October on Chicago Stages: The Shows That Matter
October is when Chicago theater stops warming up. Resident companies are in full stride, the Loop has a short list of musicals that will sell, and Lyric opens a new season. Here are the shows worth your money this month — starting with the five that define it.
The five that define the month
- Topdog/Underdog
Steppenwolf Theatre, Downstairs
September 29–November 1
Suzan-Lori Parks’s Pulitzer Prize–winning play about brothers Booth and Lincoln, directed by Kenny Leon. This is the prestige play of the fall, and it runs the entire month.
Tickets: Steppenwolf
- Play On!
Chicago Shakespeare Theater, The Yard at Navy Pier
Through October 18
Shakespeare’s Twelfth Night reset to Duke Ellington’s songbook — Cotton Club swing with a real score stack. Built to travel, and the best musical still playing when the month begins. See it before it closes in the first two weeks of October.
Tickets: Chicago Shakespeare
- Jekyll & Hyde
Broadway Playhouse at Water Tower Place
Through October 25
Kokandy’s revival of the gothic pop-rock musical at Broadway Playhouse. The month’s longest-running commercial sit-down — Halloween-adjacent without tipping into novelty.
Tickets: Broadway Playhouse
- Operation Mincemeat: A New Musical
CIBC Theatre
September 29–October 11
2025 Tony winner and Olivier winner: a WWII con job with a dead body, a bogus letter, and Ian Fleming in the wings. Short Loop run — done by Columbus Day. Catch it early.
Tickets: CIBC Theatre
- Don Giovanni
Lyric Opera of Chicago
October 10–November 1
Directed by Robert Falls. Christian Van Horn in the title role (Kyle Ketelsen takes the final two performances). Lyric’s 2026/27 opener and the first of the Mozart/Da Ponte trilogy. The Oct. 18 matinee is billed as Lyric’s first live, ASL-interpreted foreign-language opera.
Tickets: Lyric
Also on the October board
Omar — Lyric Opera, Oct. 23, 25, 28 only. Company premiere of Pulitzer Prize winner by Rhiannon Giddens / Michael Abels. Three acts.
Waitress — Nederlander Theatre, Oct. 13–18. Sara Bareilles’s 10th-anniversary sit-down. Short, sweet, easy to catch.
The Book of Mormon October 23 – November 1. The tour that continues to sell.
The Attic: Things I’ve Seen While Lying On My Back — Goodman Theater, through Oct. 4. The 7 Fingers circus-theater. One show to go for the month. If you haven’t seen it, go this week.
Come From Away — Marriott Theater, through Oct. 18. In the round. The recommendation for clean suburbia remains.
Dead Girl’s Quinceañera — Goodman Owen Theater, through October. Presented with Chicago Latino Theater Alliance. Dark comedy.
Witch — Idle Muse at The Edge Off Broadway, through Oct. 10. Jen Silverman’s Halloween-season storefront play — without the camp.
The Winter’s Tale runs October 13 – November 26 in the Courtyard at Chicago Shakespeare.
Not the theater, but like October
World Music Festival Chicago — Sept. 25–Oct. 4, 2026 (citywide, including Chicago Cultural Center). Free performances from around the world, including the all-night Ragamala Indian classical music event in Preston Bradley Hall. Annual late Sept–early Oct; no tickets, first-come seating.
Chicago International Film Festival — Oct. 14–25, 2026 (Music Box, Siskel, AMC NewCity, Logan Center, and more). North America’s longest-running competitive international film festival. Tickets on sale now.