Nine Places to Debauch Yourself with Friends this Season

Nine Places to Debauch Yourself with Friends this Season | Chicago Things To Do | Groupon

Although the holidays are touted as the season of selfless giving, the ready availability of eggnog and mulled wine encourage the indulgence of more earthly pleasures. We found nine Chicago events that embrace the more depraved spirit of the season.

For the Boozehounds

SantaCon at Congress Plaza Hotel

If a run-of-the-mill pub crawl doesn’t put you in a jolly enough spirit, then strap on a red velvet suit for a journey that Kris Kringle wishes he could take each Christmas Eve. From noon onward, hundreds of Santa clones will stumble merrily to six bars—including Bar Below and Celtic Crossing—with photo stops in front of the Art Institute and Millennium Park’s Cloud Gate. (520 S. Michigan Avenue. Saturday, December 7, at noon. Admission: $10 in advance/$15 at door.)

15th Annual Christmas & Winter Beer Tasting at Delilah’s

With probably the largest whiskey selection in Chicago (more than 600 varieties at last count), it’s no wonder people flock to this Lincoln Park punk bar to warm up. Delilah’s holiday party, however, spotlights speciality beer—including winter vintages from Anchor and King & Barnes as well as holiday brews from Three Floyds and Lakefront breweries. (2771 N. Lincoln Avenue. Saturday, December 7, from noon to 5 p.m. Admission: $20 for 20 tasting tickets.)

"Happy Holly-daze: A Drinking Game Performance" at Cornservatory 

Improv theater Corn Productions is known for hosting rowdy late-night BYOB drinking games, so it’s no surprise to see them mixing alcohol, wit, and seasonal debauchery. You bring your poison of choice, and their team of comedy gladiators takes care of the rest. (4210 N. Lincoln Avenue. 8 p.m. Thursday–Saturday from December 12 to December 28. Tickets: $7 on Thursday; $15 on Friday and Saturday.)

For the Theater-goers Who Don’t Blush

"Old Jews Telling Jokes" at Royal George Theatre

It’s not quite a holiday show, but if you’re missing your zaide’s wicked sense of humor this Hanukkah, then this five-actor revue just might fill the void. But be warned: creators Peter Gethers and Daniel Okrent promise to reinvent the classic jokes, so don’t roll your eyes until you hear the punchline. (641 N. Halsted Street. Through February 16; view the full scheduleTickets: starting at $45.)

"A Sack Full of Coal" at Gorilla Tango Theatre

Though this Bucktown theater is mostly known for mixing burlesque with geek-culture satire, A Sack Full of Coal leans more heavily on the satire, mocking the holiday season’s mix of good will and consumerism. The show also shines a spotlight on the often-overlooked Christmas demon Krampus, who is said to punish naughty children by spiriting them away in a burlap sack. (1919 N. Milwaukee Avenue. Every Saturday at 7:30 p.m. through December 14. Tickets: $15.)

For the Audience Members Who’d Rather Participate

Live Band Karaoke at Schubas

Buying multiple craft brews won’t just soften your inhibitions for holiday-themed live band karaoke—it will also keep kids warm this winter. Proceeds from the bar go directly to Coat Angels, a nonprofit that donates warm outerwear to children from low-income homes. (3159 N. Southport Avenue. Wednesday, December 18, at 8 p.m. Admission: free.)

"Christmas Bingo: It's a Ho-Ho-Holy Night" at Royal George Theatre

The "sisters" behind Late Night Catechism put their own spin on the history of Christmas with an interactive lesson. The audience plays along with bingo cards for the chance to win prizes and (hopefully) not be shamed in front of the entire class. (1641 N. Halsted St. Friday and Saturday at 8 p.m. and Sunday at 3 p.m. through January 5. Tickets: $38.95.)

For the Truly Debauched

"A John Waters Christmas" at City Winery

If the holiday season ramps up your desire for debaucherous camp, then you owe it to yourself to see the King of Filth hold court during a smutty, Christmas-themed one-man monologue. With the noble goal of putting “X back into X-mas,” the legendary filmmaker and author tackles subversive topics ranging from perverted gifts to holiday horror stories. (1200 W. Randolph Street. Saturday, December 1, at 8 p.m. Tickets: starting at $65.)

Vaudezilla Craft Fair at Vaudezilla Studio

Burlesque troupe Vaudezilla puts a brassy spin on traditional craft fairs with a showgirl-themed array of vintage and handmade pin-up crafts and clothing. Decadent sweets from Three Moms Bakery will be on display among the assortment of lingerie and bombshell jewelry from glamorous vendors such as Annie’s Red Hots and Acidic Housewife. (3614 W. Belmont Avenue. December 21. Admission: Free.)

Image courtesy of SantaCon