Five Chicago arts picks: Steppenwolf’s 'Windfall,' 'Gatsby' musical, Kyiv–Chicago exhibit, and more

Chicago’s cultural calendar is packed this week, from a new Steppenwolf drama probing grief and money to a touring musical of The Great Gatsby, a Ukrainian American art showcase linking Kyiv and Chicago, a milestone exhibit at the Chicago Architecture Center, and a reunion concert built around a cult-favorite TV series.

At Steppenwolf Theatre, “Windfall” examines cash-based anxieties, trauma and life-altering choices. Written by Steppenwolf ensemble member and Academy Award-winning playwright Tarell Alvin McCraney, the play follows a Chicago father whose child dies in a clash with police.

He is told to take the city’s cash settlement and move away, prompting a wrenching decision about whether to leave the place he’s called home or remain with his grief. The production is running now through May 31. The classic F. Scott Fitzgerald novel gets the musical treatment at the Cadillac Palace Theatre.

Premiered in 2023 at New Jersey’s Paper Mill Playhouse, The Great Gatsby has had stints on Broadway, in London and in Seoul, and is now embarking on a North American tour. Its Chicago engagement runs from April 21 through May 3. At the Ukrainian National Museum, “9025 km” takes its name from the approximate distance between Chicago and Kyiv.

The exhibition presents work by 12 Ukrainian American artists from Chicago who explore how the two sister cities are, in their words, “united by shared spirit and resilience.” The show opened April 8 and runs through April 30; an opening event with several featured artists is scheduled for April 17.

The Chicago Architecture Center marks a milestone with “Currents: 60 Years of the Chicago Architecture Center.” Founded in 1966, the CAC has long highlighted the city’s design heritage through volunteer-led tours, a river cruise and educational programs. The anniversary exhibit opens in April and runs until May 1.

Rounding out the week, “Crazy Ex-Girlfriend: The 10 (ish) Year Reunion Concert” brings the hit TV series back to the stage. Led by Emmy winner Rachel Bloom, the concert is set for Sunday, April 19 at the Chicago Theatre, revisiting songs and moments from the show’s 2015–2019 run on the CW.

Taken together, these events spotlight the breadth of Chicago’s arts scene—its storied institutions, its touring spectacles and its neighborhoods, including Ukrainian Village, which was initially populated by German immigrants in the mid-19th century and later shaped by Ukrainian immigrants and refugees.

This week’s offerings underscore the city’s enduring creative energy and community resilience.