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 Christmas bars in Chicago to get your fill of festive fun!
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 its yearly autumnal Pumpkin Patch Pop-Up, JoJo’s Shake Bar is back on November 15 to host its annual winter wonderland pop-up.
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 the exclusive Winter Wonderland Shake are just a few of the sublime options down at JoJo’s Shake Bar.
Address: 23 W Hubbard St, Chicago, IL 60654
Dates: November 15 – January 5
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 beginning November 16.
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 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
Dates: November 16 – January 31
Winterland at Navy Pier
Step into this joyful Winterland experience this holiday season at Chicago’s Navy Pier. The festive winter wonderland is only open for a limited time, from November 22, 2024, until January 5, 2025, featuring high-tech projections and mesmerizing lighting effects surrounded by the joy of Christmas at every turn. Families will love the snow globe, an ideal spot for holiday photos, a Polar Express-themed train, towering Nutcrackers, and much more! Get your tickets now!
Address: Navy Pier, 600 E. Grand Ave., Chicago, IL, USA, 60611
Dates: November 22 – January 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 2024.
The bright blue Chicago holiday pop-up will return on November 27, commemorating the Jewish holiday in its spacious weatherproof beer garden and interior 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.
Festive cocktails include the Gelt Martini, Hebrew Cold Brew, Hanukkah Harry’s Hot Chocolate, Rockin’ Rabbi, and more.
Dates: November 27 – January 5
Address: 3441 N Sheffield Ave, Chicago, IL 60657
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.
Elf’d Up will feature 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 5th, head on over before Buddy moves out.
Address: 3485 N Clark St, Chicago, IL 60657
Dates: November 9 – January 5
Winter Wonderland at The Godfrey Hotel
Another fantastic holiday Chicago pop-up is coming to The Godfrey Hotel on November 23!
The annual Winter Wonderland pop-up 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-domed 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
Dates: November 23 – February 12
A Very Dandy Holiday at the Dandy Crown
A Very Dandy Holiday is back again this holiday season at The Dandy Crown in River West!
From now through January 4, 2025, guests can head to The Dandy Crown for holiday-themed craft cocktails and mocktails, visits with Santa, holiday trivia, and several themed Christmas parties.
Admission to A Very Dandy Holiday is free to all!
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 on November 22, 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
Dates: November 22 – early January 2025
Jack Frost Winter Fest
The annual Jack Frost Winter Village is back in Fulton Market beginning November 29 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
Dates: November 29 – January 5
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
Dates: November 15—early January 2025
Noche Buena
This festive season, Moe’s Cantina in Wrigleyville has transformed into a “Navidad” wonderland with the launch of Noche Buena Christmas Bar.
The one-of-a-kind pop up combines Latin holiday traditions, flavors, and music for a one-of-a-kind holiday experience.
Guests can savor treats like Puerto Rican Eggnog or “Coquito”, Mexican Ponche, Tamales, and more, all while socializing in the ambiance of the elaborately decorated space.
Noche Buena is the perfect opportunity to enjoy some festive fun while immersing oneself in Hispanic heritage. Holiday attire is recommended!
Address: 3518 N Clark St, Chicago, IL 60657
Dates: Now through January 6, 2025
Winter Wonderland at Rainbow Cone in Wicker Park
What’s better than a holiday pop-up? How about a holiday pop-up with ice cream on top?
This Christmas season, Rainbow Cone in Wicker Park is transforming into a winter wonderland, complete with sparkling pink Christmas trees, disco balls, and holiday decorations galore.
Guests can enjoy seasonal peppermint treats like creamy shakes and signature peppermint sliced cones. Guests will also enjoy some family-friendly activities and plenty of festive photo ops.
The pop-up is open now through January 4, be sure to stop by and treat yourself this holiday season!
Address: 1750 W Division St, Chicago, IL 60622
Dates: Now through January 4, 2025
Christmas Island Holiday Pop-Up at Margaritaville Chicago
Margaritaville at Navy Pier is bringing the tropics to the Windy City this festive season with its Christmas Island Holiday Pop-Up.
From now through January 5, Margaritaville will be decked out in Christmas décor and serving up some delicious holiday cocktails.
Guests can sip on the passionfruit tequila-infused Sleigh Ride cocktail or the festive Kringle & Coke with crème de menthe and spiced rum.
Chicagoans can stop by any time during normal business hours.
Address: 700 E Grand Ave #118, Chicago, IL 60611
Dates: Through January 3, 2025
Holiday Honky Tonk at Wrigleyville’s Big Star
Big Star in Wrigleyville is having a first-ever Holiday Honky Tonk pop-up! One of the newest Christmas bars in Chicago, the Holiday Honky Tonk is inspired by Chappell Roan’s “Pink Pony Club,” and the Big Star crew is going full glam for the season! They’ll be decking their halls with glittery hanging ornaments, a Christmas tree dressed up in pink cowboy hats, and, of course, a new lineup of food & drink specials.
The pop-up will also expand on its regular catalog of cowboy classics with a heavy emphasis on Christmas tunes combined with current modern country hits.
Address: 3640 N Clark St, Chicago, IL 60613
Dates: November 27—January 1