The San Luis Obispo County Regional Airport began as one man's dream. Earl Thomson, along with his brothers-in-law, William "Chris" and David Hoover, talked county officials into leasing them the land. By April 1939, the airport opened with an 88-by-100 foot hangar and dirt runways.

In 1940, hard surface runways and lights were installed by the War Department. In 1940 and 1941, 183 private pilots and 20 advanced students were trained here through a federally sponsored Civilian Pilot Training Program for armed services fliers.

The federal government took over the airport through World War II, turning it back to the county in 1946. Additionally, Southwest Airways inaugurated a passenger and airline service that year.

In 1947, county supervisors contracted for another hangar, ramp, and eventually an administration building. The supervisors named Chris Hoover full-time airport manager in 1953.

In 1987, the San Luis Obispo County Regional Airport was dedicated as McChesney Field, in honor of Leroy E. McChesney for his leadership and dedication to aviation. Mr. McChesney resided in the county since 1920 and had been a pilot since 1949. He was a longtime member of the California Aviation Council, a member of the California Aeronautics Board, and other aviation organizations. Mr. McChesney was the Grand Marshal of the first Airport Day in 1984.

Airport facilities now include a terminal building, restaurant, hangars and numerous other airplane related businesses. In 1988, an air traffic control tower was opened by the Federal Aviation Administration.

Although Southwest Airways started airline service here in 1946, it only lasted until 1955. Southwest replaced it's DC-3's with Martin 404's, which were too large for the 4,000 foot runway, so they moved to Paso Robles. There was a long gap in air passenger service until Swift Aire Lines was started up in 1969. By the time that the control tower opened in 1988, Wings West, Skywest, WestAir, and later, American Eagle were in operation. Passenger service from San Luis Obispo was here to stay. Today, two regional airlines serve the community:  United Express (Skywest Airlines) and U.S. Airways (Mesa Airlines).