Chester Ashley (June 1, 1790 – April 29, 1848) was an American politician who represented Arkansas in the United States Senate from 1844 until his death.

Ashley was born in Amherst, Massachusetts in 1790; while a child he moved with his parents to Hudson, New York.

For some twenty years Ashley's practice was the largest in the state, and he became a wealthy man.

He also owned slaves (including the father of Little Rock teacher Charlotte Andrews Stephens), speculated in land, and was the owner and operator of plantations in the southeastern portion of the state.

[3] One of Ashley's descendants is Sterling R. Cockrill, the Democratic Speaker of the Arkansas House of Representatives from 1968 to 1969 and the unsuccessful Republican nominee for lieutenant governor in 1970.