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Chickasha was founded by Hobart Johnstone Whitley, a land developer, banker, farmer and Rock Island Railroad executive. The founding took place in 1892 when the Chicago, Rock Island and Pacific Railway (Rock Island) built a track through Indian Territory. A post office was established in June 1892. One of the earliest industrial plants to come to Chickasha was the Chickasha Cotton Oil Company, which was established in 1899. The town incorporated in 1902.
In 1908, the Oklahoma Industrial Institute and College for Girls was established in Chickasha. A local rancher named J. B. Sparks donated land for the school in memory of his daughter, Nellie. The girl was a Chickasaw descendent, and the land had been part of her allotment. The Nellie Sparks Dormitory commemorated her. The school was renamed as the Oklahoma College for Women in 1916. It became coeducational in 1965, and was renamed the Oklahoma College of Liberal Arts. It was renamed again in 1975 as the University of Science and Arts of Oklahoma.
The Wilson and Bonfis Flying School opened in October 1941 to train cadets of the U.S. Army Air Force. Over eight thousand cadets completed training there during World War II. After the war, the facility became the Chickasha Municipal Airport.
Also during the war, the army built and used Borden General Hospital. This site now contains Grady Memorial Hospital, Five Oaks Medical Group, Southern Plains Medical Center and Borden Park.
A prisoner of war camp established in 1944 is now the site of the Grady County Fairgrounds.