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Traveling Just For Trips And Giggles

What’s so funny? These top-shelf comedy experiences, all just a road trip away.
the exterior of The Second City is on the comedy club tour

The Second City in Chicago.

INDIANAPOLIS does not want for chortling. You have Helium Comedy Club downtown, Avon’s Red Curb Comedy—and your next neighborhood association meeting. But once you’ve been there, done those, wit and sarcasm beckon just a little farther afield. 

The biggest name in Midwest comedy is The Second City (312-337-3992, Its flagship Chicago theater has been a launching pad for funny folks the likes of Joan Rivers, Alan Arkin, Keegan-Michael Key, and Tina Fey. Haven’t heard of the current company members? Just wait. A few will surely find their way to SNL or movie fame.

Queer Eye parody troupe at The Second City

Queer Eye: The Musical Parody cast members (from left) Eddie Ledford, Evan Starkweather, Dominic Rescigno, Evan Tyrone Martin, and Tina Arfaee.Photo by Timothy M. Schmidt

Unlike traditional comedy clubs, a Second City show consists primarily of sketches developed out of earlier improvisations. The current show, Do The Right Thing, No Worries If Not, is its 110th and includes belly-laugh bits on TikTok dancing, the U.S. Senate, and a comparison of dinosaurs and gynecologists. Order drinks and small bites to enjoy in your seat (just don’t chuckle with your mouth full.) Second City also offers Best Of revues, plus its often-edgier E.T.C. company performances, which include Clued In, an improvised murder mystery, and a Queer Eye musical parody.

Flyover Comedy Festival

Rachel Feinstein headling the 2021 Flyover Comedy Festival in Seattle. Photo by Rustin McCann

You can catch a Second City show seven days a week, but you’ll need to plan for St. Louis’s Flyover Comedy Festival ( November 10–12. Most of the 50 acts are in walking distance of each other in The Grove, a buzzy nabe known for craft beer and barbecue. Headliners will include Sarah Silverman and Ron Funches, but Flyover was a crowd-pleaser before big names signed on. “The first year, 2017, I didn’t know how it was going to go,” recalls producer Zach Gzehoviak. “I said, ‘Please, let there be 10 people.’ The rooms were full. St. Louis showed up … and continued to show up.” 


MINGLE in Chi-Town Stick around Second City for the Saturday After Hours improv set, then grab a drink at one of the best dive bars in America, The Old Town Ale House ( You may run into cast members while marveling at the wild artwork and legendary jukebox. 

SAVOR St. Louis. Consider the Flyover three-day wristband. Between shows, fill up on the succulent smoked-meat sandwiches at Beast Butcher & Block (


SKIMP on gas, not the good times. Head down to Bloomington’s The Comedy Attic (, opened in 2008 as part of the Funny Bone chain. The savvy owners soon took it independent, and a national reputation for excellence ensued. Upcoming shows include a weekend with Beth Stelling. Catch her stand-up special, Girl Daddy, on HBO Max. 


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