His first novel was You Remind Me of Me (2004). His short-story collections Fitting Ends (1996) and Among the Missing (2001) were both well-received; the latter was a finalist for a National Book Award and was also named one of the year's ten best books by the American Library Association and as a notable book of the year by The New York Times.
Chaon's short stories have won the Pushcart Prize and the O. Henry Award and have been included in the Best American Short Stories of 1996 and 2003. He was awarded the 2006 Academy Award in Literature from The American Academy of Arts and Letters.
His new novel, Await Your Reply, was published in August 2009 and was called one of the 10 best books of 2009 by Publishers Weekly.
Chaon was adopted and grew up in Sidney, Nebraska. He received his MFA from Syracuse. He was married to the late writer Sheila Schwartz and has two teenage sons. He presently lives in Cleveland Heights, Ohio and teaches creative writing at Oberlin College.