It can be overwhelming trying to decide where to see comedy in Chicago. Once you start looking, there’s a seemingly endless list of showcases every week, and, thanks to an embarrassment of riches when it comes to talented comics in Chicago, most of them are a guaranteed good time. Still, there are standouts. This list features the results of a quick informal poll of some local comics—the people who arguably see more comedy than anyone—combined with some of my personal favorites, shows that have inclusive lineups, creative concepts, or were simply just a blast to attend in 2019. Lucky for you, they’ll still be going strong in 2020.
Every Thursday at rotating venues, Arts & Culture Club gives performers the chance to nerd out about that week’s topic, whether it’s as broad as “online” or as specific as “Drake.” Expect a night of comedy, PowerPoint presentations, music, costumes, storytelling, and, in one instance, a pair of anonymous masked dancers whose identity is still unknown, one of the greatest sagas to follow on Instagram this year.
Cupcake Comedy Cabaret, every Thursday at Gallery Cabaret, lives up to its name. The weekly showcase features comedians, cabaret performers like burlesque dancers or magicians, and freshly baked cupcakes. There’s an open mike beforehand for anyone feeling inspired to try out some jokes of their own.
Sleeping Village is slowly becoming one of my favorite “not a comedy venue” venues, and that’s in part because of the monthly showcase Just Us Gals. The lineup consistently features some of the most hilariously bizarre comics in the biz, with a focus on women, nonbinary folks, and queer performers.
A recent report from the Comedy Club Database (another great innovation for comedy in 2019) showed that less than 1 percent of comics booked at 55 different clubs across the country were Latina. Las Locas Comedy is working to change that. Every month at Dstrkt Bar and Grill the show features a lineup of primarily Latinx stand-ups—and a few lovingly called “honorary locas.”
If you’ve ever wondered whether your favorite stand-ups can also sing, then Low Key Karaoke is for you. Every Tuesday at Northside Bar & Grill comedians perform jokes and then sing a karaoke song. An open mike follows, and anyone who sings can add another minute into their set—the person with the best set of the night wins a $25 gift certificate to the bar.
The Missy is named as such because each month at the Boxcar two comedians need to put their thing down, flip it, and reverse it. Translation: each of the performers do a ten-minute set while the other is not in the room. The hosts of the show write down keywords as a setlist and then the comedians improvise a brand new ten minutes based on the other person’s set.
Full disclosure: I performed at the Paper Machete this year. But even if I hadn’t, this weekly live magazine at the Green Mill would still top my list as one of the most cathartic comedy experiences in the city. Comedians, musicians, journalists, and one beloved puppet break down the week’s current events, and it feels so much better to laugh until you cry instead of just crying.
Celebrating the body types and expressions of performers on stage makes laughing along to their jokes all the more euphoric. The monthly body-positive stand-up show Strip Joker at Mary’s Attic encourages performers to wear as little or as much as they please, often resulting in an item of clothing being tossed with every punch line.
Everyone loves a good roast. At Toasted, every Saturday at Comedy Clubhouse, stand-ups perform and turn the spotlight on willing audience members with the delicate and time-honored art of the roast. To take the sting out of it, every show ends with a toast celebrating the roasted. v