A son lost in a clash with the police. A huge cash settlement on the table. And a father torn between staying put in Chicago or starting anew. That all-too-real dilemma is what underpins the play “Windfall,” a new work written by Oscar-winning Steppenwolf ensemble member Tarell Alvin McCraney.

Every Thursday, WTTW News newsletter producer Josh Terry highlights his picks for the week’s must-see cultural events.

Every Thursday, WTTW News newsletter producer Josh Terry highlights his picks for the week’s must-see cultural events.

The former journalist, who was awarded the National Medal of Arts by President Joe Biden in 2024 for his contributions as an arts leader in Chicago, died at his home Sunday following a brief battle with cancer.

Chicago arts are deeply rooted, part of the city’s DNA, and they aren’t as moveable as a football team. Here are this week’s cultural points of interest, taking you from the South Loop to the North Side to Arlington Heights.

From the semi-obvious to the semi-obscure, a roundup of Chicago-area arts recommendations awaits.

Here’s a soulful and sometimes silly six-pack of the artistic and the fantastic — our shortlist of Chicago shows to kick-start your heart and make your brain buzz.

Michael Madsen, whose menacing characters in “Reservoir Dogs” and “Kill Bill” made him a standout in Quentin Tarantino’s films, has died.

If you can’t “get out of town,” as the Cole Porter song says, at least get out of your house or apartment. Start the second half of 2025 on sure footing — see something, do something.

Steppenwolf Theatre’s “You Will Get Sick” is laugh-out-loud funny and deadly serious. It’s a puzzle of a play where the pieces come together in surreal but satisfying ways.

Whether the weather ahead is pleasant or there’s a June monsoon brewing, here’s a starter list of arts and culture opportunities to get you out into the atmosphere.

Branden Jacobs-Jenkins’ “Purpose” won best play, and Kara Young took home the award for best performance by and actress in a featured role for the production that first opened in Chicago in 2024. The play moved to Broadway and is running in New York through Aug. 31, 2025.

Whether it’s a musical on the “Queen of Rock’n’Roll,” an esoteric screening of VHS oddities, or two imaginative plays, you have a lot of stellar options to explore Chicago’s thriving cultural scene.

Here are the early blooms of the spring arts season. Make a bouquet and share them with someone you love. National Public Housing Museum Grand Opening – 919 S. Ada St.

Take a seat in Steppenwolf’s mainstage theater and enter the world of “Fool for Love,” Sam Shepard’s 75-minute play dating from 1983.

Steppenwolf Theatre commissioned a powerful new play receiving the strongest reviews of the summer on the Chicago stage. “Little Bear Ridge Road” stars Laurie Metcalf in her return to Steppenwolf after a 14-year absence.