It’s officially time to break out the twinkly lights, post photos of the CTA’s Holiday Trains, and bust out the ugliest red-and-green sweater around. Many of Chicago’s bars and restaurants are doing the same, as more spots than ever are decking the halls with over-the-top holiday decor, special drinks in souvenir mugs, themed trivia, donation opportunities, and much more. Here are 20 jolly pop-up Christmas and holiday bars across Chicagoland this holiday season.
Read MoreThe Jolliest Holiday and Christmas Pop-Ups Around Chicago
It’s the most wonderful time of the year at these bars and restaurants
Home Alone Christmas at Cortland's Garage Arlington Heights
Suburbanites have their own Christmas pop-up bar at Cortland’s Garage in Arlington Heights: Home Alone Christmas, a tribute to Macaulay Culkin’s 1990 hit holiday comedy that happens to be set outside Chicago. Attendees can expect thematic holiday drinks and a food menu with options like Uncle Frank’s Finger Foods (think cheese curds and Buffalo wings) and Wet Bandits wraps and salads.
Lumberjack Lodge at Smoke Daddy
The Wrigleyville barbecue spot has brought back its cozy lodge pop-up that’s decked out with Christmas trees, skis, logs, and garlands. Attendees are encouraged to don their snuggliest flannels, snap some pictures with a 7-foot-tall bear, and order Campfire Cider (bourbon, cider, allspice), Nutty and Nice (Bailey’s, amaretto, Frangelico, coffee liqueur), or a “shotski” of peanut butter whiskey or bourbon cream. The pop-up runs through Monday, January 8. Make a reservation via Tock.
Mistletoe at Mordecai
For the fifth year, the Wrigleyville bar packs its upstairs space with tinsel, wreaths, ornaments, lights, giant candies, and themed throw pillows. The pop-up has its own menu with a mix of contemporary cocktails like the Gingerbread Milk Punch (brandy, rum, scotch, “all the winter spice”) and drinks that spotlight Mordecai’s collection of rare and vintage spirits, such as a Winter Old Fashioned (Mordecai 3 Barrel Blend, 1960s alpine amaro, 1950s kapirol, maple). The pop-up runs through Saturday, January 6 and reservations are available through Tock.
Santa Baby
One of the largest over-the-top Christmas bars, Santa Baby, is back again in Wrigleyville. The popular pop-up offers multiple themed spaces and an extensive menu of kooky yuletide creations, including group-size drinks like Tropical Sleigh Ride (tequila, pineapple, strawberry, Red Bull Yellow Edition) and Moet Mistletoe (Moet Ice, Duo Limon). There are also tons of hot and boozy options, plus Christmas spins on classic cocktails and booze-free milkshakes smothered in cookies and candy. The pop-up runs through early January, and reservations are available online.
Elf’d Up at Stretch Bar & Grill
Elf’d Up, an annual pop-up themed after Will Ferrell’s absurdist Christmas movie Elf, has returned for its sixth year with floor-to-ceiling decorations including more than 1,000 elves of all shapes and sizes, a 10-foot Christmas tree, and condiment carriers stocked with the “four main food groups” — candy, candy canes, candy corn, and syrup. If that’s not quite enough sugar, patrons can try Buddy’s Breakfast Pasta (spaghetti topped with maple syrup, fudge, and mini marshmallows).
Christmas Club
Another edition of Wrigleyville’s most popular pop-ups, Christmas Club at Country Club, is back for 2023. The two-floor Christmas party includes three bars offering six naughty and nice shots, house eggnog, and snacks such as frosted Christmas sugar cookies served with a glass of milk, and “Baby Cheesus” battered cheese curds. More details are available online.
Let It Snow at Le Sud
This Roscoe Village restaurant’s Let It Snow pop-up is back with its annual family-friendly affair featuring festive food and drink in its main dining room, salon, and enclosed sidewalk cafe, all decorated for the holiday. Grown-up offerings include lamb pappardelle with brown butter sauce (kale, manchego) and an eponymous “Let It Snow” Christmas sangria (wine, ginger beer, brandy, apple cider, brown sugar cinnamon). Kids can expect ever-popular macaroni and cheese alongside hot chocolate and apple cider. Reservations and more details are available online.
Krampus at DMen Tap
A Krampus-themed D&D game, a kids’ Krampus day, and a pop-up market are just the beginning of DMen Tap’s European anti-Santa Krampus pop-up, a particular favorite among those who favor punk rockin’ around the Christmas tree. A special brew from Revolution Brewing made just for the pop-up called “Fist of Krampus” will be available along with gluwein and other themed cocktails. The festivities kick off on Friday, December 1, with a parade through Avondale featuring punk rock marching band Environmental Encroachment.
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Christmas Town at Replay Lincoln Park
The Nightmare Before Christmas is typically associated with Halloween, but in 2023, Jack Skellington is hanging around for the holiday season in Lincoln Park. This arcade and rotating pop-up bar will on Friday, December 1, unveil its Christmas Town pop-up — a “twisted wonderland” where spooky scares meet sugar and spice. There will be tons of themed cocktails, photo-ops, and events like Tim Burton trivia nights. The pop-up runs through Sunday, January 1 and more details are available online.
Tinseltown at The Pink Squirrel
Book one of the Logan Square bar’s two duckpin bowling lanes or just drop in and grab a booth or a seat at the bar and order a festive boozy milkshake. Open for its fourth year, Tinseltown is packed with plenty of its namesake decorations as well as ornaments, reindeer, snowflakes, and presents. Book reservations via Tock.
Jingle Bell Rock at Brando's Lincoln Park
Instead of caroling in the cold, sing some holiday tunes at this Lincoln Park karaoke lounge, which is this year giving a nod to the Plastics’ (of Mean Girls fame) infamous rendition of the Christmas standard “Jingle Bell Rock.” A menu of “winter warmers” includes the Santa’s in Mexico (reposado, white cranberry juice, coconut) and spiked hot apple cider. The pop-up runs through Sunday, January 7.
Frosty's A Christmas Bar
Holiday music plays nonstop from 7 p.m. to 4 a.m. daily through Sunday, December 31 at this staple Christmas pop-up in Lincoln Park. Party people can expect four bars and two dance floors spread across two levels packed with decorations including giant toy soldiers, ornament-shaped chairs, and shining trees. Visit with Santa and sip some themed cocktails or splurge on bottle service. Tickets are available online.
Reindeer Games at Headquarters Beercade
The Nashville pop-up returns to Chicago this year, packing the River North bar with photo opportunities like naughty-and-nice thrones and a full-sized sleigh. Festive drinks include Partridge in a Pear Tree (Bombay Bramble, spiced pear liqueur, ginger ale) and Santa Snack (blanco tequila, apple pie liqueur, hard cider). Reservations are available via OpenTable.
A Very Dandy Holiday Pop-Up at The Dandy Crown
Beverage director Sarah Syman provides a very spirited holiday with cocktails emphasizing nostalgia and winter flavors. Warm up with hot crockpot cocktails or indulge in seasonal drinks like Ghost of Christmas Past (reposado, bianco, genepy, chocolate, lemon) and All the Jingle Ladies (citrus vodka, ginger shochu, sparkling cranberry bubbles). The pop-up runs from Friday, December 1 through Sunday, December 31, and offers plenty of free gatherings including trivia, a holiday comedy show, and an ugly sweater event that doubles as the bar’s fourth birthday party. Make a reservation on Tock.
Chef Art Smith’s Reunion
Chef Art Smith’s Reunion, a rare restaurant heavyweight at tourist-laden Navy Pier, is getting punny with the North Pole with its Santa’s Southern Workshop pop-up every weekend through Saturday, December 23. Smith and his team are offering a three-course prix fixe menu for adults (there’s a shorter selection for kids) with regional favorites like fried green tomatoes and shrimp and grits, as well as visits with Mr. Claus. Reservations and additional details are available online.
The Christmas Inn: Holidays on Hubbard Street
River North nightclub Hubbard Inn aims to delight celebrants with three floors of Christmas cheer, as well as a wide range of activities like an ugly sweater party, mixology classes, and a weekly holiday trivia night with prizes. Patrons can explore the holiday madness while sipping hot and cold drinks. The pop-up runs through Sunday, December 31. Reservations and more details are available online.
Christmas Town Holiday Lounge at Recess
Several Chicago bars this year are embracing the Christmas side of The Nightmare Before Christmas, including Recess in West Loop. The team has kicked off a Christmas Town Holiday Lounge pop-up, offering Chicagoans an opportunity to venture through a Christmas village inspired by the 1993 animated musical, as well as scenes from the film such as a kidnapped Sandy Claws on a saw wheel and a 13-foot sculpture of the Pumpkin King himself. The sprawling patio spot is prepped for the season with fire pits and outdoor heaters, as well as toasty cocktails and group-size drinks. The pop-up is slated to run through Saturday, December 23 and reservations are available via OpenTable.
Happy’s at Chicago Athletic Association
The Chicago Athletic Association hotel has brought back Happy’s, its popular pop-up bar on the ground floor on Michigan Avenue. Expect decked-out decor with plenty of lights, trees, Santas, stockings, and festive music. Happy’s is open through Friday, December 22.
Holly Jolly Holiday Bar at Electric Garden
Trimmed like a tree from top to bottom, Electric Garden’s Holly Jolly Holiday Bar has gone all-out with tinsel, ornaments, and lights galore. There are also, of course, Christmas-themed cocktails, with some served in mugs shaped like Santa’s boot.
Reindeer Room at Tack Room
The Thalia Hall piano bar is decked out with lights, tinsel, and ornaments through New Year’s. Performances include a Yuletide cabaret on December 15 and a Christmas Eve sing-along. Get some liquid courage before joining in by ordering a seasonal cocktail like spiked hot chocolate, a gin & tonic blended with house made cranberry syrup, or the Jingle Bird Julep (gin, pineapple, cinnamon, lime, sherry). There’s never a cover.