[1] She began her career as a child actor in the films A Little Princess (1995) and Harriet the Spy (1996), before her breakthrough role in Steven Spielberg's The Lost World: Jurassic Park (1997).

Chester was born on July 2, 1984, at Brooklyn, New York City,[2] to Guyanese parents who immigrated to the United States.

In her early childhood, she relocated with her mother to Los Angeles, California, where she began auditioning for and appearing in commercials.

[1] In 1996, she appeared opposite Michelle Trachtenberg as Janie in the Nickelodeon film Harriet the Spy, which was a moderate box office success.

[3] The following year, she was cast in a lead role as Kelly in Steven Spielberg's The Lost World: Jurassic Park (1997),[4] playing the daughter of Ian Malcolm (Jeff Goldblum).