Lookingglass Theatre Company Sets World Premieres and More for 2025–2026 Season

Lookingglass Theatre Company has announced its 2025–2026 season, featuring two world premieres by Company Members Matthew C. Yee and Kevin Douglas, the return of the acclaimed Lookingglass Young Ensemble, and the continuation of the powerful annual ritual Sunset 1919. The season will take place in the Joan and Paul Theatre, 163 E. Pearson St. at Michigan Ave.

The new season kicks off with TimeLine Theatre Company’s production of Hundreds and Hundreds of Stars (Oct–Nov 2025), a world premiere hosted by Lookingglass and directed by Kimberly Senior, before Lookingglass launches its in-house programming in December.

“This season is a celebration of our ensemble’s originality, humor, and heart,” said Artistic Director Kasey Foster. “Matthew C. Yee and Kevin Douglas bring two wildly different but equally brilliant new plays to the stage, both full of poignancy and unexpected laughs. And with Heidi Stillman leading our Young Ensemble and Sunset 1919 returning next summer, we continue to honor our commitment to emerging artists, community storytelling, and theatrical innovation.”

2025–2026 Season at a Glance:

Lookingglass Young Ensemble Production

December 2025
Directed by Heidi Stillman
Joan and Paul Theatre at Water Tower Water Works

Lookingglass kicks off its season with a new work by the acclaimed Lookingglass Young Ensemble, now in its 27th year. This devised piece, developed and performed by Chicago-area youth ages 13–18, blends language, music, movement, and visual storytelling in signature Lookingglass style.

World Premiere: WHITE ROOSTER

March–April 2026
Written and Directed by Matthew C. Yee
Joan and Paul Theatre

A haunting, darkly comic tale of grief and family, White Rooster follows Min as she navigates loss, restless spirits, and old family superstitions. Her fiancé won’t stay dead, her sister won’t stay buried, and a rooster demands to be heard. This world premiere fuses spooky folklore with biting humor in a singular theatrical experience.

World Premiere: UNTITLED VAMPIRE PLAY

June–July 2026
Written by Kevin Douglas
Directed by Devon DeMayo
Joan and Paul Theatre

Vampires, codependency, and comedic chaos collide in this new play from longtime ensemble member Kevin Douglas. When Val—a vampire—starts a relationship with a mortal, complications arise involving immortal exes, family drama, and a serial killer on the loose in Chicago. This horror-infused comedy is as heartfelt as it is hilarious.

Lookingglass Outdoors Presents: SUNSET 1919

Monday, July 27, 2026 at 7 p.m.
The Eugene Williams Memorial, 125 Fort Dearborn Dr.

Now a vital annual tradition, Sunset 1919 commemorates the murder of Eugene Williams and the 1919 Chicago race riots with an artistic ritual of music, movement, and reflection. Co-curated by J. Nicole Brooks and Kareem Bandealy, this free community performance honors Black lives lost and carries forward the legacy of resistance and remembrance.

Featuring: Pugs Atomz, Rae Chardonnay, Aaliyah Christina, Glenn Felix Willoughby, olula negre, Julian Otis, and Fawn E. Pochel.

Also at Lookingglass: TimeLine Theatre’s WORLD PREMIERE

Hundreds and Hundreds of Stars

October–November 2025
Written by Sandra Delgado, Directed by Kimberly Senior
Presented by TimeLine Theatre Company
Tickets at TimeLineTheatre.com

This moving, magical realist drama follows Clara, a single mother whose path to U.S. citizenship unearths long-buried personal history and raises questions about identity, belonging, and the cost of the American dream.

Chicago Awards - Live Stats

Best Musical - Top 3

1. RENT (Highland Park Players)

7.1% of votes

2. HAIRSPRAY (Uptown Music Theater of Highland Park)

7% of votes

3. DREAMGIRLS (The Drama Group)

6.4% of votes

Vote Now!