The airline was founded by Arthur Burns "Pappy" Chalk, and started "ad-hoc" charter operations as the Red Arrow Flying Service in 1917 flying a floatplane. After "Pappy" Chalk served in the Army Air Service in World War I, he returned to Miami and commenced scheduled service between Miami and Bimini in the Bahamas in February 1919 as Chalk's Flying Service. Chalk's first base was a beach umbrella on the Miami shore of Biscayne Bay. In 1926 a landfill island, Watson Island, was created in Biscayne Bay close to Miami. Chalk's built an air terminal there, and operated from the island for the next 75 years.