With the first snowfall having already blanketed Chicago, it’s beginning to look a lot like holiday bar season is upon us.
At some point in Chicago, the holiday pop-up bar became a seasonal signature, along with ice rinks, Christmas Carols and teas. This year brings the standards — with lights and Santa and North Pole ephemera — as well as plenty of twists on the classic, including a Will Ferrell-style, Elf-themed pop-up in Wrigleyville.
While there’s generally no price for entry, most of the spots on the list below encourage reservations. Some are adult-only options, which we’ve noted, but check before you go if you’re taking the family. And a word of advice: Expect that North Pole-themed tiki cocktail to cost a few more dollars than a standard mixed drink in a Downtown bar.
Here are 12 to try.
Wrigleyville, Lincoln Park
Themed bars with Instagrammable photo ops? Wrigleyville naturally booms with options. Santa Baby offers a photo backdrop around every corner and multiple bars for sipping “Jingle Juice” (available in small, medium or mega.) Menu offerings include Christmas nachos made with green and red chips ($23), a Grinch milkshake ($16) that can be spiked for $5, Santa’s smash burger ($21) and an assortment of pizzas ($32-$36). It’s good for groups, especially if you’re still looking for a holiday office party destination. 3505 N. Clark St.
Across the street, Big Star’s Holiday Honky Tonk invites guests to sing, sip, and two-step their way through the festive season. The bar at this popular Tex-Mex destination serves up a spirited lineup of seasonal cocktails. Try the Rhinestone Rita ($15), Big Star’s signature margarita with a glittery prickly pear twist, or cozy up with the Winter Old Fashioned ($13) featuring bourbon and apple cider syrup. For something more festive, order the Mint Espresso Martini ($13), with a candy cane rim. Savor each sip with a soundtrack blending holiday classics and modern country favorites. Seasonal bites include a smokey brisket nacho ($18), brisket tacos ($5), and a cowpoke chili walking taco ($5). Walk-ins welcome. 3640 N. Clark St.
A few blocks down in Wrigleyville, Elf’d Up pays homage to the 2003 movie Elf by featuring 1,000 elf figurines. There’s an upside-down tree, too, and a menu that includes Buddy’s infamous breakfast pasta — spaghetti topped with maple syrup, chocolate fudge, and mini marshmallows ($14). Cocktails, such as the gin-forward Mr. Narwhal, ($17) draw inspiration from the film’s characters and themes. 3485 N. Clark St.
The holiday theme isn’t just for those who celebrate Christmas. “8 Crazy Nights,” Chicago’s first and only Hanukkah-themed pop-up bar, returns this year to the Graystone Tavern in Wrigleyville. The blue-and-white wonderland of more than 30,000 lights opens Friday, Nov. 21 and runs through Jan. 4. Every inch of the bar and its weather-proofed beer garden will be decked out, creating a Hanukkah-haven made of shimmering Hanukkah ball lanterns; Star of David and dreidel ornaments; glowing menorah décor, and an 8-foot inflatable dreidel. The food menu includes a Challah grilled cheese with tomato soup ($12); latkes (starting at $8), a boozy jelly donut ($6); and a brisket sandwich ($16). Specialty cocktails like the “Mega Mensch” ($14), made with vodka, strawberry, ginger beer and lime juice, fancy up the bar’s regular options. If you like board games, this is the destination for you with Connect 4 with Hanukkah gelt, Mitzvah Match, Jewish Guess Who, Dreidel and the Apples to Apples Jewish edition. 3441 N. Sheffield Ave.
As for where the holiday pop-up trend began, owners of Frosty’s claim it’s there in Lincoln Park. Expect, naturally, an over-the-top Christmas explosion party vibe for the next six weeks inside this three-level, four-bar high-energy pop-up. You’ll find the wall-to-wall holiday decor of life-size Nutcrackers, twinkling lights and plenty of garlands fills the adults-only space. Tickets are required and include a timed entry ($18.67). For an additional fee, specialty cocktails (up to three) can be purchased in advance ($31.13-$48.77). The menu includes “The Grinch,” a vodka, green apple, lemon-lime fizz ; “Christmas Cookie,” a vanilla-butterscotch-Irish-cream blend; and holiday shots. Roaming Santas, Grinches and carolers will be guests on rotation when the pop-up opens Friday, Nov. 21. Adults only. 809 W. Evergreen Ave.
Downtown
Frosty’s loves company with two sibling bars. The Nutcracker in River North provides a similar adults-only nightlife experience, with visits from Santa for photo-ops and even a New Year’s Eve party on the books. 15 W. Illinois St. Jack Frost in Fulton Market is more family-friendly and welcomes guests of all ages to participate in outdoor activities such as ice skating, axe throwing and bumper cars. 170 N. Green St.
The tropical setting of Three Dots and a Dash, a haven for people who love cocktails, gets a winter wonderland makeover for the holidays with its River North Pole Pop-Up. Tiki classics such as the Mai Tai have stayed on the menu, but they’re served alongside a piping hot buttered rum cocktail ($15), an eggnog grasshopper ($17) and a whiskey drink made with clarified milk and served alongside chocolate chip cookies ($19). Drinks are offered as singles or big enough for groups of six. Each cocktail lands at the table in eye-popping Christmas glassware (think the bottom half of an elf, a snowman, or even Santa’s head), practically begging to be posted to Instagram. For hungry visitors, the Thai curry crab rangoon dip ($22), firecracker popcorn chicken ($16) and sweet potato fries ($13) are standouts. 435 N. Clark St.
In the heart of the Loop, Happy’s at the Chicago Athletic Association leans hard into Midwestern nostalgia. The space is designed to take you back to grandma’s basement so skip it if you’re not a fan of old-school decor or frightened by the prospect of a lifesize-ish animatronic Santa. On the menu is a double smashburger ($28), mozzarella cheese bites ($12), Nashville hot cauliflower sliders ($16) and apple cinnamon hand pie ($10). Seasonal drinks like “Gin-gle Bells,” a gin, lemon and cranberry cranberry ($16) are available during the pop-up’s run. But if you’re a gambler and more likely to be on the naughty list, order “Santa’s Choice,” a rotating mystery shot done “Santa’s way.” The order includes a souvenir shot glass. 12 S. Michigan Ave.
Not to be outdone, Navy Pier offers a holiday themed pop-up of its own, with a Lakefront Lodge Pop-Up at Harry Caray’s Tavern. Running from November through February, the decor nods to alpine charm — think looking past the tourists and seeing instead a cozy, ski-inspired retreat with sweeping views of downtown Chicago and the icy shimmer of Lake Michigan. Expect a glowing fireplace, rustic holiday décor, DIY s’mores kits, a hot chocolate bar (available as both classic, spiked and super-sized for groups of 6-8, $5, $15 or$98) and private whiskey tastings. The pop-up also offers this year private outdoor curling rinks and heated igloos for rent. 700 E. Grand Ave.
A slight variation on the theme is Chateau Carbide’s Winter Garden, which brings rooftop chalets atop the Pendry beginning Thursday, Nov. 20. Through February 2026, guests can reserve one of the cozy lounges, adorned with tableside fireplaces and fake furs; a menu that includes lobster rolls ($36), baked brie ($20) and braised short rib sliders ($21) alongside chilly season-themed drinks like the Spiced Solstice Margarita ($21). Adults only. 230 N. Michigan Ave.
And JoJo’s Shake Bar makes sure children of all ages get in on the fun with its Winter Wonderland in River North. The bar transforms its outdoor space into an enclosed, heated Santa’s workshop with eight-foot Nutcrackers, a 25-foot Christmas tree and giant ornaments. JoJo’s is known for its outrageous milkshakes, which arrive overloaded with whipped cream, candy and cookies.Take, for example, the Winter Wonderland Biggie Shake ($15): It’s a peppermint shake served with a Christmas tree cookie, marshmallow present, mini candy cane and a snowman made out of a donut hole. Lest you think it’s just for children, adults can spike their beverages with Fernet Branca for $6, or order Santa’s Sangria ($18) and Eggnog shots ($10). Throughout its seasonal run, JoJo’s will host a series of holiday-themed events such as ornament painting, gingerbread decorating and photos with Santa ($30-$48 per person, which includes a food entree, non-alcoholic beverage and activity). 23 W. Hubbard St.