Christmas Club – Country Club Wrigleyville
Kimmy Collins – Aon Center
Get into the holiday spirit at Christmas Club, a holiday pop-up at Country Club. Hang out on two floors decked out in jolly decorations and listen to holiday classics all night long. Bonus – Santa and other Christmas characters even make appearances!
Reindeer Room – Tack Room
Mat Chapman – JW Marriott
Tis the season at Tack Room, which becomes Reindeer Room! Bask in seasonal decor and sip on special cocktails while listening to Tack Room’s resident pianist play merry holiday tunes and carols.
Miracle at Sable – Sable Kitchen & Bar
Mark Kraemer – Hotel Palomar
Head over to Sable Kitchen & Bar and see the Miracle at Sable – a holiday pop-up complete with festive cocktails and snacks. There is no cover, but Sable will be collecting unwrapped toys to donate to the Chicago chapter of Toys for Tots. Drink for a cause – we like the sound of that.
Callout from Alex Yu – The Peninsula
It’s really hard to beat the scale of Chicago’s annual Christkindlmarket. The spiced wine and holiday cheer warm you enough to brave the cold for schnitzels and blown-glass ornaments.
Callout from Eric Loughlin – theWit Hotel
I particularly enjoyed my time at Frosty’s which is coming back for it’s sophomore year. Don’t be fooled: this is a nightclub. However, there’s something about a whole bunch of adults in their Christmas attire absolutely bumping to “Get Low” by Lil John & the Eastside Boys that I truly had to appreciate.
Erica Abdnour, Concierge Preferred Magazine
Whether you’re looking for silly, festive, or just chill, there is an awesome place to bring in the holiday season. Check out Cousin Eddie’s at Cerise Rooftop for a Christmas Vacation-themed night that boasts 80s board games, nostalgic bites, and of course, floor-to-ceiling holiday lights. Looking for something a bit lower-key? Head to Butch McGuires to bask in the lights, garlands, and tinsel – a holiday tradition for decades at this bar loved by locals. Finally, check out Happy’s, a pop-up inside Chicago Athletic Association Hotel! There, you’ll find an explosion of holiday excitement that includes holiday cocktails, music, lights, and a list of activities that rotates throughout the duration of the pop-up – karaoke, board games, Bingo, and crafts!