Chester Eagle was born at Bendigo and educated at Melbourne Grammar and the University of Melbourne. He worked as a teacher and administrator in Victorian colleges of Technical and Further Education until his retirement in 1988.
Eagle is most-admired for his autobiographies Mapping the Paddocks (1984) which won the Age Book of the Year for non-fiction, and Play Together, Dark Blue Twenty (1986). The former recounts his rural boyhood and a search for meaning, ending with the bombing of Hiroshima. The latter describes his experiences at Melbourne Grammar from 1946 to 1951. These autobiographies add to his earlier memoir Hail and Farewell! (1971), an account of his twelve years in Gippsland.
Eagle has also published several collections of short stories and a number of novels. In the 1970s he published Who Could Love the Nightingale (1973) and Four Faces, Wobbly Mirror (1976). Since then, his fiction has been published regularly. In the 1990s he completed two novels, and a collection of stories. He also edited Didgeridoo: Some Histories (1999).