America looked skyward when Charles Lindbergh made the first transatlantic flight in 1926. Cortland County was no exception.

The Cortland Flying Club began with a vision in the late 1920's. Property was leased around 1927 from three farmers on the sparsely populated Groton Road. The grassy fields were separated by stone walls, portions of which were removed to create a runway.

The Cortland Airport was organized in 1929 and a hangar built. A year later, the Works Progress Administration graded the grass field to improve landing capability. The city agreed on a barbed-wire fence to prevent night trespassers and a huge airport dedication ceremony was planned.

From 1933 through 1934, Edwin Link, developer of the revolutionary Link Trainer, the first of which was built at the Cortland Airport, was airport manager. In keeping with his motto "Management and Progressiveness", the airport became the only fully equipped, government licensed repair shop between Washington, D.C. and Ottawa.

In 1940, the Cortland Flying Club formally sold the property to the city of Cortland for $16,000. By the early 1960's, the city maintained it could no longer operate the 68 1/2 acre airport, and began negotiations with the county. Housing had begun to encroach upon the airport, and to ensure the safety of the residents, improvements such as lighted, paved runways and clear zones to protect approaches were put into place. In 1965, after much discussion, the city offered the county clear title to the airport property for $35,000.

In 1966, a new radio system was put into place and 16 T-hangers built, rented on a monthly or yearly basis. Robert Crocker became county airport manager in 1968 and began Air Cortland, Inc., the first charter air service located in the county.

The airport was formally named "Levi R. Chase Field" after General Levi R. Chase in 1970, a Cortland native who had flown in over 500 missions through three wars.