Chester Castle Bolton (September 5, 1882 – October 29, 1939) was a U.S. representative from Ohio. He served four consecutive terms from 1929 to 1937. He was elected to a fifth term in 1938, but he died before completing the term.

He was the husband of Frances P. Bolton, who succeeded him in Congress, and the father of Oliver P. Bolton. Frances and Oliver Bolton would themselves become the first mother and son to serve simultaneously in Congress.

Born in Cleveland, Ohio, Bolton attended the city's public schools. He graduated from the University School in Cleveland in 1901, and from Harvard University in 1905, where he was a member of the Delphic Club.

Chester Castle Bolton and Frances Payne Bingham Bolton were married in 1907. They had 4 children, Charles B. Bolton, Oliver Payne, Kenyon C., and Elizabeth Bolton.

Bolton was a business industrialist in the steel industry in Cleveland from 1905 to 1917. He served as member of the Ohio National Guard from 1905 to 1915.

Bolton was commissioned as a captain in the Reserve Corps, and then was ordered into active service in March 1917, in World War I. He was detailed first to the War Industries Board, and then served as aide to the Assistant Secretary of War. He was transferred to the General Staff in 1917. He was promoted to the rank of lieutenant colonel and detailed to the One Hundred and First Division as Assistant Chief of Staff, and was discharged in December 1918.

He returned to Cleveland, Ohio, and served as a director of several large business corporations, and also engaged in raising and breeding a renowned Guernsey cattle herd at Franchester Farms, on the Bolton's 65 acre family estate 'Franchester Place' in Lyndhurst, Ohio.

He served as member of the Lyndhurst Village Council from 1918 to 1921.