18 things to do in Chicago May 21-27

Theater

Toccara Castleman (left) and Jasmine Robertson of "Gee's Bend" with  mural by Sarah Kaiser in the background

Toccara Castleman (left) and Jasmine Robertson of “Gee’s Bend.”

Tuesdai B. Perry

  • Fleetwood-Jourdain Theatre presents “Gee’s Bend,” Elyzabeth Gregory Wilder’s play that follows a family from 1939-2002 as they experience segregation, family strife, the Civil Rights Movement and celebrity. The play is set in the real-life Alabama community of Gee’s Bend, which has become known for the hand-stitched quilts made by generations of women who grew up there. Tim Rhoze directs. From May 23-June 7 at Noyes Cultural Arts Center, 927 Noyes St., Evanston. Tickets: $33. Visit fjtheatre.com.
  • Blue Demon Theatre stages “Company,” Stephen Sondheim and George Furth’s musical comedy about a man who contemplates his single life leading him to examine marriage, his relationships and his life. Sydney Sallman directs. From May 22-24 at Greenhouse Theater, 2257 N. Lincoln Ave. Tickets: $11, $22. Visit greenhousetheater.org.
  • Boston-based Cunning Folk Theatre comes to town with its production of “Stories,” which follows a young Jewish storyteller in 1898 Warsaw as he tries to write a story that will intrigue a woman who he is definitely (he tells himself) not in love with. From May 27-31 at Athenaeum Center, 2936 N. Southport Ave. Tickets: $24, $29. Visit athenaeumcenter.org.

Dance

  • Chicago Movement Collective and Winifred Haun & Dancers present “Persistent Spring,” an annual event showcasing new works by Rachel Walker, Steven Hou, Imani English, Faith von Atzigen, Winifred Haun, Valerie Lowder and more. At 7 p.m. May 22 at Ruth Page Center for the Arts, 1016 N. Dearborn St. Tickets: $39. Visit winifredhaun.org.

Music

A$AP Rocky performs at Lollapalooza 2025

A$AP Rocky performs at the Bud Light stage Sunday, Day 4 of Lollapalooza. The rapper returns to Chicago for his show on May 27 at United Center.

Candace Dane Chambers/Sun-Times file

  • It seems that in recent years rapper A$AP Rocky has been more focused on acting (“Highest 2 Lowest,” “If I Had Legs I’d Kick You”) and fashion (the Met Gala, brand ambassador for Chanel). Now in 2026 it’s back to his music roots with an album of new material, “Don’t Be Dumb,” his first full-length release in eight years, and a return to the arena stage for a 20-city tour that kicks off in Chicago. At 7:30 p.m. May 27 at United Center, 1901 W. Madison St. Tickets: $95+. Visit ticketmaster.com.
  • The annual Suenos Music Festival, among the nation’s largest gathering of Latin artists, features performances by J Balvin, Kali Uchis, Fuerza Regida, Danny Ocean, Manuel Turizo, Yandel Sinfonico, Ryan Castro, Tito El Bambino, Paulo Londra, Chino Pacas and many more. From noon-10 p.m. May 23-24 in Grant Park, main entrance at Ida B. Wells and Columbus Drives. Tickets: $189+. Visit suenosmusicfestival.com.

Chris Greene Quartet

Chris Greene Quartet is celebrating the release of “Conversance,” the first jazz album released by Pravda Records.

Ozzie Ramsay

  • The Chris Greene Quartet has been together for 21 years thus explaining their unique jazz chemistry. Led by Evanston native Greene, the ensemble also includes Damian Espinosa (piano), Marc Piane (bass) and Steve Corley (drums). The band is celebrating the release of “Conversance,” the first jazz album released by Pravda Records. DJ Pickled Beets opens at 7 p.m. May 24 at Space, 1245 Chicago Ave., Evanston. Tickets: $23.87-$31.59. Visit evanstonspace.com.
  • Warm Love Cool Dreams Music and Arts Festival features performances by Courtney Barnett, Toro y Moi, The Jesus and Mary Chain, Tortoise, Whitney, Pixel Grip, Nourished By Times, Smerz and many more. From May 23-24 at The Salt Shed, 1357 N. Elston Ave. Tickets: $75+. Visit saltshedchicago.com.
  • Forever Mine Music Festival showcases R&B and house artists who had an impact on the music scene in the early 2000s. Performers on three stages include Keyshia Cole, Kelly Rowland, Kaytranada, Juvenile and The 400 Degreez Band, Monica, Shaggy, Mario, JoJo, Bobby V and more. From noon-10 p.m. May 23-24 in Union Park, 1501 W. Randolph St. Tickets: $135+. Visit foreverminefest.com.

    Miss Grit - photo by Hoseon Sohn.jpg

    Miss Grit Miss Grit (aka Korean-American musician Margaret Sohn) performs May 21 at Empty Bottle, 1035 N. Western Ave.

    Hoseon Sohn

  • Miss Grit (aka Korean-American musician Margaret Sohn) tours behind their new album, “Under My Umbrella.” Brooklyn Vegan says Miss Grit is an artist with “a clear vision [who] knows how to make music that’s both off-kilter and widely appealing.” Also on the bill: Irish experimental rock band Just Mustard. At 9 p.m. May 21 at Empty Bottle, 1035 N. Western Ave. Tickets: $26.78. Visit emptybottle.com.

Museums

Excavator Pikachu - credit is The Pokémon Company group_Field Museum.jpg

Excavator Pikachu

The Pokémon Company group/Field Museum

  • Making its North American debut, “Pokémon Fossil Museum” is a one-of-a-kind experience that brings together the worlds of Pokémon and paleontology. Visitors can compare fossil Pokémon with real-world fossils, including Sue the T. rex. The exhibit features “Professors” from the Pokémon world, their helper Excavator Pikachu and Field Museum scientists. From May 22-April 11, 2027, at Field Museum, 1400 S. DuSable Lake Shore Dr. Admission: $21+ plus additional $13, $18 for Pokémon. Visit fieldmuseum.org.

Monumental Sculpture by Dr. Charles Smith  Courtesy of Intuit Art Museum6.jpg

“Monumental: Sculpture by Dr. Charles Smith” examines the artist’s expansive output of sculptures through the lens of “anti-monumentalism,” a contemporary art form designed to challenge, invert and reject the conventions of traditional monuments.

Courtesy of Intuit Art Museum

  • “Monumental: Sculpture by Dr. Charles Smith” examines the artist’s expansive output of sculptures through the lens of “anti-monumentalism,” a contemporary art form designed to challenge, invert and reject the conventions of traditional monuments. To April 25, 2027, at Intuit Art Museum, 756 N. Milwaukee Ave. Admission: $20, ages 24 and under free; from 5-7 p.m. on May 21 admission is free with curators on hand to discuss all the museum’s exhibits. Visit art.org.

Family fun

Wonder Woods Mini Golf - Credit The Morton Arboretum.jpg

Wonder Woods Mini Golf is a tree-themed course exploring how tree rings can tell the life story of a tree and how trees support the ecosystems of bugs and wildlife at the Morton Arboretum.

The Morton Arboretum

  • Wonder Woods Mini Golf is a tree-themed course exploring how tree rings can tell the life story of a tree and how trees support the ecosystems of bugs and wildlife. Begins May 22 at Morton Arboretum, 4100 Ill. Rt. 53, Lisle. Admission prices vary; Wonder Woods $4-$10. Visit mortonarb.org.
  • Young People’s Theatre stages “The Hula-Hoopin’ Queen,” Gloria Bond Clunie’s adaptation of Thelma Lynne Godin’s children’s book about a spunky Harlem girl and her friends as they take part in a Hula-Hoop competition. To May 31 at Greenhouse Theater, 2257 N. Lincoln Ave. Tickets: $26.50+. Visit greenhousetheater.org.

Dinos - Pterosaur - courtesy of Dino Don, Inc.JPG

The pterosaur is among the 35 life-size dinosaurs throughout the Brookfield Zoo grounds starting May 22.

Courtesy of Dino Don, Inc.

  • Dinos! features 35 life-size dinosaurs throughout the Brookfield Zoo grounds. Explore a massive rib-cage tunnel, climb on a giant fossil, dig for ancient discoveries and more. May 22-Oct. 25 at Brookfield Zoo, 8400 31st St., Brookfield. Admission: $23.95-$32.95, children 2 and under free. Visit brookfieldzoo.org.
  • Mutuall Design presents Fútbol for All 2026, a celebration of peace, love and the free spirit of fútbol. Included are futbol-themed activities including a jersey screen-printing station, a FIFA tournament, soccer trivia, creative crafts and more. From 5:30-8 p.m. May 21 at Design Museum of Chicago, 72 E. Randolph St. Admission is free. Visit designchicago.org/events.

Festival fun

  • Celebrate community and the coming of summer at the Belmont-Sheffield Music Fest, which features music on three stages, dozens of food vendors, artisans and local vendors. From 5-10 p.m. May 22 and 11 a.m.-10 p.m. May 23-24 on Sheffield Avenue from Belmont Avenue to Roscoe Street. Admission: $10 suggested donation. Visit chicagoevents.com.
  • Randolph Street Market Festival’s annual Garden Party Market is an indoor-outdoor treasure hunt featuring more than 200 antique and vintage vendors with fashion, vinyl, estate jewelry, decorative objects and more. From 10 a.m.-5 p.m. May 23-24 at 1341 W. Randolph St. Admission: $15. Visit randolphstreetmarket.com.
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