With the first snow of the year under Chicago’s belt and the turkey sandwich leftovers in full swing, it’s officially time to break out the twinkly lights, cut down Christmas trees, and bust out the dreidels. Many of Chicago’s bars are doing the same, as more spots than ever are decking the halls with over-the-top holiday decor, special drinks in Santa mugs, special events and character appearances, and much more. Here are all 22 jolly pop-up Christmas and holiday bars across Chicagoland this holiday season.Read More
22 Decked-Out Holiday and Christmas Pop-Up Bars in Chicago
It’s the most wonderful time of the year at these Chicago bars
1. Sippin’ Santa at Cortland's Garage Arlington Heights
Suburbanites have their own Christmas pop-up bar this year at Cortland’s Garage in Arlington Heights. Sippin’ Santa is an outpost of the New York-based pop-up bar network from tiki legend Jeff “Beachbum” Berry, offering signature cocktails, plenty of decorations, and more through New Year’s Eve. No cover.
2. Yippee Ki-Yay at The Sixth
Some people debate whether the 1988 action classic Die Hard is a Christmas movie, but Bruce Willis fans shouldn’t debate whether they’ll have a good time at Yippee Ki-Yay. Acclaimed Lincoln Square cocktail bar the Sixth is going all out to become the themed pop-up, offering 15 specialty cocktails, an array of movie Easter eggs, and plenty of destination-worthy decor. It’ll be open every day except Mondays through December.
3. Rudolph’s at Casey Morans
This sports bar is one of the latest to join the Christmas pop-up parade in Wrigleyville. Expect character appearances at Casey Moran’s by Rudolph the reindeer and others, plus themed spaces “Grinch’s Piano Bar,” “Frosty’s Rooftop,” “Rudolph’s Lounge,” and multiple bars, along with plenty of holiday decorations and drinks. Food is also available and ticket prices vary.
4. Mistletoe at Hush Money
The cocktail bar above the sophisticated Mordecai joins the Wrigleyville fun with Mistletoe, offering decor and drinks including “Santa’s Munchies” with Blanco Tequila, Becherovka, cinnamon, horchata, snickerdoodle cookie, and CBD Oil. It’ll be open through the new year.
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5. Santa Baby at Deuces and The Diamond Club
One of the largest over-the-top Christmas bars, Santa Baby, is back again this year at Deuces and the Diamond Club in Wrigleyville. The popular pop-up offers multiple themed spaces and bars including a “Gingerbread Village” with spiked hot chocolates, an “Alpine Ski Lodge” with more cocktails, Santa’s workshop, a DJ booth where Santa Claus spins tunes, and even its large outdoor patio is dressed to the nines with Christmas decor. Tickets are available online and at the door; admission is free in November and on weekdays, and the cost is $20 on weekends in December.
6. Santa’s Workshop at Old Crow Smokehouse
This Wrigleyville barbecue restaurant and sports bar is also part of the pop-up craze this holiday season, proclaiming that ownership “spent over $100K on Christmas décor” at Santa’s Workshop. Expect “rows and rows of 10-foot tall trees and tremendously large Santas,” plus two “12-foot high rocking horses,” cabanas and fireplaces on its second-floor rooftop, cocktails, a kids menu, and more. It’ll be open seven days a week from November 29 through December, with no cover charge.
7. Elf’d Up at Stretch Bar & Grill
Fans of the popular Will Ferrell Christmas movie Elf can flock to this pop-up for a second year. Elf’d Up’s decor pays homage to the fictional syrup-eating adult elf with more than 1,000 elves, an upside-down Christmas tree, wall quotes, and condiment carriers on every table with the “four main food groups” — candy, candy canes, candy corn and syrup. “Buddy the Elf” will make appearances every Thursday through Saturday this year, movie trivia happens the three Wednesdays leading up to Christmas, and specialty cocktails include one with Chila ‘Orchata, Fireball, whipped cream, and Cinnamon Toast Crunch. Free admission.
8. The Christmas Club at the Country Club
Another of Wrigleyville’s most popular pop-ups, Christmas Club at Country Club, is back for another year. The two-floor Christmas party includes three bars offering six naughty and nice shots, house eggnog in souvenir mugs, and snacks such as snowballs and a cheesecake sampler served in waffle cones. No cover.
9. 8 Crazy Nights at The Graystone Tavern
Co-owners Kyle Bagley and Sam Stone of Wrigleyville sports bar Graystone Tavern aren’t Jewish, but they will debut Chicago’s first Hanukkah bar pop-up next month that will run through the entire month of December. They’ll offer Eastern European Jewish classics such as matzo ball soup, latkes (fried potato pancakes), and brisket along with “Manischewitz Spritzers” and boozy sufganiyot — deep fried doughnuts with vodka-infused jelly.
10. Christmas with the Griswold’s at Houndstooth Saloon
The 1989 comedy Christmas Vacation gets the pop-up bar treatment at Houndstooth Saloon in Wrigleyville. Santa will be parked out front of Griswold’s in Cousin Eddie’s RV, handing out hot chocolate and cider. Food includes TV dinners, such as a traditional turkey leg and Aunt Bethany’s Jell-O. There’s a $5 cover or toy donation on Thursdays through Sundays after 5 p.m. It’ll be open through the new year.
11. Krampus at DMen Tap
Krampus-themed D&D, a kids’ Krampus day, and a craft fair are just the beginning of DMen Tap’s European anti-Santa Krampus pop-up, back for a second year in Avondale. A special brew from Revolution Brewing made just for the pop-up called “Fist of Krampus” will be available and a Three Floyd’s takeover is in the works. Goat kebabs, telling on friends at the Krampus naughty wall, and more are on offer from December 5 through 23.
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12. The Naughty List: Ludlow Liquors’ Villains of Christmas
Ownership of this acclaimed Avondale cocktail bar has another darker Christmas pop-up, this time with a theme of iconic bad guys of classic Christmas movies. Ludlow Liquors attendees can expect appearances by the Grinch, Wet Bandits, Hans Gruber from Die Hard and others, plus food and cocktail specials based on the films including a cookie plate paired with milk punch. There’s no cover to get into the pop-up, which runs throughout December.
13. Jingle Bell Square at Lost Lake
One of the most-renowned bars in the country goes Christmas at Lost Lake’s second annual Jingle Bell Square. From November 29 until New Year’s Eve, staff fills the tiki destination in Avondale with festive decor, spiced tiki drinks, and over-the-top holiday flair including a 10-foot Christmas tree.
14. Silver and Golden Teardrops
The normally extremely dark basement bar below Lonesome Rose is lighting things up for the holidays, embracing its name and turning into a gold-and-metallic tinseltown. Seasonal winter drinks will speckle the menu from November 29 through New Year’s Eve, and patrons will be able to bust out a favorite holiday tune during karaoke Thursdays from 9 p.m. to 1 a.m.
15. Last Christmas at Woodie's Flat
This three-floor pop-up in Old Town will be open seven days a week through mid-January with tons of decorations, special events, and themed menus at Woodie’s Flat. Tickets aren’t needed but “there may be a cover on weekends or nights in high demand.”
16. Frosty's Christmas Bar
This three-level, four-bar Christmas extravaganza advertises itself as the largest holiday pop-up in Chicago. Frosty’s, back for a third year, is open late everyday until 4 a.m. and offers singing Santa shows every hour, two dance floors, life size toy soldiers, themed cocktails, and plenty over-the-top Christmas decorations, of course. Tickets start at $15 and the pop-up runs through January 5.
17. Miracle at Sable Kitchen & Bar
Miracle, the network of Christmas pop-ups around the country, is back in Chicago for another year at acclaimed River North cocktail bar and restaurant Sable Kitchen & Bar through December 24. Its menu includes 10 Christmas-inspired cocktails such as a snowball old fashioned, three shots, and snacks such as Christmas ham skewers and holiday stuffing fritters. Other attractions include Victorian-clothed Christmas carolers every day.
18. Reindeer’s at The Swill Inn
Chit Chat Lounge, the basement bar of the Swill Inn in River West, will become “Santa’s dive bar of choice” starting November 29. Reindeer’s offers “holiday dive decor,” holiday drinks, frozen egg nog, a candy cane old fashioned, food such as “next day” pub pizza, and cheap beer on Tuesdays through Sundays through the end of the year.
19. Santa’s Bodega at Bodega
The Siena Tavern guys are turning their fast-casual eatery and shop in River North into a holiday pop-up, opening Santa’s Bodega on December 6 and operating it every Friday and Saturday the rest of the month. Expect holiday cocktails, shots, and decor in the small space, which is also available for private parties of up to 25.
20. Mele Kalikimaka at Cerise Rooftop
The Virgin Hotel’s downtown rooftop bar is going Hawaiian holiday throughout December with this “Mele Kalikimaka” pop-up. Expect tropical Christmas decor and drinks, such as a signature $20 cocktail with rum, caramelized pineapple, mandarin tea, and Meyer lemon served in a pineapple. Free tickets are available here. Edit note: the Virgin scrapped its “Cousin Eddie’s” theme this year and switched to this one. A photo of it is not yet available.
21. Happy’s at Chicago Athletic Association
The Chicago Athletic Association hotel operates Happy’s, a top pop-up bar option to escape the cold after a trip to Christkindlmarket or holiday shopping, on the ground floor on Michigan Avenue for the third year in a row. Expect top-notch holiday cocktails, a new food counter option called Hangry’s, and decked-out decor and special events every day except Sunday through December 24.
22. The Reindeer Room at Tack Room
This South Side holiday bar offers live piano music and well-made cocktails in Pilsen. Staff is making over the Tack Room’s cozy space inside Thalia Hall into the Reindeer Room, adding Christmas trees, tinsel, and more decorations. The pop-up is open Thursdays and Fridays through December 28.
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