The airport was without a commercial airline from February 1933 through September 1940. At that time Eastern Airlines brought four commercial flights a day to Evansville Municipal Airport. This service to the area pointed out the need for the expansion of the airport's services. Mayor Dress and the Airport Board realized the benefits Evansville could receive from an enlarged airport, so a plan for expansion was developed.

In 1942, war leases at Evansville Municipal Airport began with Republic Aviation in May and the U.S. Government in August. During World War II, the airport was an operations base for ferrying aircraft detachments. In September, 1942, Republic Aviation completed the first Thunderbolt (P-47) aircraft. Some 6,075 Thunderbolt aircraft were manufactured in Evansville by Republic and delivered throughout the country and to overseas battlefront.

Because of imminent Army takeover in 1943, the Airport Board purchased 148 acres of land on Slaughter Avenue near Burkhardt Road for an auxiliary airport. The cost of construction was $63,000 and by June all private flying was diverted to this new airport leaving only military and commercial service conducted here. Organizations that operated there included: Evansville Flight Service, Culver Flying Service, and Midwest Air Transport. The Airport Board sponsored a contest for a $100 war bond as the prize for naming the new airfield. Jerry Newman (a nine year old) and Mrs. Edna Duncan, each submitted the same entry, Evansville Memorial Airport. This became the official name of the auxiliary field in January of 1944. This year also brought the first car rental service to the airport, U-Drive Service began when the Airport Board approved the operation of Mr. Drachman's Evansville truck rental service.

A new airport terminal complex opened in 1950 at a construction cost of $787,000. On October 11, 1950, the Evansville City Council passed an ordinance to change the name of Evansville Municipal Airport to the Dress Memorial Airport, in honor of Mayor Dress. The terminal was dedicated on Sunday October 29, 1950. The food concessions were retained by the Airport Board until September of 1951, when Wicks Associates took over the concessions operations. In 1951, there were 79 aircraft based at the airport; 25 owned by fixed base operators, 41 private, 12 company and 1 National Guard aircraft. The total airport property consisted of 467 acres, of which 347 were utilized for aircraft operations and the remainder was leased for agriculture.

The Airport Board entered into lease agreements for the first time in 1958. The parking lot was leased to the Airport Parking Company, a new hangar and two old hangars were leased to Cresent City Aviation, and additional land was leased to Charles Jamison for development. The Airport Board also agreed to sub-lease with Cresent City Aviation and Mead Johnson and Company for a hangar to house their corporate aircraft. In 1959, the Airport Authority District was created. The Dress Memorial Airport entered the jet age for the first time in 1959 with the arrival of Eastern Airlines jet-prop "Electras".