Preview: Chicago’s iO Fest Returns with Star-Studded Lineup July 24–27

Chicago’s rich improv tradition takes center stage next week as iO Fest 2025 returns July 24-27 to the iO Theater, 1501 N. Kingsbury St., filling four days with comedic performances, workshops and special events..

Homegrown Chicago talent and nationally recognized headliners will showcase this year’s fest. Audiences can expect an eclectic blend of long-form improv, sharp sketch comedy, stand-up, experimental shows, and even live podcast recordings. It’s a unique opportunity to experience the creativity and spontaneity that have made Chicago a global leader in comedy.

From left: Jeff Dutton, Tim Kalpakis, and Mike Hanford of The Sloppy Boys. Photo by Carter Wright

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Featured performers include: Neil Hamburger, the legendary “America’s Funnyman” with his one-of-a-kind challenge to audience humor. The Sloppy Boys, an uproarious party-rock trio blending music and laughs. Idiotically Speaking with Chris Kattan, a variety show featuring the former SNL cast member. Plus the legendary Bear Down Podcast, making its first live appearance in more than a decade, with an exclusive, one-night-only taping.

Chicago favorite 3Peat will also take the stage, alongside 2 Square (John Lutz and Peter Grosz), Simple Town, BATSU!, Ladies Who Ranch, Messing with Lehr, and, making Willy proud, the beloved Improvised Shakespeare Chicago, now in its 18th year.

From left: Lisa Beasley, Patrick Rowland, Nnamdi Ngwe, Dewayne Perkins, Allison Blair. Photo courtesy of iO Theater

Beyond the headliners, iO Fest showcases a wide array of house teams that represent the diversity and innovation of Chicago’s improv community. Performances from groups such as Deep Schwa, Devil’s Daughter, Birdlady, Dumb John, Whimsy Lohan and The Armando Diaz Experience will be featured, along with many other ensembles.

iO Fest will also offer a series of workshops designed to help all levels of improvisers refine their skills. These sessions cover everything from classic long-form techniques to on-camera comedy direction and dynamic approaches for scene work, providing a unique opportunity to learn directly from some of the most experienced instructors in comedy.

All events will take place at the iO Theater, with multiple stages hosting back-to-back shows each day. See the full schedule at ioimprov.com/io-fest, and follow iO on social media for festival updates, behind-the-scenes looks and more.

Tumpale Mwakasisi