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Your Expert Fall Theater Guide

Posted on September 29, 2025   |   Updated on September 30, 2025
Emily Mack

Emily Mack

"Ashland Avenue” at Goodman Theatre

The warm set of “Ashland Avenue,” on now at Goodman Theatre. (Courtesy of Todd Rosenberg / Goodman Theatre)

As fall theater season picks up across Chicago, we sat down with veteran actor — and current “Big White Fog” star — Ronald Conner for tips.

We’ve also sprinkled in a few recs of our own 😉

City Cast

Why Are You Sleeping On Chicago Theater?

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“Big White Fog” at Court Theatre

📅 Runs through Oct. 12


This near-century-old play by Theodore Ward follows a Black family in Chicago during Marcus Garvey’s “Back-to-Africa” movement. “Given the unrest in the country right now … it's the perfect time to do the play, and we have to,” Conner says.

“Ashland Avenue” at Goodman Theatre

📅 Runs through Oct. 18


Come to see a big TV star, stay for the gorgeously homey set — and lots of old-school Chicago wisecracks. This play stars Jenna Fischer (aka Pam from “The Office”) and Chicago's own Francis Guinan as a daughter and father debating the fate of their family electronics store.

“Rome Sweet Rome” at Chicago Shakespeare Theater

📅 Runs through Oct. 18


This adaptation of Julius Caesar by the Q Brothers is a “hip hop-era,” blending the Bard with more modern rhythms. The theater is ”one of the most beautiful” in the city, according to Conner, and I concur. Don’t sleep on it just ‘cause it’s at Navy Pier!

“Veal” at Red Orchard Theatre

📅 Runs through Nov. 5


This one’s dystopian, but that’s not the scary part. In “Veal,” a young woman named Chelsea becomes Queen of North America following a massive coup — then is confronted by three ex-friends from middle school who make her revisit those painful years.

Other Theater Tips

It’s OK to React!

Overall, audience members should feel comfortable reacting to the play. “It's OK to respond,” Conner says.

He’s noticed that in audiences of mixed cultures, people are hesitant to laugh, especially during culturally specific plays. But even if people mean well, Conner says, the audiences’ audible reactions feed the performers.

“Man, when people are reacting and you can hear ‘em … hearty laughs … we’re going,” Conner says. He calls that kind of energy “electric.”

Get in the Know

Chicago has over 200 theaters, and they’re more accessible than people realize. Neighborhood theaters are often more affordable.

Places to check out you may not have heard of:

🎭 Check out even more ongoing shows!

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