Activities like Ax throwing and ice curling promise to bring a fun and competitive edge to your holiday outing. The pop-up will also feature plenty of fun photo ops and other exciting activities.

Tickets for the Jack Frost pop-up are expected to go quick, so be sure to secure your spot ahead of time.

Frosty's pop up

Frosty’s, Chicago’s original Christmas pop-up bar, is back for its seventh year from November through January. Frosty’s features four bars, three levels, and two dance floors, making it a one-stop destination for your holiday festivities. Try special seasonal cocktails like The Very Merry Punch and Baby it’s Cold Outside Martini. Celebrate with elaborate holiday decorations including life size Nutcrackers and enjoy non-stop holiday music.

Frosty’s will run from November 18, through January 5, 2024. Visit Frosty's official website for ticket options and stay up to date by checking out their social media.

Third coast hospitality group pop ups

Third Coast Hospitality Group is bringing holiday cheer to Moe's Cantina-Wrigleyville and Old Crow Smokehouse with themed pop-up events from November 22 through January. Two unique experiences, Santa's Workshop and Grinch Stole Christmas, will offer festive cocktails, seasonal food, decorations, and appearances by holiday characters.

Moe’s Cantina Wrigleyville and River North

Moe's Wrigleyville and River North have transformed into a Grinch-themed holiday pop-up, featuring festive decorations, a special menu with items like birria tacos and buñelos, and a selection of fun holiday drinks. Guests can meet various Grinches, including a live character, and encounter familiar faces from Whoville, making it a lively and immersive holiday experience.

Old Crow Smokehouse

Santa Claus is coming to Old Crow Smokehouse as the Wrigleyville barbecue spot morphs into Santa’s Workshop for the season. Giant Christmas balls, white lights and Christmas trees set the holiday scene, while the holiday menu features comfort food favorites like French Onion Soup, Old Crow Pot Pie, and Hot Honey Chicken Biscuit Sliders. Specialty cocktail options include the bright and icy Jack Frost, the nostalgic Dirty Chocolate Milk, Harry Potter’s Boozy Butterbeer, and the Polar Espresso.

Instagram-worthy photo ops include Santa Claus and his sleigh and reindeer, Ralphie from “A Christmas Story,” Buddy the Elf, and the Old Crow giant Christmas horse. 

Old Crow Smokehouse and Moe’s Cantina Wrigleyville will be open during the holiday season Thursday- Friday 5 p.m.-12 a.m. and Saturday-Sunday 11 a.m.-12 a.m. As Christmas gets closer, the venues will open their doors on additional days as well. All pop-up events welcome children until 9 p.m., and seating is first-come, first-served.

The author generated this text in part with GPT-3, OpenAI’s large-scale language-generation model. Upon generating draft language, the author reviewed, edited, and revised the language to their own liking and takes ultimate responsibility for the content of this publication.