Chicago has no shortage of pop-up bars and experiences to get you into the holiday spirit — and keep you warm with some festive drinks. Here are the spots on our holiday bucket list.
Best for Nostalgia: Happy’s Holiday Bar
🗓️ Through Dec. 22
Not only is the Chicago Athletic Association’s lobby decked out in twinkling lights, but the Loop pop-up is serving festive cocktails, dry-aged beef chili, and Chicago mix popcorn.
Easiest Free Shot: Ms. Claus and Ms. Claus
🗓️ Through Dec. 23
Dorothy will host a sing-along to “The Muppet Christmas Carol” and serve mocktails and cocktails. Want a free shot? Donate a Ms. Claus decoration to the lesbian cocktail lounge in Ukrainian Village.
Best for Hanukkah Fun: 8 Crazy Nights
🗓️ Through Jan. 7
The Graystone Tavern in Lakeview has been transformed with dreidel ornaments, menorah decor, and blue-and-white lights. Order dishes like latkes and matzo ball soup.
Best for Jingle Bells: Brando’s Lincoln Park
🗓️ Through Jan. 7
Pull up to the North Side karaoke bar to sing holiday tunes at the “Mean Girls”–inspired winter talent show, participate in ugly sweater contests, and even meet Santa.
Krampus, featured on the left in this vintage postcard, will be celebrated at an Avondale bar. (riptheskull / Flickr)
More Naughty Than Nice: Krampus
🗓️ Dec. 1–29
Avondale will see the return of Krampus, the creature who scares misbehaving children during the holidays, at DMen Tap with a parade, a kids dungeon crawl, and more.
Best for Kids:
Winter Wonderland Party
🗓️ Dec. 16
Kids can go to 115 Bourbon Street in Merrionette Park for the one-day fest featuring crafts, airbrush tattoos, dancing, a buffet, and more.
Best for No Reservations or Cover:
Reindeer Room
🗓️ Through the holidays
Tack Room, Thalia Hall’s piano bar in Pilsen, has all the cozy vibes, tunes, and cocktails for the holiday season.
Best Variety:
The Promontory
🗓️ Through the holidays
The Hyde Park venue is hosting everything from a winter farmers market to an arts fest to an ugly sweater party over the next month.
