Chester E. Dempsey (July 20, 1896 – October 4, 1969) was an American farmer and politician. Born in the town of Merton, Wisconsin, Dempsey owned and operated a dairy farm. He served on the Waukesha County, Wisconsin Board of Supervisors and in town government. He served in the Wisconsin State Senate, as a Democrat, 1935-1939 and, as a Republican, 1947 until his death on October 4, 1969.