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Food & Drink Things To Do

10 Holiday Pop-Ups In Chicago Where You Can Still Get Your Fill Of Festive Fun

By Elliot McGowan

10 Holiday Pop-Ups In Chicago Where You Can Still Get Your Fill Of Festive Fun

Christmas is close—and that means cozy holiday-themed pop-ups have taken over!

As the holiday season approaches its most climactic day we’ve decided to put together a list of some of the most festive holiday-themed pop-ups and bar revamps around Chicago. Each year various bars and restaurants transform their spaces and this year they have adapted to the hurdles of 2020 and gone all out in holiday spirit offering us bedecked patios, festive rooftops, and magical outdoor winter wonderlands.

Whether you’re looking to enjoy some holiday cheer this season, trying to find the next venue for your holiday party, or just want to check out a new space, here are 10 holiday pop-ups and revamped bars to get your fill of festive fun!

1. Santa Baby Pop Up At Deuce’s

Wrigleyville’s immersive Christmas pop-up, Santa Baby,  has once again taken over Deuce’s Major League Bar covering a revamped patio head-to-toe and wall-to-wall with an exorbitant amount of Christmas decorations. The Santa Baby Pop-Up offers an impressive array of extraordinary drinks and some exquisite snacks. Mega-Merry-Milkshakes like the “Red Velvet Cakeshake” and extravagant Christmas cocktails like the Elf Fashioned and Jingle Juice as well as a selection of the best holiday beers comprise an unparalleled drinks menu with something for everyone.

The food is equally as enticing with “Atomic Yule Logs” consisting of three cheese sticks covered in Flamin’ Hot Cheetoh crust and Sriracha dust while the  “Christmas Dinner Sliders” consist of turkey burger sliders topped with cranberry mustard and come with marshmallow creme-covered sweet potato fries. The decorations, drinks, and food make this a number one Chicago holiday pop up.

Where: 3505 N Clark Street, Chicago
Dates: December 3 – January 6

2. Blitzen’s Holiday Pop Up At Recess

After opening last year Recess in Fulton Market has been an iconic Chicago hideout. Home to a 14,500 -square-foot patio nestled within a ring of over 30 shipping containers, it’s a spot you won’t forget. The cozy den is filled with bars, food stands, and bonfire tables but it’s offering even more for the holiday season. A special event by the name of Blitzen’s: A Holiday Pop Up offers a West Loop winter wonderland that merges art, festive fun, and lots of Christmas-themed cocktails.

The toasty hideout is brimming with Christmas magic. 6 festive photo ops offer the perfect place to capture those final Christmas moments and the 12 Drinks of Blitzen guarantee you’ll have some exquisite themed cocktails to get through. Each ticket to Blitzen’s Holiday Pop Up comes with a Blitzen cocktail, a Recess Peanut Butter Cup spiked hot chocolate, S’mores, and a DIY cookie decorating kit. There is also a Letters To Santa station where children can send their holiday wish lists straight to Santa in the North Pole.

Where: 838 W Kinzie Street, Chicago
Dates: December 3 – December 20

3. Jack Frost Winter Village On Goose Island

Jack Frost Winter Village spans a 2-ace field in the historic Goose Island offering a 100% outdoor Christmas extravaganza from the same team who gave us Jack’s Pumpkin Patch in fall. This time the field has been kitted out with over a million twinkling lights and hundreds of sprawling evergreen trees creating an exhilarating Christmas tree trail.

There are also fantastic photo opportunities and seasonal scenes so you can grab those memorable Instagram moments. As the largest, and only, evergreen Christmas tree trail in downtown Chicago, Jack Frost Winter Village provides the perfect family trip out.

Where: 1267 W Le Moyne Street, Chicago
Dates: November 24 – January 10

4. Rudolph’s Rooftop At London House Chicago

From the fields of Goose Island to the rooftops of Michigan Avenue, London House Chicago offers an unforgettable holiday experience up in the clouds. The luxury lifestyle hotel has launched its first-ever Rudolph’s Rooftop. Whimsical décor, rentable outdoor igloos, and celebratory cocktails served from the hotel’s iconic ice bar offer a holiday experience that shouldn’t be missed. Heaters and blankets mean you can enjoy breathtaking panoramic views of Chicago while staying warm and cozy.

Where: 85 East Wacker Drive, Chicago
Dates: November 5 – January 3

5. 8 Crazy Nights At The Graystone Tavern

It’s not just Christmas-themed pop-ups you’ll find in Chicago. Back by popular demand, The Graystone Tavern has resurrected its 8 Crazy Nights: A Hanukkah Bar for 2020. The bright blue bar has emerged from the swarms of red and green with the objective of giving Wrigleyville’s festive season a vibrant new identity. The bar is commemorating the Jewish holiday in its spacious and enclosed new weatherproof patio with over 8,000 blue and white lights and Hanukkah ball lanterns hanging from the ceiling.

The food menu includes favorites like Latkes, Matzo Ball Soup, Brisket Platter, as well as decadent Boozy Jelly Donuts made with housemade vodka-infused jelly. Make sure to order the 18-foot giant menorah “shotski,” starting at $24, so all your friends can take a shot at once. There will also be a photo booth with Hanukkah Props where you can mark your crazy night out with hilarious snapshots.

Where: 3441 N Sheffield Avenue, Chicago
Dates: November 20 – January 3

6. Winter Wonderland At The Godfrey Hotel

Another high up holiday pop up can be found over at The Godfrey Hotel. The annual winter wonderland event on the Godfrey Hotel’s indoor-outdoor rooftop has returned for its fifth year. The hotel lounge’s large fourth-floor terrace has been transformed into an astounding outdoor oasis. Guests can cozy up in one of the many heated, clear-domes igloos on the rooftop terrace or rent an extra-large igloo for a special winter wonderland experience. Outdoor firepits, patio heaters, s’mores, Christmas cocktails, and sensational views of the Chicago skyline offer a truly magical way to celebrate the season.

Where: 127 West Huron Street, Chicago
Dates: November 1 – January 31

7. Rudolph’s Bar At Casey Moran’s

If there is one neighborhood you can rely on for seasonal spirit and Christmas pop-ups it’s Wrigleyville. This time of the year, it looks more like a tiny arctic Christmas village than the home of the Cubs baseball team. The creators of the Santa Baby Pop Up are also the team behind Rudolph’s Bar just down the road. Casey Moran’s beer garden features a retractable roof and outdoor heaters making it the perfect spot to host a Christmas pop-up with the circumstances of 2020. You can expect more interactive over-the-top Christmas decor here, some sensational drinks like the Mr.Grinch, as well as more of the fantastic food.

Where: 3660 N Clark Street, Chicago
Dates: November 23 – December 31

8. Winter Wonderland At Jo Jo’s Shake Bar

Another place you can rely on for a magical seasonal pop up is JoJo’s Shake Bar. Following the success of their autumnal Pumpkin Patch Pop Up, JoJo’s Shake Bar is now hosting an outdoor winter wonderland. In a 5,000-square-foot outdoor space in River North, the incredible food and beverage experience is a food fanatic’s Christmas paradise. Cookie flights, spiked ciders, biggie hot chocolates, and The Winter Wonderland Shake are just a few of the sublime options down at JoJo’s Winter Wonderland.

Where: 23 West Hubbard Street, Chicago
Dates: November 13 – December 31

9. A Holly Jolly Pop Up At Roosevelt Collection Shops

A Holly Jolly Christmas Popup is a collection of 13 holiday-inspired art installations crafted to delight both the young and the young at heart. The pop up offers an ideal social distance-friendly way to take holiday pics with family or friends. Guests can roam around a series of sets with dazzling lights, jolly sounds, and comforting scents of the holiday season including “Santa’s Candy Land” and “Greeetings from Snowmanland”. There will be an appearance from the big man himself in a pop up that offers Chicago’s best place for those holiday snaps and Instagram shots.

Where: 11143 S Delano Ct, Chicago
Dates: December 1 – December 24

10. Gingerbread Houses At Whiskey Business

Whiskey Business is also now home to some of the cutest little gingerbread houses. The bar’s rooftop cabanas have been converted into heated gingerbread houses that you can rent with a group of friends and live out your own private fairytale experience in the heart of Chicago.

Up on Whiskey Business’s Wicker Park rooftop, little heated cabanas have been turned into cute gingerbread houses that you can rent with friends or family. The private hideouts have been decked out with fake fireplaces, candy canes, and Christmas decorations so you can sink a few seasonal cocktails surrounded by festive cheer. Whiskey Business’s “gingerbread house contest” also invites you to build a gingerbread house within their gingerbread houses. Friends or families who feel they’ve made something special can then post their self-made gingerbread houses to Instagram to be in with the chance of winning a weekly $50 gift card!

Where: 1367 N Milwaukee Avenue, Chicago
Dates: November 13 – February 27

See more: 15 Of The Coziest Outdoor Dining Options In Chicago