Fall always brings a focus on the big regional theaters, and this season delivers. Lookingglass is staging Gregg Ostrin’s “Kowalski,” starring Emmy nominee Johnny Galecki (“Roseanne,” “Big Bang Theory”). Steppenwolf’s scathing drama “Topdog/Underdog,” which won writer Suzan–Lori Parks a Pulitzer, puts Tony nominee Glenn Davis toe-to-toe with Namir Smallwood, who was recently on Broadway in Tracy Letts’ drama “Bug.”
But as the Broadway in Chicago remount of Kokandy’s hit musical “Jekyll & Hyde” illustrates (opening Sept. 8), the place to see the next big thing is on the city’s storefront stages. So I decided to focus my fall 2026 list in Off Loop, neighborhood theaters.
Here are 10 shows to see this season on Chicago’s smaller and midsize stages.
Blood of the Lamb (Chicago premiere)
Where: The Den Theatre, presented by Promethean Theatre Ensemble
When: Through Oct. 3
What storefront theater lacks in budget, it recoups through creativity. This two-hander, by playwright Arlene Hutton ( “Last Train to Nibroc”), is a thriller set two days from right now. A woman on a cross-country flight from California to New York is diverted and detained in Dallas. She wants on the next flight out, but being pregnant, in Texas, turns that into a political problem. The production, helmed by Chicago director Anna C. Bahow, splits the two roles between four actors in a cast that includes two-time Jeff nominee Meghann Tabor and Promethean ensemble member Heather Dennis. 1331 N. Milwaukee Ave.
How We Got On (world premiere)
Where: Definition Theatre
When: Sept. 11–27
Hyde Park’s Definition Theatre deserves attention. Operating across the street from the University of Chicago’s Court Theatre, Definition is known for staging new works by emerging playwrights, with ensemble member James Ijames winning the Pulitzer for his play “Fat Ham.” The world premiere “How We Got on,” directed by founding Artistic Director Tyrone Phillips, is written by theater vet Idris Goodwin, who uses music in the storytelling. This world premiere follows three suburban teens who discover hip-hop and have their lives forever changed. 1160 E. 55th St.
Detroit ‘67
Where: eta Creative Arts Foundation, presented by Pulse Theatre
When: Sept. 11–Nov. 1
Written by two-time Tony nominee (“Ain’t Too Proud” and “Skeleton Crew”) and MacArthur “Genius” Dominique Morisseau, “Detroit ‘67” is the first of the three-play cycle called The Detroit Project. Inspired by legendary playwright August Wilson’s Pittsburg Cycle, Morisseau, a Detroit native, penned the plays chronicling Black life in her hometown in three different eras. “Detroit ‘67” unfolds in a Detroit basement with the 1967 riots happening outside and the sounds of Motown blaring inside. Directed by Pulse founding artistic director Aaron Reese Boseman, this drama follows two siblings who have their lives interrupted by the entrance of a stranger who unearths secrets. 7558 S. South Chicago Ave.
Bonnie’s Last Flight (world premiere)
Where: Rivendell Theatre
When: Sept. 12–Oct. 17
Written by Eliza Bent, this production is technically a quirky workplace comedy, which we’re all pretty familiar with. Here’s the rub: this workplace is an airplane. Jan, played by Jeff Award winner Rebecca Spence (“Every Brilliant Thing”), is taking her last flight and everyone knows except her best friend, Greig, played by Paul Oakley Stovall (Tony Award for producing “A Strange Loop”). Director Devon de Mayo will have her hands full creating action in the contained tubular body of a plane. But she has excellent actors to work with as the cast also includes Jeff Award winner Jessica Ervin (Rivendell’s “Motherhouse”), LaKecia Harris (Manual Cinema’s “A Christmas Carol”) and Glenn Obrero, who had memorable roles in Rivendell’s “Pivot” and A Red Orchid’s “The Targeted.” 5779 N. Ridge Ave.
I’m Gonna Marry You Tobey Maguire (Chicago premiere)
Where: The Den Theatre, presented by Refracted Theatre Company
When: Sept. 18–Oct. 31
If the year is 2004 and an eighth grade girl is going to kidnap a celebrity, Spiderman is a likely candidate. This dark comedy, by playwright Samantha Hurley, premiered in New York in 2023 and now makes its Chicago premiere with Refracted Theatre Company. It’s the highly anticipated return of the company that became Chicago’s storefront darling after sweeping the 2024 Jeff Awards with “Tambo & Bones.” In “Tobey Maguire,” directed by Tyler Struble, eighth-grader Shelby Hinkley (Alex O’Shea) kidnaps her celebrity crush. That action fuels a production that explores the oft-problematic, para-social relationships of the social media age, through the lens of a Y2K teen. 1331 N. Milwaukee Ave.
Prayer Circle (world premiere)
Where: Redtwist Theatre
When: Sept. 20–Nov. 8
This world premiere by Jeff Award-winning playwright Erik Gernand (“The Totality of All Things”) dives into a prayer circle. The circle’s participants make a chilling discovery that poses a simple question: What if your prayers had the power to kill? From there, the dark comedy, directed by Redtwist Executive Artistic Director Dusty Brown, explores how far a small congregation will go to save the country. The cast includes Jeff Award winners Jacqueline Grandt (Queen Elizabeth in Theo Ubique’s “Diana”) and Andi Muriel (Rivendell’s “Motherhouse”). 1044 W. Bryn Mawr Ave.
Any Rebellion of Will (Chicago premiere)
Where: Trapdoor Theatre, in partnership with Independent Projects Initiative and Grey Area Productions
When: Oct. 8–Nov. 1
Award winning Chicago playwright S.L. Daniels has penned a story that wraps a tale of incel uprising in fantasy with vaudeville stylings and magic. Will, played by Humboldt Park native Lenin Izquierdo (“The Brief Wondrous Life of Oscar Wao at the Goodman”), is kicked out of his parents’ home. Inspired by an article about the Japanese Hikikomori – a phenomenon where adult men live at home and are fully dependent on their parents — Will returns home with a mystical street performer and brings chaos to his parents. The production is directed by Spencer Huffman, who made a name for himself producing and directing shows in a titanium factory. The cast also includes Jeff Award winner Larry Grimm, playing opposite Jeff Award winner Shawna Franks (“Right Now” at Facility Theatre). 1655 W. Cortland St.
A Strange Loop (Chicago Premiere)
Where: Raven Theatre, in partnership with About Face Theatre
When: Oct. 8–Nov. 8
This production is exciting for a few reasons: Raven recently put a toe into the waters of staging musicals with “Octet.” That show was a huge success and was transferred to the Goodman for an extension. This show will be Raven’s first time staging a full-on musical (and WBEZ will be there to host Theater Club on Oct. 18). Directed by the Chicago based multi-Jeff Award-winner Mikael Burke (Remy Bumpo’s “Blues for an Alabama Sky” and Refracted Theatre’s “Tambo & Bones”), this Chicago premiere is one of the most anticipated shows on this list. The production, written by Michael R. Jackson, won the Pulitzer Prize for Drama in 2020 and the Tony for Best New Musical in 2022. The story follows Usher, a Black queer playwright (Eddie Weaver) working as an usher on Broadway. He’s struggling to write a play — about a Black queer usher on Broadway who is struggling to write a play. It’s heady, time-loopy and set to music. 6157 N. Clark St.
Radical Futures (world premiere)
Where: The Factory Theater
When: Oct. 16–Nov. 21
Shows like this are what make Chicago storefront special. (I recently visited the Factory Theater for Strawdog’s “Advance Man” and it was so weird… I loved it.) These companies take swings and stage shows that may be weird, or wonky or in this case, a risky new sci-fi production, that may or may not work — but will definitely be fun. “Radical Futures,” written by B.Z. Florida, who writes sci-fi plays and comics, is set in a place Chicagoans have a soft spot for: a dive bar. That’s a good start. From that familiar place things take a strange turn. Directed by Kayla Menz, this production asks: Can we change our futures? Are the friends we currently hold close going to be there in the long run? Does it matter? The journey sounds interesting. 1623 W. Howard St.
A Clockwork Orange: A Play with Music
Where: The Chopin Theatre, presented by Kokandy Productions
When: Nov. 5–Jan. 10
Kokandy has a reputation for taking big Broadway musicals and cleverly staging them in a Wicker Park basement theater. This musical version of Stanley Kubrick’s cult classic film was adapted by Anthony Burgess, who wrote the original novel. Burgess crafted the play with the intention of it being staged with limited sets and props. Kokandy hasn’t announced casting, but artistic director Derek Van Barham will direct and Breon Arzell will choreograph, which is a promising place to start. The material itself is rather graphic, and the idea of setting it to Beethoven-inspired music is… an intriguing cap for the fall season. 1543 W. Division St.