Monday Night PlayGround at Looking Glass Thatre

Join us for new first-person solo pieces inspired by historical figures who contributed to the making of America over the past 250 years: those who helped dream it, build it, and/or lead it. Discover previously untold stories that deserve to be shared.

Each month, from November through April, PlayGround-Chicago announces a topic and invites Chicago’s best new dramatists to write and submit original ten-page plays. The best six of these plays are presented as staged readings via Vimeo live stream on the 1st Monday of the month, featuring some of Chicago’s best directors and actors. Tickets for online viewing are admission-free and must be reserved in advance. While the events are free, PlayGround-Chicago is grateful for donations made at the time of ticket reservation in support of our programs. NEW: Purchase a tax-deductible Monday Night PlayGround Membership ($50) and guarantee simulcast and extended on-demand access to all Chicago performances ($10 per event or just $1.66 per play).

2026-27 Monday Night PlayGround-Chicago Season: November 2, 2026 at The Den December 14, 2026 at Theater Wit February 1, 2027 at Chicago Dramatists March 15, 2027 at Chicago Theater Wit April 19, 2027 Best of PlayGround Chicago ’27 at Theater Wit