- Director Tyrone Phillips reimagines Shakespeare’s clever comedy “Twelfth Night,” a tale — now set in the Caribbean — about the power of romance as Viola (Jaeda LaVonne) finds herself in the middle of a love triangle of mistaken identity. From Oct. 25-Nov. 26 at Chicago Shakespeare Theater, 800 E. Grand. Tickets: $38+. Visit chicagoshakes.com.
- Music Theater Works presents “Brigadoon,” Lerner and Lowe’s classic musical set in the Scottish Highlands, where two American tourists (Conor Jordan, Zachary Linnert) get lost and stumble on a mythical village that appears for a single day every 100 years. Sasha Gerritson directs. From Oct. 19-Nov 12 at North Shore Center for the Performing Arts, 9501 Skokie Blvd., Skokie. Tickets: $39-$106. Visit musictheaterworks.com.
- “The Night of the Hunter” is Shawna Tucker’s adaptation of novelist Davis Grubb’s noir thriller about a killer and his quest for hidden money. Brian Pastor directs the world premiere. From Oct. 20-Dec. 3 at City Lit Theatre, 1020 W. Bryn Mawr. Tickets: $34. Visit citylit.org.
- Yosimar Reyes’ “Prieto” is an autobiographical one-man show about his experience growing up queer and undocumented in East San Jose with his overprotective grandmother. Co-directed by Kat Evasco and Sean San Jose. From Oct. 20-22 at Chicago Shakespeare Theater, 800 E. Grand. Tickets: $35+. Visit chicagoshakes.com.
- “Nunsense” is Dan Goggin’s popular musical about nuns organizing a fundraiser to bury their deceased sisters accidentally poisoned by the convent cook. From Oct. 20-Nov. 12 at Saint Sebastian Players at St. Bonaventure, 1625 W. Diversey. Tickets: $35. Visit saintsebastianplayers.org.
- BrightSide Theatre stages “A Little Night Music,” Stephen Sondheim and Hugh Wheeler’s musical about an actress’ chance encounter with an old flame that leads to romantic misadventures. From Oct. 20-Nov. 5. North Central College, Meiley-Swallow Hall, 31 S. Ellsworth, Naperville. Tickets: $32-$37. Visit brightsidetheatre.com.
- Steven Sapp and Mildred Ruiz-Sapp present a reading of “In the Beginning There Was House,” their new play inspired by the life and work of Chicago house music legend Frankie Knuckles. Chay Yew directs. From Oct. 20-21 at Northwestern University’s Wirtz Center, 710 N. DuSable Lake Shore Dr. Tickets: $8-$15. Visit wirtz-northwestern.edu/chicago.
- Zephyr Dance presents a collaborative choreography project that combines Merce Cunningham’s “Suite for Five” and new choreography that springs from that work for the new piece “S45,” created by a diverse group of choreographers including Paige Cunningham-Caldarella, a former Cunningham company dancer. From Oct. 19-22 at SITE/less, 1250 W. Augusta. Tickets: $25. Visit zephyrdance.com.
- Molly Shanahan/Mad Shak debuts a new evening-length work, “Ex/Body: strike, vibrate, shatter,” which explores the impact and potential of trauma as a source of embodied wisdom. Composer Zachery Meier’s score was created in the studio during the making of the work. From Oct. 21-22 at Studio5 Performing Arts Center, 1938 Dempster, Evanston. Tickets: $35. Visit studio5.dance/calendar.
- Brandy Clark tours behind her newest self-titled release, produced by Brandi Carlile, which has been called an “American masterpiece.” One of her generation’s most respected songwriters and musicians, Clark has created a raw and intimate album that showcases her versatility. SistaStrings opens at 8 p.m. Oct. 19 at Thalia Hall, 1807 S. Allport. Tickets: $25. Visit thaliahallchicago.com.
- Chicago Symphony Orchestra performs a program featuring George Gershwin’s Piano Concerto in F with pianist Conrad Tao, Leonard Bernstein’s Symphonic Dances from “West Side Story,” plus Barber’s “The School for Scandal” Overture and Revueltas’ “Sensemaya.” James Gaffigan conducts. At 7:30 p.m. Oct. 19-21, 24 at Symphony Center, 220 S. Michigan. Tickets: $35-$250. Visit cso.org.
- K-pop powerhouse Enhypen formed during the pandemic when touring was at a standstill, but nevertheless the seven members were able to find success and legions of fans. They close out their U.S. tour with a performance at 7:30 p.m. Oct. 22 at United Center, 1901 W. Madison. Tickets: $107+. Visit ticketmaster.com.
- After 13 years, Soul Summit, the much loved celebration of Chicago soul and funk, ends with a final party at 9 p.m. Oct. 21 at Empty Bottle, 1035 N. Western. Join DJs Duke Grip, Sloppy White and Mo Manley and dance the night away to some great music. Admission is free until 10 p.m., $5 after. Visit emptybottle.com.
- “When You Wish Upon A Star: A Jazz Tribute to 100 Years of Disney” features the newly created house band of the National Jazz Museum under the direction of Sean Mason performing versions of Disney classics recorded by Louis Armstrong, Miles Davis, Dianne Reeves and more. Featured vocalists are Kim Nalley and Sasha Dobson. At 7:30 p.m. Oct. 21 at McAninch Arts Center, 425 Fawell Blvd., Glen Ellyn. Tickets: $50-$65. Visit atthemac.org.
- Classical music meets hip-hop in the music of Black Violin, a duo featuring Will Baptiste on viola and Kev Marcus on violin. At 7 p.m. Oct. 22 at Genesee Theatre, 203 N. Genesee, Waukegan. Tickets: $25-$55. Visit ticketmaster.com.
- Singer-songwriter Victoria Monét has penned songs for the likes of Ariana Grande, Blackpink and Selena Gomez. Now she’s touring behind her debut album “Jaguar II.” At 7 p.m. Oct. 22-23 at House of Blues, 329 N Dearborn. $200+. Visit houseofblues.com/chicago.
- Celebrate the Great Filipino Songbook with SamaSama Project, a Chicago-based folk fusion band performing a modern take on iconic love songs. At 4 and 7 p.m. Oct. 22 at Davenport’s, 1383 N. Milwaukee. Tickets: $15. Visit davenportspianobar.com.
- Rapper, singer and songwriter Lil Uzi Vert (aka Symere Woods) performs at 6:30 p.m. Oct. 23 at Byline Bank Aragon Ballroom, 1106 W. Lawrence. Tickets: $114+. Visit livenation.com.
- The Canadian electro-funk duo Chromeo performs at 8 p.m. Oct. 22 at The Salt Shed, 1357 N. Elston. Tickets: $35-$55. Visit saltshedchicago.com.
- “I’ll Have What She’s Having: The Jewish Deli” explores how Jewish immigrants created a uniquely American restaurant that also served as a lifeline for Holocaust survivors and refugees. The immersive exhibit looks at the history of the deli through neon signs, menus, advertisements, uniforms, photographs, film and television. From Oct. 22-April 14 at Illinois Holocaust Museum, 9603 Woods, Skokie. Admission: $6-$18, children under 5 free. Visit ilholocaustmuseum.org.
- Photographer Steve McCurry is best known for his image of a young Afghan refugee, Sharbat Gula, which ran on the cover of National Geographic. It is just one of many striking images in “Icons,” a new retrospective exhibit of his work featuring more than 80 large-format photographs. The images are from four decades of McCurry’s travels around the world. From Oct. 20-Nov. 26 at Loyola University Museum of Art, 820 N. Michigan. Admission: $25. Visit feverup.com/m/140002.
- Arts in the Dark Halloween Parade brings together cultural organizations and artists from across the city for a free one-of-a-kind event featuring unique floats, spectacle puppets and performances. From 6-8 p.m. Oct. 21 on State from Lake to Van Buren. A candy giveaway begins at 5 p.m. Visit artsinthedark.com.
- Writers Theatre presents Filament Theatre’s “FORTS! Build Your Own Adventure,” an immersive playroom for families filled with couches, cardboard boxes, sheets, clotheslines and more where they can create a fort of their own design. At 10:30 a.m. and 1 p.m. Saturday and 11 a.m. and 1 p.m. Sunday from Oct. 19-Nov. 26 at Writers Theatre, 325 Tudor, Glencoe. Tickets: $20 (one adult can bring up to three children; children cannot attend alone). Visit writerstheatre.org.
- Celebrate autumn at Lincoln Park Zoo’s Fall Fest, an event featuring free music, pumpkin carvers and a pumpkin patch plus ticketed attractions including a slide, harvest maze, inflatable attractions and more. From 10 a.m.-5 p.m. Friday-Saturday through Oct. 29 at Lincoln Park Zoo, 2001 N. Clark. Visit lpzoo.org.
- Disney Junior Live on Tour: Costume Palooza features Disney Junior characters and Marvel Super Heroes in a concert-style show. At 4 p.m. Oct. 22 at Auditorium Theatre, 50 E. Ida B. Wells. Tickets: $29+. Visit auditoriumtheatre.org.
- 13th Floor Haunted House returns with its always terrifying lineup of ghouls and haunts that are not for the weak of heart. This year you can take a walk through the post-apocalyptic world of The Deadlands and visit the inhabitants of a small village who are displaying very odd behavior in Depths of Darkness. Open Wednesday-Sunday through Nov. 5 at 5050 River Rd., Schiller Park. Tickets: $30+. Visit 13thfloorchicago.com.
- Haunted Soiree: A Macabre Cocktail Party is an immersive experience held inside the former Eleanor Robinson Countiss House (now the International Museum of Surgical Science, 1524 N. DuSable Lake Shore Dr.), a mansion rumored to be haunted. Enjoy mini-cocktail tastings curated for the evening and uncover the evening’s ghost story, “The Vega Haunting,” by speaking with ghosts who are dying to talk about it. To Oct. 31. Admission: $69-$95. Visit hauntedsoiree.com/chicago.
- Redline VR’s Halloween offering is “Time Warp: A Rocky Horror Immersive Pop-up,” which transforms the space into the classic movie with Dr. Frank-N-Furter and his pals. Plus themed cocktails, photo ops, drag queen appearances and more. To Oct. 31 at Redline VR, 4702 N. Ravenswood. Free, upgrades begin at $20+. For more information on a wide range of programming, visit redlinevr.com.