What are the best holiday pop-up bars in Chicago for a festive date night?

Let’s face it, the holiday season can be stressful for parents. You’re trying to see holiday attractions, you’re buying gifts for everyone and hopefully fitting in some self-care. While making your list (and checking it twice), set some time aside and enjoy a jolly cocktail at these holiday-themed bars in Chicagoland.

Updated Dec. 7, 2025: This article was reviewed and updated by the Chicago Parent editorial team to reflect new event dates, refreshed links and the latest information available for families.

Holiday Pop Up Bars in Chicago 

The Christmas Club

• Address: 3462 N. Clark St., Chicago
• Cover: None
• Kids allowed: Weeknights before 7 p.m.; Weekends before 5 p.m.

Known as the original Christmas pop-up, The Christmas Club is certainly worth the stop if you’re doing a holiday bar crawl in Wrigleyville. You’ll enjoy two floors of Christmas decorations, visits from Santa and other holiday characters. Don’t forget about their special drinks — we recommend Cousin Eddie’s Old Fashioned in a souvenir mug.

Elf’d Up

• Address: 3485 N. Clark St., Chicago
• Cover: None
• Kids allowed: Monday-Thursday before 6 p.m.; Friday-Sunday before 2 p.m.

If you’re like me and have watched “Elf” a million times at home, you know Buddy the Elf knows how to spread Christmas cheer. This pop-up bar is centered on the energized elf—and you can expect to see Buddy on Thursdays-Sundays! They’re even serving Buddy’s Breakfast Pasta with pasta, maple syrup and all the sweets you can imagine.

Frosty’s A Christmas Bar

• Address: 809 W. Evergreen Ave., Chicago
• Cover: $26+, includes one drink

Frosty’s knows how to deck the halls with three floors of Christmas decorations that cover every nook and cranny. The Instagram-worthy decorations certainly make the experience worth it. While you are there, enjoy special cocktails, singing Santa shows and visits from Santa’s friends. Tip: Visit during off-peak times to avoid large crowds.

Nutcracker Christmas Pop-Up Bar

 

View this post on Instagram

 

A post shared by Things To Do In Chicago (@thingstodoinchicago)

• Address: 203 N Wabash Ave., second floor, Chicago 
• Cover: $20+, includes one drink 
• Kids allowed: No

Step into a dazzling holiday fantasy at the Nutcracker Christmas Pop-Up Bar, a tinsel covered winter wonderland complete with sparking lights and life-sized Nutcrackers. Indulge in an exclusive menu of creatively themed cocktails designed to bring festive cheer to every sip.

The Reindeer Room

• Address: Tack Room, 1807 S. Allport St., Chicago
• Cover: No

If you’re looking for something a little more classy for Christmas, stop by The Reindeer Room. This intimate piano bar is decked out for the holidays. Enjoy specialty cocktails and live Christmas music on the piano.

River North Pole

• Address: Three Dots and a Dash, 435 N Clark St., Chicago
• Cover: Free, but reservations are recommended
• Kids allowed: No

How’d ya like to spend Christmas on Christmas Island? That’s the vibe at River North Pole, an incredible tiki bar that is adding a tropical twist to your holiday date night. The Mistletoe Mai Tai is our favorite, but the Eggnog Grasshopper is a close second.

Santa Baby

• Address: 3505 N. Clark St., Chicago,
• Cover: $18.20+, reserve tickets online; VIP, $28.70
• Kids allowed: before 8 p.m.

Here’s another pop-up that feels like Christmas threw up all over (and that’s not a bad thing). Santa Baby has weekly specials to make your experience even more magical including holiday-themed trivia on Mondays and Movie Bingo on Tuesdays.

8 Crazy Nights

• Address: 3441 N. Sheffield Ave., Chicago

Graystone Tavern is celebrating Hannukah with thousands of blue and white lights, lighted menorah decor, Mensch on a Bench and more. Sip on specialty cocktails and fill up on Jewish dishes including delicious latkes and vodka-infused jelly doughnuts.

Follow Chicago Parent on Instagram.