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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.

Paradise Park Pizza

We all know Paradise Park is one of the best places in the city to grab a slice, but it’s also one of the best spots to get into the holiday spirit with its merry decor, lights, and seasonal menu items. Gather the group and go out for pizza and a festive cocktail surrounded by a dazzling display of holiday cheer.

Where: 1913 W. North Ave., Chicago, IL 60622
For more information on Paradise Park Pizza.


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Bad Santa Party

The Loft Nightclub gets naughty Saturday, December 17, for its first annual Bad Santa Party. Come dressed in your best themed attire for a shot at winning the a $500 cash prize. Take a picture with Bad Santa, and enjoy holiday-themed drinks and festive mashups from a live DJ! The party goes until 3 AM, and tickets include an open bar from 9 PM–11 PM, Christmas shots and themed drinks, and Santa hats!

When: December 17
Where: The Loft: 2251 N Lincoln Ave, Chicago, IL 60614

For more information on Bad Santa Party.

DIY Christmas Cookie Decorating & Cocktails at Millennium Hall

Decorate handmade Christmas cookies while sipping festive cocktails at Millennium Hall’s Holiday Pop-Up (located inside Millennium Park). Learn to make two holiday-themed cocktails, then sip on them as you decorate freshly-baked cookies with colorful frosting and decorative toppings.

The space will be decked out in tinsel, trimmings, ornaments, and more, allowing you to immerse yourself in the holiday magic! A la carte food and beverages are available for additional purchase at the restaurant.

Where: Millennium Hall: 11 N Michigan Ave, Chicago, IL 60602
For more information on DIY Christmas Cookie Decorating & Cocktails.

Butch McGuire’s

The family-owned Irish saloon in Near Northside is a staple Chicago bar and restaurant all year-round but is definitely worth a visit during the holiday season. For over 50 years, tinsel, garlands, ornaments, and lights have been hung from the ceiling, around the windows, and from the bar to create an explosion of holiday cheer from the moment guests step foot into the longstanding establishment.

Most notable though is the Butch McGuire Holiday Express. Every train you see running above your head at Butch McGuire’s is sponsored with generous donations to Chicago Mercy Home For Boys and Girls.

Where: 20 W Division St, Chicago, IL 60610
For more information on Butch McGuire’s.

Gingerbread House Making & Cocktails at the Pink Squirrel

Get into the holiday spirit with a gingerbread house-making experience in Tinseltown at the Pink Squirrel, Logan Square’s best holiday pop-up bar. Immerse yourself in a winter wonderland, decorated from top to bottom in over-the-top holiday decor as you create a gingerbread masterpiece. Cocktails and shots are included with each ticket!

Where: Tinseltown Holiday Bar (The Pink Squirrel): 2414 N Milwaukee Ave, Chicago, IL 60647
For more information on Gingerbread House Making & Cocktails at the Pink Squirrel.

TBOX Holiday Bar Crawl

What started as a bar crawl at 12 bars (Twelve Bars of Christmas, aka TBOX) is now the world’s largest, longest-running, and most spectacular holiday bar crawl taking place at tons of bars in the Wrigleyville neighborhood! Whether you're naughty or nice, it's time to get into the holiday spirit at this iconic Chicago event. Tickets include admission to all bars and free breakfast buffets, gift cards to use on the crawl, drink specials, giveaways, and more!

Where: Wristband pick-up: TBA
For more information on TBOX.

Merry Little Christmas

Have a Merry Little Christmas while sipping seasonal cocktails at Millennium Hall’s Holiday Pop-Up inside Millennium Park. Expect to be immersed in tinsel, trimmings, and ornaments while enjoying a la carte food and beverage options and a full menu from the restaurant (including authentic Neopolitan pizza). Pro-tip: Book Ice skating at the rink next door to round out a perfect evening of holiday festivities!

Where: 11 N Michigan Ave, Chicago, IL 60602
For more information on Merry Little Christmas.

Boozy Holiday Igloo

Is anything more festive than sipping a cup of hot chocolate inside a cozy, giant igloo? The Boozy Holiday Igloo is a light-up oversized heated igloo on the rooftop of Whiskey Business in Wicker Park. Enjoy plenty of fun games like giant connect four and Jenga, cozy lounge spaces, and boozy and non-boozy hot drinks.

Where: Whiskey Business: 1367 N Milwaukee Ave, Chicago, IL 60622
For more information on Boozy Holiday Igloo.

JoJo’s ShakeBAR’s Winter Wonderland

Check out JoJo's immersive dining experience for good times and seasonal fare. Step into a Winter Wonderland and rock around the 17-foot Christmas tree to your favorite holiday tunes, or cozy up with a Biggie Hot Chocolate and friends in one of JoJo’s private igloos.

The festive (and heated) patio setting is the perfect place to escape the cold and enjoy JoJo’s decadent milkshakes, holiday cocktails, and delicious diner fare. Come hungry and enjoy the Honey Fried Chicken Sandwich, Smash Burger, loaded Fries, or the belly-warming chicken pot pie!

Where: River North: 23 W Hubbard St, Chicago, IL, 60654
For more information on JoJo’s ShakeBAR’s Winter Wonderland.

Jack Frost Winter Fest

Jack Frost Winter Fest has it all—ice skating, snow tubing, holiday photo ops, full bars, axe throwing, millions of holiday lights, and a Christmas tree farm! Round up your friends and family and pack in as much festive wintertime fun as possible. Tickets include one Christmas cocktail, two snow tube rides, and three ace throws.

Where: 1265 W Le Moyne St, Chicago, IL 60642
For more information on Jack Frost Winter Fest.

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 on Chestnut Street. Each ticket includes one complimentary cocktail, a Santa hat, and a Christmas bulb necklace.

Where: 100 E Chestnut St, Chicago, IL 60611
For more information on the Nutcracker Christmas Pop-Up Bar & Hotel.

Holly Jolly Pop-Up Bar at Electric Garden

Do you miss the wonder of the holidays when you were a kid? Stepping into the Holly Jolly Holiday Bar will bring a little bit of the magic back. Electric Garden will be decked top to bottom in Christmas-themed decor, so grab tickets and go enjoy a festive cocktail, photo ops, and a little magic.

Where: Electric Garden: 324 S Racine Ave, Chicago, IL 60607
For more information on the Holly Jolly Pop-Up Bar.