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 17–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
Closed Oct. 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.
Tickets: Chicago Shakespeare
- Jekyll & Hyde
Broadway Playhouse at Water Tower Place
Extended through November 8
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
Closed Oct. 11 (ran 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. It was a short Loop run.
Tickets: CIBC Theatre
- Don Giovanni
Lyric Opera of Chicago
October 10–November 1
Directed by Robert Falls. (For comparison, see our 2014 review of an earlier Lyric Don Giovanni.) 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. About 2 hours 40 minutes with one intermission.
Waitress — Nederlander Theatre, closed Oct. 18 (ran Oct. 13–18). Sara Bareilles’s 10th-anniversary sit-down.
The Book of Mormon — Cadillac Palace Theatre, Oct. 23–Nov. 1. The tour that continues to sell (see our 2016 review).
The Attic: Things I’ve Seen While Lying On My Back — Goodman Theatre, closed Oct. 4. The 7 Fingers circus-theater.
Come From Away — Marriott Theatre, extended through Oct. 25. In the round. The recommendation for clean suburbia remains.
Dead Girl’s Quinceañera — Goodman Owen Theater, extended through Nov. 8. Presented with Chicago Latino Theater Alliance. Dark comedy.
Witch — Idle Muse at The Edge Off Broadway, closed Oct. 10. Jen Silverman’s Halloween-season storefront play — without the camp.
The Winter’s Tale runs October 13–December 12 in the Courtyard at Chicago Shakespeare, in repertory with A Midsummer Night’s Dream from Nov. 11.
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.
Planning ahead? Holiday tickets are already moving: see our Chicago holiday shows guide and where to see The Nutcracker. To pair a matinee with a gallery visit, check our free museum days guide.