THIS WEEKEND IN CHICAGO – Holiday Popups Bring About a Festive Mood!
Ready or not, this is our last weekend before Christmas’ arrival on Thursday. If you’re looking to have some fun time for yourself before then, this weekend offers a slew of Holiday Popups sure to put you in a festive mood!
One of Chicago’s favorite holiday pop-ups is offering a high-energy holiday experience with Elf’d Up inside the Stretch Bar & Grill (3485 N. Clark St.) in the Wrigleyville neighborhood. Inspired by the 2003 movie Elf, this popup features tributes to the iconic Christmas movie with specialty themed cocktails like the Angry Elf Martini; a selection of holiday food that includes Buddy’s famous breakfast pasta; tables stocked with the four main food groups of candy, candy canes, candy corn, and syrup; and many other surprises. In addition, if you’d like to meet Buddy himself, your best bet is between Thursdays and Sundays when he’s known to make an appearance from time to time. Plus, this popup requires no cover or reservations since it’s based on a first-come, first-serve basis so you may want to visit early or on weekdays. As it’s said, it’s the best way to spread Christmas cheer singing loud for all to hear!
Another ultimate Christmas holiday experience returns to 809 West Evergreen Avenue in the Lincoln Park neighborhood with Frosty’s Christmas Bar. This popup offers three levels featuring life-size Nutcrackers, sexy Santas and Elves, non-stop holiday music as well as four bars and two dance floors for endless Christmas fun. So, don your favorite holiday attire as you enjoy seasonal cocktails, immersive holiday photo ops, and plenty of dazzling lights for the ultimate seasonal experience that’s bigger, brighter, and merrier than ever before!
A multi-level, immersive Christmas popup awaits you at the Stolen Saddle (3505 N. Clark St.) in the Wrigleyville neighborhood with their Santa Baby Christmas Bar. Once there you’ll experience wall-to-wall décor; photo ops galore; multiple bars; a full food menu with festive options like Santa’s Smash Burger, Festive Fry Flight, or a Grinch Shake; a full festive drink menu with seasonal favorites such as Spiked Peppermint Cocoa or the Clausmo, and plenty of other holiday spirits. In addition, a reservation is required and families are welcome during the day until 8:00 p.m. when it’s 21+. Remember, Santa sees you when you’re drinking so you better watch out!
Another Chicago ultimate holiday must-do is Winter Wonderland at JoJo’s Shake Bar (23 W. Hubbard St.) in the River North neighborhood. Once again, JoJo’s is complete with over-the-top décor as it transforms into a winter wonderland; offers a specialty menu with comforting seasonal favorites such as themed cocktails and shakes; and includes holiday activities such as ornament painting, Holly Jolly mixology, and photos with Santa (5 p.m.-7 p.m.). You can rely on this popup for a magical holiday experience!
Chicago’s only Hanukkah-themed popup, 8 Crazy Nights, takes over The Graystone Tavern (3441 N. Sheffield Ave.) in the Wrigleyville neighborhood through January 5, 2026. The Graystone’s interior and spacious weather-proofed beer garden is decked out with over 30,000 blue and white lights, Hanukkah ball lanterns hanging from the ceiling, dreidel ornaments, a Hanukkah sweater wall, and lighted menorah to commemorate this Jewish holiday. The menu includes classic favorites like latkes, matzo ball soup, and a brisket platter along with a not-so-classic boozy jelly donut filled with house made vodka-infused jelly. In addition to the scrumptious food and Hanukkah-themed drinks, spaces have been set aside for board games like Mitzvah Match, Schmear Build-A-Bagel card game, Jewish Guess Who? and others!
Finally, and most importantly, let’s not forget Saturday evening at 7:20 p.m. for the “Sweet Revenge Game” as the Chicago Bears host the Green Bay Packers at Soldier Field (1410 Special Olympics Dr.) in the South Loop!
Have a Wonderful Merry Christmas!!
Sue Moss and Dean’s Team Chicago
