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Pop Out to These Festive Winter Pop-Ups

Posted on December 2, 2025
Santa Baby Bar

Santa Baby Bar in Wrigleyville. (Courtesy of MCPR)

You can go to a regular ol’ bar any day. You only have a brief window to sip Grinch-green cocktails surrounded by the warmth of twinkling Christmas lights.

It’s pop-up time.

The pop-up trend is strong in Chicago, and this winter brings plenty of options. Check out these seasonal bars and experiences to get you in the merry spirit — just make sure you go in time.

Holiday Bars

  • Rudolph's Bar at Lost Never Found in Wrigleyville has the aforementioned Grinch-green cocktails. It opens Thursday and runs till Jan. 4. Admission costs $18 and includes one drink ticket.
  • Santa Baby Bar, now in its seventh year, runs at Stolen Saddle at Wrigleyville till Jan. 4. It also costs $18 and includes one drink ticket.
  • Christmas Club is a free option in Wrigleyville that runs till early January.
  • Zoe’s Patio in Garfield Ridge launches its Christmas pop-up on Friday.
  • Happy's Holiday Pop-Up Bar returns for a farewell season at the Chicago Athletic Association Thursday and runs till Jan. 16. It’s free to attend.
  • Holly Jolly Christmas Bar at Puttery in the West Loop runs till Dec. 28. Admission is $24 and comes with a complimentary drink.
  • Frosty’s in Goose Island and the Nutcracker Pop-Up in River North are both free to attend, but reservations are required. They run till Dec. 30.
  • 8 Crazy Nights, Chicago's only Hanukkah-themed pop-up, is on at The Graystone Tavern in Wrigleyville, but don't worry — you have more than eight nights to make it there. The pop up runs till Jan. 4.

Meanwhile, some permanent bars and restaurants have launched their own winter wonderlands. Among them: Smoke Daddy BBQ in Wrigleyville, Guinness Open Gate Brewery in West Loop, Three Dots and a Dash in River North.

Butch McGuire’s in the Gold Coast and Chief O’Neill’s in Avondale are also both famous for their Christmas decor. (Personally, Chief O’Neill’s is my favorite — I like the shepherd’s pie.)

Curling

Curling at the Gwen Hotel. (Photo credit: Gene Yoon)

Seasonal Experiences

📲 Follow along for holiday events!

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