frosty's chicago holiday pop up
How Santa decks the halls at Frosty's
FROSTY'S / INSTAGRAM
By Claire Young / December 17, 2019 10:58 am

If spending the holiday in a bar conjures sad images of poorly lit rooms with “Blue Christmas crackling” on a fuzzy radio … you’re in the wrong bar. Because if you know where to look, few places are taking holiday spirit more seriously these days than Chicago’s various and sundry seasonal pop-up bars.

For the uninitiated, pop-up refers to a temporary adjustment to an existing offering or retail storefront. Sometimes a business takes over a storefront (as is the case with the Portilo’s experience, now open at Woodfield) and other times, existing businesses reward customers with a fun gimmick. The latter is the case with most of the bars on our list, and, as we reported last summer, the pop-up trend is here to stay

Dozens of bars in the area have gone all-out with holiday decor, which, in concert with strong drinks, is sure to put you in a holly jolly mood. The options vary widely, so we created a handy list (and checked it twice) to help you find the perfect holiday bar for whatever you’re looking for.

For the ‘Gram: Frosty’s A Christmas Bar
809 W Evergreen Ave, Chicago, IL 60622

The folks behind Jack’s Pumpkin Pop-up and Neon Summer bring us their Christmas installment. Life-sized toy soldiers, light coverage that puts Clark Griswold to shame, ribbons, wreaths and candy canes as far as the eye can see adorn the North & Clybourn location. A true pop-up, this winter wonderland took over an empty parking lot to erect a winter wonderland with four bars, three stories and a 4 a.m. last call. Tickets start at $20.

The Christmas Club at … The Country Club

For the Wrigleyville Scene: The Christmas Club
The Country Club | 3460 N Clark St, Chicago, IL 60657

TBOX is over, but the festive bar scene remains. If you want to feel young again, positioning yourself in party central gives plenty of access to the bars in the area, most of which are doing some top notch holiday decorating. The Christmas Club calls itself Wrigleyville’s original Christmas pop-up, and they don’t have a cover, so start your journey there. More Clark Street bars continue below …

For Country Music: Santa’s Workshop 
Old Crow Smokehouse 3506 N Clark St, Chicago, IL, 60657

Mount a 12-foot high rocking horse, hop into Santa’s sleigh (it’s on the roof), then snap a photo with a giant Ralphie in full pink bunny suit. Management is clearly trying to create photo opportunities for patrons, and there’s plenty to look at. Live music on Fridays and Saturdays throughout December.

For Movie Fans (Elf Edition): Elf’d Up
Stretch Bar & Grill | 3485 N Clark Street, Chicago, Illinois 60657

Buddy the Elf cutouts, condiment containers featuring the four elf food groups (candy, candy canes, candy corn and syrup) and a drink list populated with the likes of Mr. Narwhal and Son of a Nutcracker cocktails. If you’ve ever wondered what Buddy’s Breakfast Pasta tastes like, the concoction of spaghetti, maple syrup, chocolate fudge, chocolate syrup, mini marshmallows and strawberry frosted pop tarts can be yours for $9.

Looks like Cousin Eddie made it

For Movie Fans (Christmas Vacation Edition): Griswold’s
Houndstooth Saloon | 3369 N Clark Street, Chicago, IL 60657

The Houndstooth covered their bar in a Griswoldian light grid, then shoved Cousin Eddie’s RV out front, nestled under the L. It’s a sight to behold. Commitment is key, so films nods abound inside, including on the menu, where you’ll find Aunt Bethany’s lime jell-o, fake cat food included. (If you’re in the mood to dress the part, we’ve broken it down for you here.) $5 or a toy donation for Toys for Tots gets you in the door.

Hello, Manischewitz sangria

For Hanukkah: 8 Crazy Nights
Graystone Tavern | 3441 N Sheffield Ave, Chicago, IL 60657

The decor and drinks are a welcome departure from standard holiday fare, but the food is what really sets this stop apart. The menu is stacked with latkes, matzo ball soup, brisket, grilled cheese on challah bread and boozy jelly donuts.

Seasonal cocktails at Last Christmas

For the Wrigleyville Scene Without Going to Wrigleyville: Last Christmas
Woodie’s | 1535 N Wells St, Chicago, IL 60610

If you can bring yourself to step out in Wrigleyville, try the Last Christmas pop-up at Woodie’s in Old Town. Basically the same drill in a different neighborhood. Last Christmas also isn’t beholden to a single Xmas movie, with a menu that features nods to a dozen favorites, including Die Hard and Gremlins. Be advised there may be a cover charge if it’s busy. Nothing says holidays like surge pricing.

For a Good Dive Bar Feel: Reindeers
Chit Chat Lounge | 415 N Milwaukee Ave, Chicago, IL 60654

Located in the basement of River West’s Swill Inn, the Chit Chat speakeasy is transformed into a bar that burnt-out elves would frequent. The folks in charge describe Reindeers as “Santa’s favorite dive” and the menu’s mix of hot, frozen and big-batch cocktails would keep Mr. Kringle occupied. There are also $5 beers and chicken nuggets, if that’s more your speed.

For Beer Fans: Krampus at D-Men Tap
DonerMen Tap | 2849 W Belmont Ave, Chicago IL 60618

The Austrian antonym to St. Nick is the half-goat, half-horror movie villain known as Krampus. If you can get past that (and the associated skull decor), Revolution Brewery created a beer — aptly named Fist of Krampus — specifically for this event. Sip on the custom brew and grab a lamb kebab.

For Cocktail Fans: The Reindeer Room at Tack Room
1227 W 18th St Chicago, IL 60608

Thalia Hall’s Tack Room is a cozy cocktail joint on the historic Pilsen property. Their pop-up, called The Reindeer Room, specializes in brunch and live entertainment, so book a trip when a show is queued up. Options include a “Soul Christmas Jam Session,” stand-up comedy and a holiday drag brunch.

For Suburbanites: Sippin’ Santa at Cortland’s Garage
1 N Vail Ave, Arlington Heights, IL 60005

For anyone that’s ever had Mele Kalikimaka stuck in their head, this sports-joint-turned-tiki-bar will have you feeling warm and cozy in no time. Cortland’s partnership with Sippin’ Santa makes it one of 27 locations across the country serving up Kris Kringle Coladas and Festivus Flip cocktails. The seasonal drinkware alone is worth making the trip to Arlington Heights for the burb’s first Christmas pop-up.

For a non-Pop-Up Christmas Bar: Butch McGuire’s
20 W Division St, Chicago, IL 60610

Before there were pop-ups, there was Butch McGuire’s. The family-owned Gold Coast saloon has been in business since 1961 and earned a reputation for hanging holiday decorations. Every December the in-house team makes and hangs their own decorations, including an operational toy train that loops the bar. It’s not a gimmick and it’s not a pop-up, and Bobby McGuire is even working the door most nights in December. Don’t plan on drink or food specials, just holiday ambience for the sake of coziness and cheer.