From John Belushi and Bill Murray to Stephen Colbert and Tina Fey, the roster of comedians whose careers launched from Chicago’s stages is staggering. In fact, it’s no exaggeration to say that a stint in the city’s become an all-but-mandatory waypoint for wannabe comics en route to stardom. So how did this decidedly non-glitzy Midwestern town come to be the country’s comedy kingmaker?   

empty stage lit in blue, lavender and violet lights awaits an audience in Chicago
Chicago's stages have nurtured some of the world's top comedic talents. Image of the Del Close Theater by iO Theater

Back to the beginning: Chicago comedy's early days

It all started in 1955, when a group of young Hyde Park actors formed the Compass Players, forgoing scripts and applying improvisational exercises learned from one member’s mother, a theater educator, to their cabaret-style revue. And with that, a tradition was born. In 1959, a year after the Players split, three members – Paul Sills, Bernard Sahlins, and Howard Alk – set up shop in Old Town, founding a little troupe you might have heard of: The Second City.  

Since its inception, the Second City’s revues have been sharp and biting commentaries on life, politics and anything else that falls in the crosshairs of their hard-hitting wit. No matter the subject, the delivery vehicle remains the same: improv, often guffaw-inducing and always impressive for its display of mental nimbleness. Cue the formidable procession of comedic geniuses who’ve passed through its vaunted halls, and the raucous crowds that continue to pack the nightly Mainstage revues (and more intimate e.t.c. and Up Comedy Club performances) nearly 60 years on.

person walks in front of Chicago's Second City Improv theater's neoclassical facade
From its home in Chicago's Old Town, improv legend Second City has been cracking up audiences for nearly 60 years. Image by The Second City

Another a charter member of the local scene is the iO Theater, whose founder, Del Close, also served as mentor to many Second City leading lights. Since its creation in 1981, iO’s claim to fame has been its emphasis on long-form improvisation. Worth seeking out is the theater’s resident Improvised Shakespeare Company; players start from a single audience suggestion and go on to weave a hysterical two-act tale inspired by the Bard.

Modern laughs: New comedy venues

Parents who don’t want to slap the earmuffs on their brood every time a scene takes a bawdy turn will appreciate CSz, the long-running theater that’s home to ComedySportz, a family-friendly improv experience. Shows here take on a competitive edge, with two teams striving to out-improv each other through a 90-minute series of games and scenes. On the other end of the politeness spectrum, local mainstay the Annoyance Theatre established its no-holds-barred reputation in the late 80s with the improvisational musical Coed Prison Sluts.

In no small part because of the Second City’s long shadow, a typical evening of humor in Chicago is much more likely to come from improv and sketch comedy than stand-up. But look beyond the city’s signature comedic forms and you’ll find a robust comic-and-a-mike tradition, too. Good for a (frequently raunchy) laugh since it was founded in the back of a diner almost 20 years ago (it’s since moved up in the world, to Lakeview’s Under the Gun Theater) is the Lincoln Lodge, an 80-minute stand-up showcase broken up by live man-on-the-street segments. And each Tuesday, Roscoe Village bar Beat Kitchen hosts Chicago Underground Comedy, featuring local up-and-comers. You never know when you might catch the next big thing.  

group of comics in red hats pour ingredients into a bowl as part of a comedy skit
The not-safe-for-kids Lincoln Lodge is one of Chicago's best stand-up showcases. Image by Sarah Larson / Lincoln Lodge

Some of the city’s best comedy experiences resist easy labels. Experimental theater troupe the Neo-Futurists’ signature piece, The Infinite Wrench, comprises 30 plays that unspool over a mere 60 minutes, to often-absurdist ends. NPR’s Wait Wait Don’t Tell Me enlists a panel of smart-aleck pundits to poke fun at the week’s news; those lucky enough to snag tickets can sit in on a Thursday night taping at the Chase Bank Auditorium. And any given installment of the Paper Machete, a “live magazine” held weekly at historic Uptown jazz venue the Green Mill, might mix stand-up sets and comedic essays with musical performances and dramatic monologues.  

A festival of punchlines

Hardcore chuckleheads will appreciate the diverse assortment of comedy festivals that pop up around the city throughout the year. Lakeview’s Stage 773 alone claims a trio: the flagship Chicago Sketch Comedy Festival, aka Sketchfest; geek culture celebration the Chicago Nerd Comedy Fest; and the female-dominated Chicago Women’s Funny Festival.

fairy lights and banners deck a high ceiling above a crowd of people gathered for Sketchfest
Comedy fans mob Studio 773 each year for Sketchfest, one of three festivals held at the venue. Image by Stage 773

Helped along by the comedy cachet of its sponsor, the Onion, the 26th Annual Comedy Festival draws established comics like Patton Oswalt and Nathan Fielder. But the biggest stage of all is the biennial Chicago Improv Festival, which brings together scores of acts, from fresh-faced college teams to seasoned pros like Rachel Dratch and Scott Adsit for a hilarious weeklong improv jamboree that would do the Compass Players proud.  

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