Lookingglass Theatre reprises “Lookingglass Alice,” the ensemble’s stunning, circus-infused adaptation of Lewis Carroll’s “Alice in Wonderland.” Adapted and directed by David Catlin and featuring Molly Hernandez, Lindsey Noel Whiting, Kareem Bandealy, Adeoye, Michel Rodriguez Cintra and Samuel Taylor. For ages 5+. From April 30-July 31 at Lookingglass Theatre, 821 N. Michigan. Tickets: $45-$65. Visit lookingglasstheatre.org.
- Steppenwolf Theatre inaugurates its new in-the-round theater with Yasen Peyankov’s funny and lyrical adaptation of Anton Chekhov’s “Seagull.” On a long summer weekend at a Russian country estate, three generations collide as they examine questions that haunt the intellectual artist class. The cast features ensemble members Jeff Perry, Sandra Marquez, Caroline Neff, Karen Rodriguez, Eric Simonson and Namir Smallwood, alongside Keith Kupferer, Elijah Newman, Jon Hudson Odom, Joey Slotnick and Lusia Strus. (Scott Jaeck steps in for Jeff Perry for performances May 24–June 5.) From April 28-June 12 at Steppenwolf Theatre, 1650 N. Halsted. Tickets: $20-$88. Visit steppenwolf.org.
- Comedian and storyteller Mike Birbiglia comes to town with his one-man show “The Old Man and the Pool,” a coming-of-age tale of life, death and a highly chlorinated YMCA pool. Birbiglia has been working on the show for three years and the Chicago audience will be one of the first to see it formed into a single evening of theater. Seth Barrish directs. From April 28-May 22 at Steppenwolf Theatre, 1650 N. Halsted. Tickets: $55-$75. Visit steppenwolf.org.
- Raven Theatre concludes its season with Melissa Ross’ “The Luckiest,” a comedy-drama that explores how we choose to take ownership of our lives. When Lissette (Cassidy Slaughter-Mason) is diagnosed with a serious illness, she finds herself at odds with her best friend Peter (Christopher Wayland) and her mother Cheryl (Tara Mallen). Cody Estle directs. From May 4-June 19 at Raven Theatre, 6157 N. Clark. Tickets: $40. Visit raventheatre.com.
- The Gift Theatre presents Naomi Iizuka’s “At the Vanishing Point,” which weaves together historical fact, myth and memory to ask the question: How do we remember a part of our history at the moment that it’s slipping away? Directed by Lavina Jadhwani. From April 28-May 22 at Filament Theatre, 4041 N. Milwaukee. Tickets: $40-$50. Visit thegifttheatre.org.
- The Neo-Futurists return to live performances with “Wildcats,” a multimedia drag spectacle exploring themes of loneliness and isolation via the true story of Lucille Ball’s disastrous Broadway debut in 1960. Created by ensemble members Ida Cuttler and Nick Hart. Halena Kays directs. From May 2-28 at The Neo-Futurist Theater, 5153 N. Ashland. Tickets: $10. Visit neofuturists.org.
- Tony Award-winning “Jersey Boys” is the musical that goes behind the music and inside the story of Frankie Valli and the Four Seasons. From May 3-8 at Cadillac Palace Theatre, 151 W. Randolph. Tickets: $31+. Visit broadwayinchicago.com.
- The Artistic Home presents “The Pavilion,” Craig Wright’s drama about two former high school sweethearts who are thrust back together when they attend a school reunion. Kristin Collins, John Mossman and Todd Wojcik star; Julian Hester directs. From April 30-June 5 at The Den Theatre, 1331 N. Milwaukee. Tickets: $35. Visit thedentheatre.com.
- Buffalo Theatre Ensemble stages Mat Smart’s “Naperville,” a drama, set in a coffee shop, about how community can add to your life. Directed by Kurt Naebig. From April 28-May 29 at McAninch Arts Center, 425 Fawell, Glen Ellyn. Tickets: $42. Visit atthemac.org.
- “Collected Stories” is Donald Margulies’ drama about a prominent author who mentors a student until the younger writer finds success with a story that’s all too familiar. Directed by Ted Hoerl. From April 28-June 5 at Redtwist Theatre, 1044 W. Bryn Mawr. Tickets: $35. Visit redtwisttheatre.org.
- “Shout! The Mod Musical” is a tribute to the dynamic singers of the ’60s including Dusty Springfield, Petula Clark, Cilla Black and more. From April 28-June 11 at Metropolis Performing Arts Center, 111 W. Campbell, Arlington Heights. Tickets: $40. Visit metropolisarts.com.
- “Emancipation” is the second installment in a trilogy composed by Adrian Dunn exploring Black life in America through genres created by Black Americans. “My inspiration for this piece includes Black sacred texts of Maya Angelou, Kanye West, Tupac, Marlon Riggs, James Baldwin and Audre Lorde, to name a few,” says Dunn. The program is performed by The Adrian Dunn Singers and Rize Orchestra at 7:30 p.m. April 29 at Harris Theater, 205 E. Randolph. Tickets: $20-$140. At 2 p.m. April 30, there’s a 60-minute performance ($10, $15) for children and families featuring excerpts from the piece. Visit harristheaterchicago.org.
- With her distinctive singing style — stripped-down, folky but also forceful and cerebral—Aimee Mann has long explored psychological themes with a dark wit. She began developing the music on her new album, “Queens of the Summer Hotel,” in 2018 when she agreed to write songs for a stage adaptation of “Girl Interrupted,” Susannah Kaysen’s memoir about her stay in a psychiatric hospital in the 1960s. The online music site Holler says, “Three decades into her solo career, Aimee Mann still manages to surprise and delight.” At 8 p.m. April 29-30 at Old Town School of Folk Music, 4544 N. Lincoln. Tickets: $75. Visit oldtownschool.org.
- Celebrate the birthday of Chicago bluesman Wayne Baker Brooks with a music-filled bash at Buddy Guy’s Legends, 700 S. Wabash, on April 30. The lineup includes a free acoustic set starting at 5:30 p.m., followed by openers Big Lew & The Crew at 9 p.m., and Brooks starting at 10:30 p.m. (tickets required for openers/Brooks performances). Tickets, $25. Visit etix.com.
- While the new album “angel in realtime” from Australian indie-rock band Gang of Youths is eclectic in its influences, ranging from American minimalism to Britpop, it’s equally rooted in frontman David Le’aupepe’s Samoan heritage with samples of indigenous music from the Polynesian islands and the wider South Pacific. Casual Male opens at 8 p.m. May 3 at Metro, 3730 N. Clark. Tickets: $27.50, $30. Visit metrochicago.com.
- “The Sandra Delgado Experience” is the actor-singer’s big band event with singing, dancing and storytelling. The performance is inspired by the Colombian music that has shaped Delgado and the songs that helped her through the pandemic ranging from Colombian cumbias to English-language indie sounds. At 7 p.m. May 1 at Joe’s on Weed Street, 940 W. Weed. Tickets: $35. Visit sandradelgado.net.
- “Haskell Wexler Centennial: Impact, Influence and Iconography” features eight films by the groundbreaking cinematographer. A cinematic trailblazer, he worked with directors including Norman Jewison, Hal Ashby, John Sayles, Milos Forman and John Cassavetes, and pioneered new techniques such as the Steadicam. The films screened are “One Flew Over the Cuckoo’s Nest,” “The Thomas Crown Affair,” “Medium Cool,” “Bound for Glory,” “In the Heat of the Night,” “Faces,” “Matewan” and “The Conversation.” “Medium Cool,” on which Wexler served as director and cinematographer, is set during the real-life upheaval of the 1968 Democratic National Convention and remains an iconic Chicago film. From May 4-28 at Gene Siskel Film Center, 164 N. State. Tickets: $12. Visit siskelfilmcenter.org.
Museums & Galleries
- “Key Change” is a new exhibit that addresses the present-day housing crisis and proposes alternative solutions in urban living. Artists Gabrielle Garland, Tonika Lewis Johnson, Maymay Jumsai, Riff Studio and South Side Home Movie Project present their interpretation of the topic via painting, collage, sculpture, video and large-scale installation. From April 29-July 16 at Weinberg/Newton Gallery, 688 N. Milwaukee. Admission is free. Visit weinbergnewtongallery.com.
- The One of a Kind Show returns for its annual spring market featuring more than 300 vendors from across the country selling everything from fine art to jewelry, clothes, photography, furniture and so much more. There’s also live music, hands-on workshops and gourmet cafes. From April 29-May 1 at The Mart, 222 W. Merchandise Mart Plaza. Admission: $10. Visit oneofakindshowchicago.com.
- Check out four of the most famous and valuable United States coins, including a $7.5 million nickel and a $2 million dime, at the Central States Numismatic Society Convention. Hundreds of dealers will be buying and selling with the public, plus there are dozens of educational exhibits of rare coins and paper money. From April 28-30 at the Renaissance Hotel, 1551 Thoreau, Schaumburg. Admission: $5. Visit centralstatesnumismaticsociety.org/convention.
- Elmhurst’s annual art festival, Art in Wilder Park, takes place April 30-May 1 at 175 S. Cottage Hill. Featured are artists selling jewelry, paintings, ceramics, prints, fiber arts and more. Plus, musical acts, food vendors and a children’s activity area. Admission is free. Visit elmhurstartmuseum.org/events.
- Shop for treats for mom at the Ravenswood Mother’s Day Market, which offers a variety of handmade jewelry, artwork, baked goods, skincare products and more. Plus, make something original during kid-friendly craft activities led by Lillstreet Art Center. From 10 a.m.-4 p.m. April 30 at Ainslie Arts Plaza, 4836 N. Lincoln. Free. Visit ravenswoodchicago.org.