This winter, Chicago raises the bar on how to toast the season. Across the city, top bars and restaurants are decking their halls with dazzling themed decor. Get ready for festive flavors and holiday spirit in every glass at a dizzying array of seasonal Christmas bars and holiday pop-ups throughout the city.
From tinsel-covered taverns to immersive experiences, the Christmas and holiday pop-up bars in Chicago are spreading cheer — one seasonal cocktail at a time.
Chicago Christmas and holiday bars
Santa Baby Christmas Bar at Stolen Saddle
Nov. 21, 2025 – Jan. 4, 2026
Go big or go ho-ho-home — this Christmas experience is anything but subtle. Santa Baby at Stolen Saddle in Lakeview features extensive decor in every inch of their space. Expect two levels of holiday magic — on the rooftop and patio — with twinkling lights, seasonal flair, and festive photo ops throughout.
Heated bars, an open-air patio, and scenic rooftop views make this a holiday dreamscape worth toasting. And the boozy holiday drinks are just as extravagant — get cocktails like the Mistletoe Mojito, Jingle Juice, Yule Mule, and spiked hot chocolate and coffee in individual and jumbo shareable sizes.
Make your reservations today.
8 Crazy Nights at The Graystone Tavern
Opens Nov. 21, 2025
8 Crazy Nights, Chicago’s first Hanukkah-themed pop-up, is returning to The Graystone Tavern in Lakeview. The space will be decorated with dreidel ornaments, lighted menorahs, a photo booth, and more than 30,000 blue and white lights.
A special food menu includes fun takes on traditional favorites like mini bagels and lox, jalapeño cheddar latkes, and brisket sloppy joes. There’s also a playful drink menu with cocktails (like the Gelt Martini), beers, and shots.
River North Pole at Three Dots and a Dash
Opens Nov. 14
One of the city’s most famous tiki bars is going polar this winter. Three Dots and a Dash is hosting a River North Pole bar takeover, turning their tropical paradise into a snowy winter wonderland with holiday decorations throughout the downtown space.
Enjoy a seasonal cocktail lineup featuring cozy hot drinks and imaginative holiday sips, all served in the same premium glassware and festive mugs as the regular menu — including a collectible snowman mug for holiday enthusiasts. Make your reservations today.
Winter Wonderland at JoJo’s Shake Bar
Now open
In River North, JoJo’s Shake Bar has launched their expansive Winter Wonderland pop-up, going all-in on holiday maximalism — expect sparkle, whimsy, and wall-to-wall holiday cheer.
Try their over-the-top holiday shakes and Santa-approved cocktails, like the giant Polar Espresso Martini and Santa’s Sangria. Plus, check out special themed events like Holly Jolly Mixology Classes and Gingerbread House Decorating. Reservations are now available.
A Very Dandy Holiday at The Dandy Crown
Nov. 21, 2025 – Jan. 4, 2026
A Very Dandy Holiday bar is back by popular demand at The Dandy Crown. Cocktails are the main draw at this West Town spot, where the award-winning bartenders will be serving up a series of themed drinks all season long.
Expect festive glassware, immersive decor, and plenty of yuletide cheer. Check the calendar for fun holiday happenings like visits from Santa, holiday trivia, ugly sweater nights, a New Year’s Eve party, and more.
Holiday Honky Tonk at Big Star Wrigleyville
Nov. 21, 2025 – Jan. 2, 2026
This sparkly holiday pop-up brings a big dose of Nashville flair to the holiday season in Chicago. This cowboy-meets-Christmas event is back and bigger than ever, transforming the popular Big Star taqueria into an over-the-top celebration of all things pink and glittery. Guests can enjoy a festive menu of seasonal cocktails, like the Rhinestone Rita, plus floor-to-ceiling decor.
Rudolph’s Rooftop Winter Igloos at LondonHouse Chicago
Nov. 22, 2025 – Jan. 25, 2026
Enjoy sweeping city views and tons of holiday cheer at Rudolph’s Rooftop. Located on the 22nd floor of the LondonHouse Chicago, this seasonal pop-up includes festive menu items, hot and cold cocktails, cozy heated igloos, holiday decor, and backdrops for capturing photos. Not to mention the stunning views of the Chicago River and the surrounding city lit up for the holidays. Contact rsvp@londonhouse.com to book your tables and private igloos.
Explore more: Keep the festive fun going at these winter rooftops and igloos in Chicago.
Jack Frost Christmas Pop-up in Fulton Market
Opens Nov. 15, 2025
From the scent of evergreens to the warmth of winter cocktails, this outdoor winter extravaganza captures the essence of the holidays. Jack Frost Christmas Pop-up in Fulton Market invites guests to enjoy ice skating, axe throwing, bumper cars, music and lights, seasonal drinks, and more. Plus, there are plenty of fun photo ops scattered throughout the decked-out space.
Happy’s at the Chicago Athletic Association
Dec. 4, 2025 – Jan. 16, 2026
Head to the historic Chicago Athletic Association in the Loop for Happy’s Bar, their annual Christmas pop-up bar. Covered in “décor that will transport you back to grandma’s basement”, Happy’s is taking over the ground floor of the historic hotel for the eighth year. Patrons will be greeted with cozy winter cocktails and bar bites, favorite festive tunes, and lots and lots of glittering lights.
Christmas Club in Country Club
Nov. 14, 2025 – mid-Jan. 2026
Wrigleyville’s original holiday pop-up event, Christmas Club, turns two floors into a full-on holiday playground. Live DJs keep the party going all season long, spinning holiday hits and dance-floor favorites.
With dedicated party rooms and multiple bars, this pop-up is built for big groups, spontaneous nights out, and full-throttle celebration. No cover, no reservations (unless you have a large group or party) — simply walk in and let the holiday mayhem begin.
Winter Wonderland at I|O Godfrey
Nov. 22, 2025 – Jan. 31, 2026
Take your winter festivities to new heights at I|O Godfrey’s rooftop Winter Wonderland — a picture-perfect escape above the city. This open-air space defies the chilly weather with heated, transparent igloos nestled among a forest of glittering lights and luminous decor. Sip holiday cocktails, share bites from the curated menu, and cozy up with friends under a sparkling skyline. With intimate igloos for up to eight and the return of the legendary Big Igloo for 10, it’s a festive retreat like no other. Book your igloo today.
The Christmas Inn at Hubbard Inn
Nov. 13, 2025 – Jan. 2, 2026
The Christmas Inn brings nonstop holiday fun to Hubbard Inn with weekly themed events. Sip festive cocktails during Ho Ho Happy Hour, craft and unwind on Tuesdays, or go dancing on Wednesdays during The Naughty List ladies night. With giveaways, music bingo, and cozy vibes, it’s the ultimate spot to celebrate the season. Come for the cheer, stay for the memories.
More Christmas bars and holiday pop-ups in Chicago
- Frosty’s Christmas Bar (opens Nov. 12, 2025)
- Lakefront Lodge at Harry Caray’s Tavern (opens Nov. 17, 2025)
- Elf’d Up at Stretch Bar & Grill (opens Nov. 8, 2025)
- Reindeer Games at Headquarters Beercade River North (opens Nov. 2025)
- Sugar Plum Parlour at The Albion Manor (Nov. 28, 2025 – Jan. 3, 2026)
- Rudolph’s Bar at Lost Never Found (Nov. 14, 2025 – Jan. 4, 2026)
- Holly Jolly Bar at Puttery (Nov. 13 – Dec. 28, 2025)
- Gwen’s Winter Curl & Chill (Nov. 22, 2025 – March 8, 2026)
- Sleigh Barat Sheraton Grand Chicago Riverwalk (Nov. 21 – Dec. 30, 2025)
