Where You Can Find Must-See Chicago Comedy in 2020
Chicago has been proving grounds for the rising stars of comedy since the birth of improv (which also happened in the Windy City). Here’s where to find them in the year ahead.
In the back of a rundown pancake house on the north side of Chicago in 2009, I watched a comic—one in a lineup of hysterical acts—crack wise to an audience of a few dozen people about riding the El. The event was the Chicago comedy showcase at The Lincoln Lodge, which recently shed its back-of-house status and moved into its own shiny digs on Milwaukee Avenue. And the comic? Kumail Nanjiani, whom you may now know for The Big Sick, a film that earned Nanjiani a Best Original Screenplay Oscar nomination in 2018. (He also starred in it.)
After working more than a decade as a Chicago comedy critic, I’ve stumbled into more than a few of these moments. But you can collect your own stories in one weekend. Past cast lists for The Second City’s sketch and improv shows read like a who’s who of Saturday Night Live stars: Bill Murray. Chris Farley. Tina Fey. Plus rising talent and established names pop up often in small clubs for surprise sets.
The Windy City is both a historical proving ground and a magnet for fresh, inventive comedians in all types of comedy, be it stand-up, improv, sketch or even satirical writing. (True story: The Onion is headquartered here.) Chicago native comedian and producer Dave Helem compares the hardworking comedy scene to a gym. “You get strong here,” he says.
Lucky for you, a comedian can’t build muscle in an empty room. Across the city, you can see amazing comedy in any genre, any night of the week—and often relatively cheaply. Our insider tips for where to watch (and where to eat and stay near the scene) could put you in a room with someone your friends will rave about in five years. And you’ll say, “Yeah, I saw him at a bar in Chicago back in 2020.”
Improv + Sketch
The Compass Players invented improv on the South Side in the ’50s, then moved north to start The Second City. Sixty years later, The Revival launched near the University of Chicago to bring improv back to its roots. The theater also stages sketch revues and stand-up showcases as one of the best places to catch comedy south of the Loop.
The Second City
The Second City comedy empire is one of the major pipelines to Saturday Night Live and now has training programs and theaters in Toronto and Los Angeles. The Chicago flagship hosts multiple shows nightly. The Mainstage is always a winner, but try the e.t.c. Theater for a looser, quirkier and more affordable show.
The io Theater
Also a feeder for Saturday Night Live, iO’s storied training ground, co-founded by Del Close and Charna Halpern, combines multiple theaters, two bars and a kitchen. The city’s best improv goes down here, seven nights a week. Find your favorite performers talking comedy in the bar after the show.
The improvised and scripted shows here are often more subversive, darker and weirder than anywhere else in town. After more than three decades, The Annoyance is still on the cutting edge, so be prepared to laugh and maybe squirm a bit in your seat. The venue serves up bar food and drinks, just a short walk from the CTA’s Belmont stop.
This legendary spot opened in 1978 and is now the fourth-longest-running comedy club in the country. (A second location in Rosemont is near O’Hare airport.) It hosts touring comics and locals nightly. If you’ve heard of a comedian, they’ve been here. Look for a signed headshot on the wall.
Laugh Factory Chicago
Local stand-up comedians take this stage every night. Look for stacked lineups with Chicago headliners, up-and-comers, and current and future stars on a regular basis. The Laugh Factory opened the spacious location in 2015, after a $5 million remodel of an old theater.
Drinking + Dining
The Second City opened this popular upscale bar-restaurant in 2016. Named for the year the company originally opened, it’s the perfect spot to grab a drink and relive the laughs of a Second City show.
Old Town Ale House
For years, the self-described Premier Dive Bar in the World has been a hangout for Second City performers to come in and unwind after a show. Many of them have portraits painted on the wall. A photo of actor Michael Shannon sitting at the bar, watching The Shape of Water win Best Picture at the Academy Awards, went viral in 2018. Enter with open eyes: Bruce Elliott’s provocative political paintings on the walls have made waves nationally.
“Jimmy’s” Woodlawn Tap
A few doors down from The Revival, this casual Hyde Park stalwart has more than just beer on tap. It’s down the street from the Compass Bar site (now a firehouse), where the Compass Players first performed.
Every Wednesday night, this low-key watering hole hosts the most renowned stand-up open mic in the city. Founded by Cameron Esposito in 2009, the weekly five-hour marathon of free comedy is still going strong a decade later, supported by dynamite hosts Alex Kumin and Carly Kane. You can expect cheap drinks and visits from the tamale man. Shows often feature surprise drop-ins from big names like Esposito, T.J. Miller and Hannibal Buress.
While tourists have snapped pics inside Billy Goat Tavern for decades (famous for its “Cheezborgers” on SNL), members of Chicago’s comedy community are more likely to be spotted downing “Slingers” at this 24-7 icon in Lakeview. The Chicago mainstay reopened in 2018 to much fanfare after burning to the ground in 2016.
Three Chicago comedians to keep an eye on in 2020.
Catch this quintessential Chicago storytelling comic in her hometown, when she’s not touring the country with Mo’Nique.
This Southsider headlines around town, including at Zanies, when he’s not touring with comedy superstar Sebastian Maniscalco—who executive produced McGann’s first special (in Chicago) last September.
A straight-talker with a roguish smile and a killer attitude, the Chicago headliner is known for dropping hilariously candid truths in her sets.
10 More Famous Comedians Who Came Up in Chicago
- Stephen Colbert
- Joan Rivers
- Steve Carell
- Bernie Mac
- Amy Poehler
- Dan Aykroyd
- Keegan-Michael Key
- John Belushi
- Gilda Radner
- John Candy