Chesney later played professional football with the Chicago Bears in 1939 and 1940.
He entered the United States Air Force in June 1941 as a private and was discharged as a major in 1946 with service in the Pacific and European Theaters. He served as assistant chief of special service, Veterans Administration, Hines, Illinois, in 1946 and 1947.
After the war, he took graduate work at Northwestern University Graduate Commerce School in 1947. He became an Executive with Montgomery Ward & Co., in 1948 and 1949. He later served as vice-president and director of Avondale Savings & Loan Association.
Political career
Chesney was elected as a Democrat to the Eighty-first Congress (January 3, 1949 – January 3, 1951). He was an unsuccessful candidate for reelection in 1950 to the Eighty-second Congress, though served as delegate to the 1968 Democratic National Convention.