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Sandra Delgado
Photograph: Joe Mazza/Brave Lux

1 Are You Experienced?

If you haven’t had The Sandra Delgado Experience, now’s your chance: Delgado, an actor and playwright, reunites with Carpacho y Su Super Combo, the house band from her hit 2018 play La Havana Madrid, for this cabaret-style concert. May 1.

Nick Cave Soundsuit
Photograph: Nick Cave and Jack Shainman Gallery

2 Cave of Wonders

Opening at the Museum of Contemporary Art, Nick Cave: Forothermore is the Chicago-based artist’s first career retrospective, featuring immersive installations and more than a dozen of Cave’s signature Soundsuits. May 14–Oct. 2.

3 Scout’s Honor

Aaron Sorkin’s 2018 stage adaptation of Harper Lee’s classic To Kill a Mockingbird claims the record as the highest-grossing American play in Broadway history. The touring cast visiting the Nederlander is led by Richard Thomas as Atticus Finch. May 17–29.

4 Public Interest

The theme for the Chicago Humanities Festival’s spring edition is “Public,” and the lineup of speakers suggests a broad definition, with headliners ranging from Anita Hill to John Waters. May 1–22.

5 Keeping the Beat

Jazz drummer Tommaso Moretti celebrates the release of his latest album, Inside Out, with a live show at Constellation. May 20.

6 Rebel Sell

A longtime rite of Chicago spring, the outdoor market Renegade Craft Fair comes to Andersonville for the first time, taking over nearly a mile-long stretch of Clark Street between Foster and Edgewater Avenues. May 21–22.

Photograph: Mat Hayward/Getty Images

7 Home Turf

Rapper Saba’s Back Home Tour will never be more aptly named than when the West Side native plays the Byline Bank Aragon Ballroom. May 5.

Photograph: Vin Reed

8 Lace ’Em Up

In previews at the Royal George when the pandemic hit, the new roller-rink musical Skates — starring American Idol power couple Diana DeGarmo and Ace Young — now inaugurates the newly renovated Studebaker Theater. May 24–Aug. 28.

Sasheer Zamata
Photograph: Gersh Comedy

9 Comics Shop

SNL alum Sasheer Zamata is the latest cool-kid comedian to visit Wicker Park’s Den Theatre, an increasingly popular venue for touring standups. May 7.

10 Dreams Come True

The newest music fest on Chicago’s calendar, Sueños brings a lineup of Latin stars — including headliners J Balvin and Ozuna — to a single Grant Park stage. May 28–29.