Alaina Kai Chester is an actor originally from Cincinnati, Ohio, and currently based in Brooklyn, New York. Alaina understudied the lead role of Sheila in The Trees at Playwrights Horizons, directed by Tina Satter and written by Agnes Borinsky. She was also in the original cast, and an understudy in the New York cast, of FLEX by Candrice Jones, which made its New York debut in 2023.

Alaina continues to create and evolve, blending song and story while bringing groundedness, passion, and a thoughtful approach to her artistry.

Lucille lortel awards (2024)

“FLEX”, nominated for Outstanding Ensemble.

Cast of "The Tress" at Playwrights Horizons

Full cast of “The Trees” at Playwrights Horizons (co-produced with Page73).

"44 Young Theatremakers Flex Their Muscles With 24 Hour Plays: Nationals"

“An off-shoot of the popular annual series in New York City, The 24 Hour Plays: Nationals—the program for artists 25 and under—has been cultivating the future of theatrical talent since 2013.” - Playbill.com /Ruthie Fierberg , 2019

Refuge: A solo short play

A demo from the full performance at Actors Theatre of Louisville. Explores the beautiful mystery behind Lauryn Hill's life after the Fugees split, and the release of her hit solo debut, The Miseducation of Lauryn Hill. Performed at Actors Theatre of Louisville. Directed by Kevin Craig West / Dramaturgy by Janelle Baker / Written by Alaina Kai Chester