Chicago has many monikers and "home of improv" fits this city like a glove—a really funny glove. Many famous actors trained and performed here: Joan Rivers, Alan Alda, John Candy, Steve Carrell, Bill Murray, Gilda Radner, Chris Farley, Tina Fey, Amy Poehler, and Stephen Colbert—to name a few. This comedy town is a deep well for talent, one that seems to replenish Saturday Night Live with new cast members on a regular basis.
Annoyance Theatre & Bar
If you've been wanting to see one of the longest-running musicals in Chicago's Boys Town, pop over to the Annoyance Theatre & Bar. Warning: the musical is called Co-Ed Prison Sluts. For over 30 years, uncensored acts have been performed on the main stage, entertaining visitors from near and far with sketch comedy, improv, full-length plays, cabaret, and big ole musicals.
The ComedySportz Theatre
Finally, a comedy show that is appropriate for families..well, except for the late-night shows, which can be a bit raunchy. If you like a little healthy competition, and who doesn't, The ComedySportz Theatre is for you. Dueling improv troupes go back and forth, while a ref keeps score, for this interactive show that is centered around crowd participation.
Hyde Park on Chicago's south side is home to one of the best improvisational comedy clubs in the city: The Revival. Laugh from your seat at one of the weekend shows or consider performing yourself. The Revival offers classes, workshops and camps for prospective comedians—go see what you're made of at an open mic.
Laugh Out Loud Theater
Laugh Out Loud Theater has several show choices, with varying times, to choose from: Same Time Next Door, Comedy Court, Jane Bond, She-Zam, and Booze Your Own Adventure are among the best. Monday Fun Day happens on, you know, Mondays. Definitely grab a drink before or after the show at the vintage bar, which was refurbished to its 1930's glory.
Sundays are reserved for open-mic comedy at Gallery Cabaret, which means guests never know what they'll get. Sets get raunchy, slapstick, personal or whatever else the comics feel like doing. But it's bound to be entertaining at this Bucktown mainstay that includes a complimentary buffet, beginning at 8 p.m. There's also comedy every Thursday, and all shows are free.
The Comedy Bar
Completely under the radar in the nightlife-focused River North neighborhood, The Comedy Bar is on the third level of Gino's East--the legendary Chicago-style pizza parlor. This is especially great for hungry patrons who can order a deep-dish pie or two to chow down as they watch performances. Local acts are featured with a mostly Chicagoan crowd, but the laughs are universal. Additional comedy sets, plus live music, occur on the first floor of the venue at 9 p.m. Thursday through Saturday.
Improv vet Charna Halpern opened the sprawling iO Theater in 2015 in Lincoln Park, and it boasts four theaters, two bars and an expanded training center for those looking to get into the business. No visit to iO is complete until guests check out the Monday night "The Armando Diaz Experience." That just happens to be Chicago's longest-running improvised comedy show, and its full name is "The Armando Diaz Theatrical Experience Movement & Hootenanny." It was founded by Adam McKay (SNL, Anchorman, Talladega Nights), Dave Koechner (Anchorman, Thank You For Smoking, SNL) and iO Armando Diaz. The two-act, "long-form" improvised show consists of a monologist telling personal stories that inspire scenes by that show's cast.
Do you love watching celebrity roasts on Comedy Network? You're certain to get wicked pleasure from the weekly takedowns at the Laugh Factory outpost in Lakeview. It's called "Afterthoughts: A Comedy Roast Show," and it's a chance for comedians' friends to strike back. While they're performing, their friends write mean jokes about them, which are then read aloud to the audience. It happens at 8 p.m. every first and last Monday of the month. Also, late-night owls should head here on Fridays for the "Midnight Madness" performance, which kicks off at 11:59 p.m.
Where To Dine Nearby: Check out DryHop Brewers, which is a few doors down.
Fridays at Lincoln Lodge are reserved for stand-up comedy, and it's a favorite pastime in Bucktown. Shows start at 8 p.m., and the 80-minute show is a hoot, concentrating on a variety act, "Man on the Street" segment and more. This event has been going on for almost 20 years at this location.
Where To Dine Nearby: Across the street is The Robey hotel, so a trip to Cabana Club, Robey Cafe or Up & Up rooftop lounge is a great idea. Also in the area are Big Star, Pork & Mindy's and Publican Anker.
The Second City
The legendary sketch comedy venue that launched the careers of Alan Alda, Jim Belushi, Dan Akroyd, Bill Murray and others just keeps cranking out the talent. There are four venues in one at The Second City — Mainstage Theater, E.T.C. Theater, Up Comedy Club and the Training Center — and each boasts a distinct style. One of the highlights at Up Comedy Club is "Fast, Loud & Funny," which takes on pop culture, Millenials and more in raw fashion. It happens at 8 p.m. Tuesday and Wednesday and 4 p.m. Saturday.
Also in Old Town, Zanies is a top attraction because many of its headliners are major stars. Past performers have included the likes of Jerry Seinfeld, Jay Leno, Tim Allen, Craig Ferguson and Chelsea Handler. It is the third longest continually operating comedy club in the country. There are additional locations in Rosemont and St. Charles.