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. (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. 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 (see our 2016 review).
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.
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.