It’s the time in Chicago when holiday markets are in full swing, and the city is sparkling with numerous magical light shows.
Whether you’re looking to enjoy some holiday cheer this season, trying to find the next venue for your holiday party, or want to check out a new space, here are our favorite holiday pop-ups and Chicago Christmas bars to get your fill of festive fun!
1. Santa Baby Pop Up at Bamboo Club
One of Wrigleyville’s favorite over-the-top Christmas Chicago bars is back again this year. Known for its over-the-top decorations, the immersive Santa Baby Pop-Up has once again taken over Bamboo Club covering the space head-to-toe and wall-to-wall with an exorbitant amount of Christmas decorations.
Guests can expect a spectacular explosion of Christmas decor and photo-ops galore alongside an equally impressive array of extraordinary themed drinks and snacks that make up a sublime Christmas menu.
Address: 3505 N Clark St, Chicago, IL 60657
2. Winter Wonderland at JoJo’s Shake Bar
Another place you can rely on for a magical holiday pop-up in Chicago is JoJo’s Shake Bar. Following the success of their yearly autumnal Pumpkin Patch Pop-Up, JoJo’s Shake Bar is back again to host an outdoor winter wonderland. Covering a 5,000-square-foot outdoor space in River North and Naperville, offering an incredible food and beverage experience is a food fanatic’s Christmas paradise.
Cookie flights, spiked ciders, towering hot chocolates, and exclusive The Winter Wonderland Shake, like the Peppermint Party Hot Chocolate: Snowflake Marshmallow, Chocolate S’more, Peppermint Pretzel, and Toasted Marshmallow are just a few of the sublime options down at JoJo’s Winter Wonderland.
Address: 23 W Hubbard St, Chicago, IL 60654
3. The Nutcracker Pop-Up
Open through December 31st, this Gold Coast pop-up is filled with festive decorations, plenty of holiday music, and endless drinks (like a Christmas cocktail flight) available at two fully stocked bars. It does become a 21 and older spot after 6 PM, but if you’re looking to enjoy a charcuterie board with the family, you can still grab a ticket and make a reservation at the decked-out bar before then.
Address: 100 E Chestnut St, Chicago, IL 60611
4. Rudolph’s Rooftop at London House Chicago
Head to a one-of-a-kind Rudolph-themed hangout up on the rooftop of London House Chicago at the second-annual ‘Rudolph’s Rooftop’ winter experience. Located on the hotel’s elegant tri-level rooftop bar, the festive holiday event is now back for a new winter wonderland experience.
Enjoy drinks and revelry on the 22nd floor at 85 East Upper Wacker Drive. In addition to some of the most unique sweeping panoramic views of Chicago’s over-the-top Christmas decor, there are also rentable outdoor igloos and holiday-themed cocktails waiting to be enjoyed.
Address: 85 E Wacker Dr, Chicago, IL 60601
5. 8 Crazy Nights at The Graystone Tavern
It’s not just Chicago Christmas bars you’ll find in Chicago. Back by popular demand, The Graystone Tavern has resurrected its 8 Crazy Nights: A Hanukkah Bar for 2023.
The bright blue bar has emerged from the swarms of red and green to give Wrigleyville’s festive season a vibrant new identity. The bar commemorates 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 menu includes favorites like Latkes, Matzo Ball Soup, Brisket Platter, and decadent Boozy Jelly Donuts made with housemade vodka-infused jelly. Order the 18-foot giant menorah “shot ski,” 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.
Address: 3441 N Sheffield Ave, Chicago, IL 60657
6. Elf’d Up
Elf fans, this one is for you! Stretch Bar & Grill is transforming its space into an Elf fan’s dream come true. The restaurant will be filled with tributes to the iconic Christmas movie, complete with complimentary cookies, themed drinks (like the Angry Elf Martini), and menu items calling back to the movie–like Buddy’s Breakfast Pasta and many more surprises. Open now through January 1st, head on over before Buddy moves out.
Address: 3485 N Clark St, Chicago, IL 60657
7. The Christmas Inn at the Hubbard Inn
The holiday season is alive and kicking, and Hubbard Inn has fully transformed into The Christmas Inn to make your holidays on Hubbard Street merry and bright! Experience 3 levels of holiday bliss with festive cocktails, Instagrammable moments, and live entertainment at this limited-time holiday pop-up!
Each floor has its own Christmas theme, with the classic magical Christmas on the first floor, 60’s ‘Kitchmas’ vibes on the second floor, and the third floor Christmas apocalypse.
From brunches and mixology classes to holiday trivia nights and paint and sip classes, there is weekly entertainment at Hubbard Inn this holiday season!
Address: 110 W Hubbard St, Chicago, IL 60654
8. Winter Wonderland at The Godfrey Hotel
Another fantastic holiday Chicago pop-up exists at The Godfrey Hotel! The annual winter wonderland event on the iconic indoor-outdoor rooftop has returned for its seventh year. The hotel lounge’s large fourth-floor terrace has been transformed for another year, turning it 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 unique winter wonderland experience. Outdoor firepits, patio heaters, s’mores, Christmas cocktails, and sensational views of the Chicago skyline offer a sensational way to celebrate the holiday season.
Address: 127 W Huron St, Chicago, IL 60654
9. The Christmas Club
Known to all as one of the original Wrigleyville Chicago Christmas bars, the annual festive holiday pop-up, the Christmas Club, is back again, taking over two floors, three party rooms, and three bars. Enjoy themed holiday cocktails and delicious snacks, along with a chance to meet Santa in person! A DJ keeps the party going with classic tunes, plus the fun bar is already open for business this season!
Address: 3460 N. Clark St., Chicago, IL
10. Jack Frost Winter Fest
The annual Jack Frost Winter Village spans a 2-ace field on the historic Goose Island. Offering a 100% outdoor Christmas extravaganza from the same team who gave us Jack’s Pumpkin Patch. This time, the field has been kitted 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 to 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.
Address: 170 N Green St, Chicago, IL, United States, 60607
11. Frosty’s Christmas Bar
Santa Claus isn’t the only one bringing the festive holiday spirit to Chicago! Frosty’s, one of the original Chicago Christmas bars, is back for its seventh year from November through January.
Featuring life-size Nutcrackers, Sexy Santas, and Elves, along with non-stop holiday music spinning until 4 a.m., this is the ultimate seasonal experience you won’t want to miss! Frosty’s Christmas Bar takes your celebration to the next level with four bars, three levels, and two dance floors. This one-stop destination is perfect for sharing the holiday spirit with friends, family, and co-workers.
Address: 809 W Evergreen Ave, Chicago, IL 60642