Theater
Jackalope Theatre presents “The Singularity Play,” Jay Stull’s existential comedy/sci-fi horror story about a theater troupe that gathers to rehearse a new play written by an advanced AI named “Denise.” Artistic director Kaiser Ahmed says the show will “transport audiences to the edges of their imagination.” Georgette Verdin directs. From May 19-June 22 at Berger Park, 6205 N. Sheridan. Tickets: $15-$35. Visit jackalopetheatre.org.
“The Prodigal Daughter” is the final installment of Joshua Allen’s Grand Boulevard Trilogy, three plays about Black families in Chicago in the early 20th century with each story set on a different floor of a South Side apartment building. In the final play, Virginia Bass (Stephanie Mattos), a successful saleswoman, pays her hometown a visit, which leaves her wondering if you truly can go home again. Jerrell L. Henderson directs. From May 16-June 23 at Raven Theatre, 6157 N. Clark. Tickets: $35-$45. Visit raventheatre.com.
“Beetlejuice: The Musical” is an adaptation of Tim Burton’s film about an unusual teenager whose life changes when she moves with her family into a house haunted by a dead couple and a double-crossing demon. From May 21-26 at Nederlander Theatre, 24 W. Randolph. Tickets: $49+. broadwayinchicago.com.
The concert experience “Rain: A Tribute to the Beatles” celebrates the timeless music of the Fab Four with performances of favorite hits for fans old and new. At 7:30 p.m. May 17, 2 and 7:30 p.m. May 18 at CIBC Theatre, 18 W. Monroe. Tickets: $41+. Visit broadwayinchicago.com.
Pop Up! Productions presents Tom Kitt and Brian Yorkey’s musical “Next to Normal,” which explores how one suburban household copes with crisis and mental illness. Director Hershey Kaur Suri reimagines the story through the lens of a South Asian family living in the Chicago suburbs. From May 17-26 at South Asia Institute, 1925 S. Michigan. Tickets: $35-$55. Visit saichicago.org.
First Floor Theatre stages Brynne Frauenhoffer’s “Pro-Am,” a drama set in Miami’s professional-amateur porn scene where a rising star and a driven trans performer are determined to change things. Rebecca Willingham directs. From May 16-June 15 at The Den Theatre, 1331 N. Milwaukee. Tickets: $5-$35. Visit firstfloortheatre.com.
The Conspirators present “Viva la Mort,” Sid Feldman’s musical about an aging pop icon who returns to her hometown and to her just-as-aging ex. Wm. Bullion directs. From May 16-June 9 at Otherworld Theatre, 3914 N. Clark. Tickets: $25. Visit conspirewithus.org.
Three Crows Theatre presents “The Danish Play,” Sonny Mills’ account of their great-aunt’s true story of resistance and survival during World War II and in the years after. Kirstin Franklin directs. From May 16-June 16 at Raven Theatre, 6157 N. Clark. Tickets: Free-$50. Visit raventheatre.com.
A group of scouts on their way to the renowned Philmont Camp encounter a disaster and only they can save themselves in “Tiny Fascists: A Boy Scout Musical.” Mick Napier directs. From May 17-June 28 at The Annoyance Theater, 851 W. Belmont. Tickets: $20. Visit theannoyance.com.
Magician David Williamson presents his new act “Ridiculous!,” a blend of mind-bending illusions, comedy and a dash of anarchy. From May 16-June 30 at The Rhapsody Theater, 1328 W. Morse. Tickets: $20+. Visit rhapsodytheater.com.
Dance
Hubbard Street Dance ends its season with performances of Johan Inger’s “IMPASSE” (a company premiere), Aszure Barton’s “A Duo,” Kyle Abraham’s “Show Pony” and Maria Torres’ “Echoes of Our Ancestors.” From May 17-19 at Harris Theater, 205 E. Randolph. Tickets: $15-$110. Visit hubbardstreetdance.com.
Cerqua Rivera Dance Theatre, a multicultural collective of artists, celebrates its 25th season with a program featuring Wilfredo Rivera and Joe Cerqua’s “American Catracho,” Katlin Bourgeois and James Sanders’ “From Here to Home,” Rivera’s “Lagrimas Negras,” Bourgeois’ “Tether,” Shannon Alvis’ “The Sea” and Michelle Manzanales’ “The Island.” At 7:30 p.m. May 17-18 and 3 p.m. May 19 at Ruth Page Center for the Arts, 1016 N. Dearborn. Tickets: $40-$60. Visit cerquarivera.org.
Music
Megan Thee Stallion brings her Hot Girl Summer Tour to town for two explosive nights of rap. Her most recent album, “Traumazine,” was released in 2022, but in recent months she’s dropped the new singles “Cobra,” “Not My Fault” and “Hiss,” which are sure to be performed on this, her first headlining arena tour. Memphis-born rapper GloRilla opens at 7 p.m. May 17, 19 at United Center, 1901 W. Madison. Tickets: $55+. Visit ticketmaster.com.
Grammy-winning musician, producer, composer and Blue Note Records president Don Was introduces his new group The Pan-Detroit Ensemble, which is made up of jazz musicians from his hometown. They’ll perform a mix of new originals; interpretations of songs written by artists like Yusef Lateef, Olu Dara and Henry Threadgill, and updated cuts from albums that Don recorded with his Orquestra Was and Was (Not Was). At 7 and 9:30 p.m. May 22 at Space, 1245 Chicago, Evanston. Tickets: $35-$45. Visit evanstonspace.com.
Ann and Nancy Wilson, the sisters who front the legendary rock band Heart, had a falling-out and haven’t performed together since 2019. But they have since reconciled and are on the road for what promises to their usual thrilling live show filled with classic tunes. At 8 p.m. May 17 at Allstate Arena, 6920 N. Mannheim. Tickets: $35+. Visit ticketmaster.com.
The Decemberists offer a preview of new songs on their album “As It Ever Was, So It Will Be Again,” due out June 14. The bandmates’ ninth studio effort is a double album split into “four thematic sides of hyperliterate folk-rock that is their most empathetic and accessible music to date.” At 7:30 p.m. May 21 at The Salt Shed, 1357 N. Elston. Tickets: $85+. Visit ticketmaster.com.
Step into the 1970s underground music scene as actress-singer Bethany Thomas embodies the many identities of the iconic Lou Reed when, backed by a six-piece band, she offers her take on his seminal rock album “Transformer.” At 8:30 p.m. May 22-24 at Constellation, 3111 N. Western. Tickets: $35, livestream $5. Visit constellation-chicago.com.
Singer-songwriter Katie Pruitt tours behind her new album, “Mantras,” which showcases her “soulful powerhouse of a voice.” At 8 p.m. May 17 at Thalia Hall, 1807 S. Allport. Tickets: $22-$32. Visit thaliahallchicago.com.
Milwaukee Metalfest features more than 70 bands from around the world. From May 16-19 at The Rave/Eagles Club, 2401 W. Wisconsin, Milwaukee. Tickets: $79-$119. Visit milwaukeemetalfestival.com.
Museums
“Designing for Change: Chicago Protest Art in the 1960s-70s” takes visitors back to a pivotal time in local and U.S. history via posters, fliers, signs, banners, newspapers, magazines and books. Also featured are period photography, first-person interviews and works by a new generation of “artivisits” who are carrying on the city’s legacy of protest art. From May 18-May 4, 2025, at Chicago History Museum, 1601 N. Clark. Admission: $17, $19, Illinois residents 18 and under free. Visit chicagohistory.org.
“What Is Seen and Unseen: Mapping South Asian American Art in Chicago” is the first comprehensive exhibition to map and disseminate the history of South Asian art and artists in Chicago. Included are an archival exhibit of more than 125 years of cultural history and an exhibit of works by eight contemporary artists. From May 18-Oct. 26 at South Asia Institute, 1925 S. Michigan. Admission: $10. Visit saichicago.org.
Movies
Asian American Showcase, a series featuring new work by emerging filmmakers, opens with Sean Wang’s Sundance hit “Didi,” the story of an impressionable 13-year-old Taiwanese American boy who learns what his family can’t teach him: how to skate, how to flirt and how to love your mom. Also featured are Kenji Tsukamoto’s “Ashima,” Fawzia Mirza’s “The Queen of My Dreams,” So Young Shelly Yo’s “Smoking Tigers” and several programs of short films. From May 17-23 at Gene Siskel Film Center, 164 N. State. Tickets: $13, $30 for five films. Visit siskelfilmcenter.org.
Family Fun
Chocolate Fest is Long Grove’s annual salute to everything chocolate including foods, drinks and chocolate experiences such as pairings with wine and candy-making demonstrations. Plus music and children’s activities. From noon-11 p.m. May 17, 10 a.m.-11 p.m. May 18 and 10 a.m.-6 p.m. May 19 in downtown Long Grove, 145 Old McHenry Rd. Admission is free. Visit longgrove.org.
The summer festival/art fair season gets underway with the Lincoln Roscoe Art & Craft Fair, which features a wide array of artists and their wares, painting classes, music, food, children’s activities and more. From 10 a.m.-7 p.m. May 18 and 10 a.m.-5 p.m. May 19 on Lincoln from School to Roscoe. Admission is free. Visit amdurproductions.com.
For a prehistoric adventure, check out “Dinos Alive,” an immersive experience where you’ll meet more than 80 life-sized, moving animatronic dinosaurs in their natural Jurassic habitat. Opens May 21 at Exhibition Hub Art Center, 2367 W. Logan Blvd. Tickets: $20.90. Visit dinosaliveexhibit.com/chicago/.
Spring Fun Fest invites families to enjoy outdoor activities including bounce houses, balloon sculptors, face painting, a petting zoo and music by Jeanie B. and the Jelly Beans. From 1-5 p.m. May 19 at Parkway Bank Park, 5501 Park Place, Rosemont. Visit rosemont.com/thepark/.
