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Date(s)	Supertitle	Title	Subtitle	Venue
Sun, Jun 22 - Sun, Aug 31		$5 Power Hour	These brand-new teams will deliver a guaranteed night filled with notes of laughter, creaky bentwood chairs, and a hint of flannel shirts in this historic incubator for comedy's rising stars.	Dayton Cabaret	buy now »
Fri, Jul 25 - Sat, Jul 26	iO Fest 2025	2 Square	In 2 Square, John Lutz and Peter Grosz take a single suggestion then spin that into a 45 minute longform show featuring the kaleidoscope of scenes, absurdist transitional elements and callbacks.	The iO Theater	buy now »
Fri, Jul 25 - Sat, Jul 26	iO Fest 2025	3Peat	3Peat is a critically acclaimed group of improv/sketch/standup artists who met while performing and teaching at iO and Second City in Chicago. They have gone on to work on a number of different projects like The Blackening, South Side and more.	Fremont Theater	buy now »
Fri, Jun 20 - Fri, Jun 27	The iO Sketch Ensemble presents	Any Time But Now	An all new sketch show every Friday in June.	iO Theater	buy now »
Mon, Jun 23 - Mon, Jul 28	iO Theater Presents	The Armando Diaz Experience	Chicago's Longest Running Improv Comedy Show! Each week, actors will improvise a two act show based on the stories and monologues of a special guest host. This show was invented at iO in 1995 and has been running ever since.	Fremont Theater	buy now »
Wed, Jul 2 - Wed, Oct 1	iO Theater presents	Audrey & a Friend	A monthly sketch show with a rotating cast of performers and one constant, omniscient presence - Audrey Schiffhauer.	iO Theater	buy now »
Thu, Jul 24	iO Fest 2025	BATSU!	Four comedy warriors face off in challenges to avoid painful, humiliating, and ridiculous punishments! The bravest audience members may also volunteer (upon signing a waiver) to participate in some of the challenges to win honor or suffer pu	The iO Theater	buy now »
Thu, Jun 19 - Thu, Jul 31	iO Theater presents	Beverly: A Bevy Show	Join the movement with Beverly as we bring exciting, energetic, and exhilarating improv directly to YOU!	iO Theater	buy now »
Sat, Jul 5 - Sat, Dec 6	iO Theater presents	Binge the Fringe	An Improvised Feast of Festival Flavor	The iO Theater	buy now »
Mon, Jun 23 - Mon, Aug 25	iO Theater presents	Blast!	A rotating cast of improv veterans.	The iO Theater	buy now »
Thu, Jun 26 - Thu, Sep 11	iO Theater presents	Blueprint	Each week, a different cast member designs a bold new format and their fellow performers will learn about at the same time as the crowd. Expect the unexpected as we build something completely original, live, right before your eyes.	Weed Cabaret	buy now »
Fri, Jun 20 - Sat, Sep 27	Malarkey Comedy presents	ComedySportz	The Ultimate Comedy Competition	Kingsbury Theater at iO	buy now »
Wed, Jun 18 - Wed, Jun 25	iO Theater presents	Courtney vs. Cancer	When 26-year-old Courtney is diagnosed with a virtually terminal disease, her world is turned upside down. As she learns to navigate the world of cancer, she challenges the conventional perspective of what a cancer patient’s journey can be, what resi	iO Theater	buy now »
Sat, Jun 21 - Sun, Jul 13	iO Theater presents	Cowboy Joe	A cowboy lost in time, a pathetic 10 year old boy, and a showdown where the heart takes aim - Cowboy Joe brings the Wild West to 2025!	Weed Cabaret	buy now »
Sat, Jun 21 - Sat, Jun 28	iO Theater Presents	The Creamboy Show	Creamy Improv. A Hilarious night. No Lactaid needed.	Dayton Cabaret	buy now »
Sun, Jun 22 - Sun, Aug 31	The iO Theater presents:	Deep Schwa	Chicago's longest-running Harold team returns to iO to bring their unique blend of chaos and creativity to iO's signature form The Harold melding games, songs, and scenes for singular, edge-of-your-seat improv comedy.	The iO Theater	buy now »
Fri, Jun 20 - Fri, Sep 26	iO Theater Presents	Devil's Daughter	Devil’s Daughter features a cast of comedians who have performed together around the country for 8+ years.This award-winning team has their own unique spin on a classic improv form that features an artistic style and a dastardly sense of humor.	Weed Cabaret	buy now »
Thu, Jun 19 - Thu, Jul 10	iO Theater Presents	Duluth: An Improvised Midwest Murder	Each week, Duluth will take you into the (completely improvised) world of true crime in the Midwest: criminals, cops, and the everyday idiots who get caught in-between. Prepare yourself for a world of mayhem, murder, and Minnesota accents.	Dayton Cabaret	buy now »
Fri, Jun 20 - Fri, Sep 26	iO Theater Presents	Escándalo	A Latine variety show PA LA CULTURA!	iO Theater	buy now »
Sun, Jun 22 - Sun, Dec 14	Malarkey Comedy presents	Expo League		Kingsbury Theater at iO	buy now »
Wed, Jul 2 - Wed, Aug 13	iO Theater presents	Extremely Laugh and Incredibly Jokes	A standup showcase.	iO Theater	buy now »
Wed, Jun 18 - Wed, Jul 23	iO Theater presents	Family	Family is a completely improvised show that follows one family, within one living room, over the course of one day. Our cast of veteran comedians uses inspiration from the audience to generate 60 minutes of side splitting, tear inducing comedy.	Weed Cabaret	buy now »
Thu, Jun 19	VanDuvall & 4rd Productions and iO Theater Presents	The Fest: Vol 1	A new single day BIPOC Comedy Festival: The Fest Vol. 1!	The iO Theater	buy now »
Wed, Jun 18 - Wed, Aug 27	iO Theater Presents	The FREE WEDNESDAY SHOW feat Dumb John and Birdlady	Come be a part of Chicago's most spoiled audience as you are treated to a free performance from iO's premiere long form ensembles: Dumb John, Birdlady, and a special guest team each week. FREE!	The iO Theater	buy now »
Tue, Jun 24	The iO Theater Presents	Fudge and Friends	FUDGE is back for a night of improv with their very good buddies Erin Keif (Hey Riddle Riddle, Win or Lose) and Jesse Kendell (Love Dump). If you love their pod FUDGECAST (formerly Improv is Dead) then you're gonna love this non-podcast show!	iO Theater	buy now »
Wed, Jun 18 - Wed, Dec 17	iO Theater Presents	Green Room - An Improv Jam	A free community networking event designed to give local improvisers from all over the city a weekly opportunity to perform. Bring your own team and sign up for a set!	iO Theater	buy now »
Thu, Jun 26 - Thu, Aug 28	iO Theater presents	Harold Happy Hour	Every Thursday, saddle up with iO house teams Big Deborah, Kismet and Lil Sluggers performing their adapatation of iO's signature longform piece, THE HAROLD.	The iO Theater	buy now »
Sun, Jun 22 - Sun, Jul 20		Harold Night	Using the Harold, an improvised story-telling format, iO's rockstar house teams will showcase the wonderful, strange, and thrilling art of Improv, making you second-guess if what you're seeing is truly made up on-the-spot.	Dayton Cabaret	buy now »
Sat, Jun 21 - Sat, Aug 30	Malarkey Comedy presents	Honk!		Kingsbury Theater at iO	buy now »
Wed, Jul 23	iO Theater presents	HORSEGIRL	A girl. A horse. Something else. This raw, heartfelt, and ridiculously comedic solo show dives into the untamed wilderness of identity. Caught between what we are and what we long to become, one woman explores the mess, beauty, and absurdity of life.	The iO Theater	buy now »
Sat, Jul 12 - Sat, Jul 19	The iO Theater presents	Hot Seat	The 2019 Reader-Recommended show is back featuring some of iO's best players! Hot Seat invites the audience to ask the questions that we're afraid to answer. Get ready for some good old-fashioned truth telling and improv that’s sure to melt your face	The iO Theater	buy now »
Thu, Jul 24	iO Fest 2025	Idiotically Speaking with Chris Kattan	A live performance of the hit podcast featuring Chris Kattan, Joey Nuñez, and Andy Bolduc. , Joey	The iO Theater	buy now »
Thu, Jun 19 - Thu, Sep 25	Malarkey Comedy presents	Improvised DCOM		Kingsbury Theater at iO	buy now »
Sat, Jun 21 - Sat, Jun 28	iO Theater Presents	Improvised Housewives of iO	Saturday’s at 9:30, roll out the pink carpet, because the Improvised Housewives of iO are nipped, tucked and ready to return for their most dramatic season yet.	iO Theater	buy now »
Sat, Jun 21 - Sat, Jul 19	iO Theater Presents	Improvised Jane Austen	Improvised Jane Austen tells a tale, on the spot, in the style of the most beloved 19th-century author. The audience can expect to laugh heartily, wooed to tears, and be made to think on how much, and how little, has changed in 200+ years.	Weed Cabaret	buy now »
Fri, Jun 20 - Fri, Oct 31	iO Theater Presents	Improvised Shakespeare Chicago	The Improvised Shakespeare Company® proudly presents its critically-acclaimed, long-running hit show Improvised Shakespeare Chicago now in it’s 18th year! A brand new Shakespearean masterpiece created right before your very eyes.	Fremont Theater	buy now »
Fri, Jun 20 - Fri, Jul 18	iO Theater Presents	Kohl's Cash: TGIF (That's Good Improv Fridays)	Every Friday iO House Team Kohl's Cash presents a completely original show based on your suggestions.	The iO Theater	buy now »
Tue, Jul 1 - Tue, Jul 29	iO Theater presents	Ladies of Chicago Improv		iO Theater	buy now »
Fri, Jul 25	iO Fest 2025	Ladies Who Ranch	Hailed as an “improper quintet of funny ladies” by the New York Times, “a lady tastic treasure” by Buzzfeed and “demented” by TimeOut NY, the Ladies Who Ranch is a five-person comedy group known for their individual voices.	The iO Theater	buy now »
Sun, Sep 7 - Sun, Sep 28		Late Nite Catechism	presented by Malarkey Comedy	Kingsbury Theater at iO	buy now »
Sun, Jun 22	iO Training Center Presents	Level 1-4 Student Showcase Shows	Come see the culmination of this session's work from our talented student body!	Fremont Theater	buy now »
Sun, Jun 22	iO Training Center Presents	Level 5 Grad Showcases	Come see the culmination of the critically acclaimed iO Training Center during our final showcase performance run.	Fremont Theater	buy now »
Tue, Jun 17 - Tue, Aug 19	iO Theater Presents	Loose Four: A Stand-Up Open Mic	Come sign up and try out your best material at iO's very own open-mic.	iO Theater	buy now »
Mon, Jul 21 - Mon, Aug 18	Malarkey Comedy presents	Magic Mondays	with John Sturk	Kingsbury Theater at iO	buy now »
Sat, Jul 26	iO Fest 2025	Neil Hamburger	“America’s Funnyman” Neil Hamburger has worked every imaginable stage, fromNew York’s Madison Square Garden, to a show in a gorilla cage in an abandoned Catskills zoo.	The iO Theater	buy now »
Wed, Jul 9 - Wed, Sep 10	22 presents	Pandora's Box	A menagerie of improv, comedy and theater	Weed Cabaret	buy now »
Thu, Jun 19 - Thu, Oct 2	iO Theater presents	Phony Award Winning Musical	Chicago's best musical improvisers create a brand new musical in the style of Stephen Sondheim's Company right in front of you!	iO Theater	buy now »
Wed, Jun 18	The iO Theater presents:	SAM: An Existential Comedy Solo Musical	National tour of the award-winning solo musical “SAM”! Hollywood satire! Existential comedy! Meta improv sequences! Broadway parodies! Join Sam Labrecque on a hilarious and heartfelt journey of identity through her pre-successful career as an actor.	The iO Theater	buy now »
Sat, Jul 26	iO Fest 2025	Simple Town	The Sloppy Boys are a “party rock” band from LA consisting of comedians Mike Hanford, Jeff Dutton and Tim Kalpakis. Prior to forming The Sloppy Boys, all three were writer-performers on the sketch comedy show “The Birthday Boys."	The iO Theater	buy now »
Thu, Jun 26 - Thu, Jul 17	iO Theater presents	Sketch Playlist	A weekly all new sketch show.	iO Theater	buy now »
Thu, Jul 24	iO Fest 2025	The Sloppy Boys: Live in Concert 2025	The Sloppy Boys are a “party rock” band from LA consisting of comedians Mike Hanford, Jeff Dutton and Tim Kalpakis. Prior to forming The Sloppy Boys, all three were writer-performers on the sketch comedy show “The Birthday Boys."	The iO Theater	buy now »
Thu, Jun 26 - Thu, Jul 17		Smet Gala Presents Close Quarters	One Location. Endless Fun.	iO Theater	buy now »
Wed, Jun 25 - Wed, Aug 27	iO Theater presents	The Spades Table	A Monthly All-Black Sketch Show	iO Theater	buy now »
Sat, Jun 21	iO Theater presents	Tight Five	A Solo Character Showcase	iO Theater	buy now »
Fri, Jun 20 - Fri, Sep 26	Malarkey Comedy presents	Trapped in a Musical		Kingsbury Theater at iO	buy now »
Fri, Jun 20 - Fri, Jul 18	iO Theater Presents	Voila! The Improvised Musical	The most polished made-up musical strikes every Friday night at iO!	Fremont Theater	buy now »
Sat, Jun 21 - Sat, Jul 19	iO Theater Presents	Whirled News Tonight	Improv ripped right from the headlines! Audience members choose their favorite top news stories of the week this team of experienced improvisers create fast-paced, topical commentary! WSJ Improv Style!	Dayton Cabaret	buy now »
Thu, Aug 7 - Sat, Aug 9		Windy City Comedy Fest	This festival brings together comedians from across the country to celebrate Chicago’s legendary comedy scene. The Windy City Comedy Fest features a weekend of shows at iconic venues, clinics with industry professionals, and networking events.	The iO Theater	buy now »

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