[5] The city is named for and strongly connected to Native American heritage, as "Chickasha" (Chikashsha) is the Choctaw word for Chickasaw.

Chickasha was founded by Hobart Johnstone Whitley, a land developer, banker, farmer and Rock Island Railroad executive.

[9] The Wilson and Bonfis Flying School opened in October 1941 to train cadets of the U.S. Army Air Force.

[9] Chickasha is located west of the center of Grady County and is 42 miles (68 km) southwest of Oklahoma City,[9] which is accessible via Interstate 44 (the H. E. Bailey Turnpike).

I-44 passes through the southeast side of the city, with access from Exits 80 and 83, and leads southwest 47 miles (76 km) to Lawton.

As of the United States Census Bureau, there were 16,231 people, 6,222 households, and 3,773 families residing in the city.

[16] In terms of educational attainment, 88.9% of residents 25 and older had at least a high school diploma, and 19.4% had a bachelor's degree or higher.

The majority of employed residents worked in private companies (72.39%), followed by government workers (15.58%), and self-employed individuals (8.23%).

[16] Agriculture, particularly wheat production, and cattle raising have been important to the city's economy since its earliest days.

[9] The city's annual Festival of Light takes place at the 43-acre (170,000 m2) Shannon Springs Park and opens nightly from around Thanksgiving to the end of December.

[23] The Scholastic Meet attracts around 1000 students annually from over 50 Oklahoma counties who compete in academic disciplines such as math, science, music, history, and other subjects.

[20] The Muscle Car Ranch located on the south edge of Chickasha hosts an annual swap meet and concert, which is held in August.

The Ranch, located on 70 acres (280,000 m2) of a 1900s dairy farm, features hundreds of nostalgic advertisements and memorabilia representing the last 75 years of American history.

[26] The concert has featured rock and roll groups such as The Byrds, The Grass Roots, Paul Revere & the Raiders, Jefferson Airplane, The Lovin' Spoonful, Firefall, John Conlee, Dr. Hook and Bad Company.

[30][31] It offers recreation such as swimming, boating, and water sports, as well as hiking, camping, and playground usage.

[32] Shannon Springs Park has a splash pad and pool, free fishing for those under 16 or over 65, playground equipment, an outdoor amphitheater, pavilions and more.

[32] The Chickasha Sports Complex hosts regional baseball, softball and soccer tournaments, as well as facilitating local games and practice sessions.

[33] Chickasha is the current location of a historic schoolhouse that served black children in Grady County.

[35] A branch of Canadian Valley Technology Center provides vocational and community education in Chickasha.