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Published November 27, 2023

The Most Festive Holiday Bars and Pop-Ups in Chicago This Season

Make the most of the holidays in Chi-Town. 🎄🍸✨

by Chicago Bucket List


The holidays are upon us, and Chicago is showing out with tree lightings, ice rinks, holiday markets, and more. There are so many ways to enjoy the season (and we’ve listed them all out for you on our ultimate winter bucket list), but few things can induce the spirit of the season like sipping a festive drink surrounded by an impressive display of holiday decor can.

This time only comes once a year, though, so we’ve rounded up the top holiday bars and pop-ups in Chi-Town this winter to make sure you don’t miss out.

The Best Holiday Pop-Ups in Chicago

Jack Frost Christmas Pop-Up at Fulton Market

Jack Frost Winter Fest has it all—ice skating, snow tubing, holiday photo ops, full bars, axe throwing, millions of holiday lights, and winter bumper cars! Round up your friends and family and pack in as much festive wintertime fun as possible!

Where: 170 N Green St., Chicago, IL
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Frosty's: A Christmas Bar

Chicago's most festive holiday pop-up bar returns on November 18 and will be open all season long with all of the holiday cheer and shenanigans we've come to know and love. Bursting at the seams with over-the-top lights and decor, Frosty's will have life-size toy soldiers, roaming Santas and elves, and non-stop holiday music spinning across four bars, three levels, and two dance floors! And, of course, lots of specialty drinks and themed cocktails.

Where: Frosty's Christmas Bar: 809 W Evergreen Ave, Chicago, IL
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Nutcracker Christmas Pop-Up Bar & Hotel

Step into a world of timeless festive decor and classic holiday tunes at the Nutcracker Christmas Pop-Up Bar and Hotel. Enjoy Craft Christmas Cocktails, Charcuterie Boards, and endless Christmas fun at Virgin Hotels Chicago. Each ticket includes a 90-minute reservation and a holiday-themed welcome cocktail or mocktail. Additional drinks and holiday-themed bites will be available for purchase on-site. 

Where: 203 N. Wabash Ave, 2nd Floor, Chicago, IL
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Chicago's Ultimate 2023 Winter Bucket List
CTA Holiday Trains: Everything You Need to Know
The Top Holiday Markets in Chicago This Season


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