5 Must-See Theater Shows To Check Out In August

CHICAGO — August is traditionally a slow time in the local theater scene, since most companies are gearing up to launch their new seasons in September — or even October.

But the city never rests, and for anyone who can tear themselves away from the beach, stages everywhere still have something to lure you indoors before the end of the summer. Take a look at our five selections below.

Something else you’ll be checking out this month? Let us know at arts@blockclubchi.org.

‘The Outsiders’

Cadillac Palace, 151 W. Randolph, The Loop

Through Aug. 16

It’s the Greasers versus the Socs, again! Set in 1960s Tulsa, author S.E. Hinton’s YA novel about rival teenage gangs — basically, the “haves” and the “have-nots” — became a staple in English classes and a 1983 film directed by Francis Ford Coppola (starring a who’s who of future stars, including Tom Cruise, Rob Lowe, Matt Damon, and Diane Lane). In 2024, a musical version of “The Outsiders” with a book by Chicago native Adam Rapp landed on Broadway. It won four Tony Awards, one of them for Best Musical (Rapp was nominated but didn’t win). This official tour lands in the Loop for a two-week run. Tickets and more info here. 

‘52 Lovers’

Chicago Magic Lounge, 5050 N. Clark St., Uptown

Through Aug. 26

The Chicago Magic Lounge offers a rotating lineup of tricksters performing in its speakeasy-style venue. The August lineup includes renowned Czech magician Ondrej Psenicka, who’s had three hit appearances on “Penn & Teller: Fool Us.” Now he returns to Chicago after a popular Magic Lounge run in 2024. With “52 Lovers,” running every Wednesday night through the end of August, Psenicka blends quirky humor and an uncanny facility with a deck of cards. Tickets and more info here.

‘Adolescent Salvation’

Theater Wit, 1229 W. Belmont Ave., Lakeview

Aug. 14-Oct. 3.

An Iowa native who attended Illinois State University, playwright Tim Venable just moved to Chicago. He was previously based in L.A., which is where this dark comedy made its bold premiere in 2025. The action follows three teenagers who bond and bicker over Taylor Swift, then dabble in danger during one drunken night. The show lands at Theater Wit with the same director as the L.A. version, but a local cast. As one California critic raved: “‘Adolescent Salvation’ is one humdinger of a stunner.” Tickets and more info here.  

‘Living Newspaper Festival’

Jackalope Theatre at the Broadway Armory, 5917 N. Broadway, Edgewater

Aug. 20-24

News and art combine annually in Jackalope’s Living Newspaper Festival, where playwrights turn news stories into bite-sized works of theater. Now in its 17th iteration, the festival is inspired by the Federal Theatre Project of the 1930s. This year’s five short plays (each of them performed every night) take inspiration from a variety of current events, including the proliferation of weight-loss drugs, the long reach of the late Jeffrey Epstein and UFOs. And the talent is impressive: For example, one writer is Ike Holter, whose previous work has been performed on stages from the Steppenwolf to the Kennedy Center. Tickets and more info here. 

‘Ragtime’

Beverly Arts Center, 2407 W. 111th St., Morgan Park/Beverly

Aug. 27-30

Now 30 years old and firmly ensconced in the American musical canon, “Ragtime” is the most renowned musical by the composing team of Stephen Flaherty and Lynn Ahrens. Adapted from the sprawling historical novel by E. L. Doctorow, the show weaves together the experiences of three different demographic groups in early 20th century America — upper-class whites, working-class Blacks and Jewish immigrants. Still a big draw, “Ragtime” just won four Tonys in June for its latest revival. (To find out why, check out Best Actor Joshua Henry and the rest of the cast perform a selection of songs for NPR’s Tiny Desk Concert.) While you’ll have to wait until next year for that production to tour, Beverly Arts Center offers a much quicker hit to soothe your “Ragtime” fix. Tickets and more info here.