Fiercely loyal sports fans, deep dish pizza, windy weather, and the glistening Lake Michigan in the summer are all to be expected if you’re looking to move to Chicago and into one of the properties offered by Chicago real estate brokerage firm Related Realty. What you might not know about your future hometown is that Chicago is also the funniest city in America. The city has edged out New York and Los Angeles, with nothing short of a renaissance in comedy culture that encompasses a crop of new venues, rising talents performing every night of the week, and new hometown heroes such as breakout television star Hannibal Buress.
Chicago is a city with a rich history of comedy stretching back to the vaudeville era of the late 19th century, when massive theaters like the Folly, the Palace, the Haymarket, and the Majestic opened, and Chicagoans got their laughs from traveling revues and local funnymen. It wasn’t until the mid-20th century that Chicago cemented its place in the American comedy canon as the birthplace and hub of modern improvisational comedy and the training ground for countless 20th-century comics like Joan Rivers, John Candy, Dan Aykroyd, Chris Farley, Amy Poehler, and Amy Sedaris.
Today it’s not hard to find intimate local venues throughout the city to catch up-and-coming talent and established heavyweights. Here’s a guide for navigating some of the city’s funniest spots:
Zanies | 1548 North Wells Street For nearly 40 years, Zanies has been a mainstay on the Chicago comedy circuit, nurturing the careers of such comedy superstars as Roseanne Barr, Jay Leno, and Jerry Seinfeld. This stand-up showcase features weekly shows from local and national acts and also offers classes providing basic instruction on stand-up comedy, including the history of the medium, how jokes work, and how to create an act that stands out from the rest.
Second City | 1616 North Wells Street This legendary Chicago venue and school single-handedly birthed the genre of improvisational comedy in the US, and since its founding in the late 1950s, has groomed scores of successful entertainers, writers, and directors in its home city, including the lion’s share of Saturday Night Live cast members—Julia Louis-Dreyfus, Bill Murray, Tina Fey, to name just a few—Steve Carell, Stephen Colbert, and most of the cast of 30 Rock. You can catch the next in line of America’s comedy legends any night of the week on Second City’s revered Mainstage Theater, as well as performances in the venue’s smaller theaters—UP, Donny’s Skybox, or the de Maat Studio—to see stand-up, student work, or experimental sketch comedy.
Jokes and Notes | 4641 South King Drive Chicago’s black comics put this woman-owned South Side venue on the map after it opened in the early 2000s, and local talent continues to set the stage ablaze during open mics on Wylin’ Out Wednesdays and monthly Thursday showcases hosted by a rotating cast of hilarious hosts. Each weekend, national acts (past guests include Mo’nique and Bill Bellamy) bring high-caliber comedy to the 150-seat club and swank lounge area.
Laugh Factory | 3175 North Broadway Street The Chicago outpost of this Los Angeles comedy institution opened its 400-seat theater in 2012, bringing an additional permanent venue for stand-up comedy to this improv-obsessed town. With a calendar packed with nightly stand-up showcases, open mics, themed festivals, and midnight programs, the Laugh Factory has proved itself an indispensable destination for stand-up lovers.
iO Theater | 1501 North Kingsbury Street
Another mecca for improv comedy is the iO Theater (its initials originally stood for ImprovOlympic Theater). Founded by Charna Halpern and Del Close, two heavyweights in Chicago’s 1980s improv scene, iO bills itself as the premiere place to see long-form improvisational comedy in the city. The Wrigleyville venue offers four theaters, a bar, a training facility for classes, and an events space. Veteran improv ensembles and student teams perform nightly in a range of approaches to the popular comedy form.
