Chesnutt was the daughter of novelist Charles Chesnutt. She earned her B.A. from Smith College (1902) and her M.A. in Latin from Columbia University (1925). She taught Latin at Central High School in Cleveland. One of her pupils, Langston Hughes, found her inspiring. In 1932 she co-authored The Road to Latin (1932), a textbook that was published several times. She belonged to the American Philological Association (1920-1934).