Trans Caribbean Airways History: New York to San Juan – Airline Employee Shop

Trans Caribbean Airways History

Trans Caribbean Airways grew from a postwar charter outfit into a New York to San Juan jet airline, then joined American Airlines in 1971. Here's a short history of Trans Caribbean, plus the Trans Caribbean Airways collection that celebrates it.

A postwar "non-sked" (1945-1957)

O. Roy Chalk incorporated Trans Caribbean Air Cargo Lines in New York on May 18, 1945. It started flying that December with war-surplus Douglas DC-3s. Like hundreds of postwar "non-skeds," it flew as an irregular carrier, first hauling cargo and then low-fare passengers between the mainland and the Caribbean. Chalk ran the airline for its entire life.

Scheduled service to San Juan (1957-1961)

In 1957 the Civil Aeronautics Board certificated Trans Caribbean as a scheduled international airline. It was the only supplemental carrier to win that status in the regulated era. Scheduled New York to San Juan flights began in March 1958, using DC-4s and DC-6s. In 1959 it launched "Golden Troubadour" weekend DC-6 flights, with a dance floor and live entertainers on board. Aruba joined the network in 1960.

The jet years (1961-1971)

Douglas DC-8 jets arrived in late 1961, and stretched DC-8-61s followed in 1967 and 1968. The airline added Washington Dulles in 1967 and took its first Boeing 727 in 1968. In 1969 it added St. Thomas, St. Croix and Curacao. It was known for low fares on the New York to Puerto Rico route.

Joining American (1969-1971)

At the end of the 1960s Chalk agreed to sell the airline to American Airlines. After approval by the CAB and the President, American took over in March 1971. Within months American was the leading carrier between New York and San Juan.

A few things collectors love

  • Golden Troubadour: the 1959 "night club" flights to San Juan, complete with a dance floor.
  • "Your Flying Island," the slogan printed on its 1968 system timetable.
  • A true underdog: one of the only charter airlines of its era to become a scheduled carrier.

Shop Trans Caribbean Airways

Browse Trans Caribbean Airways logo T-shirts, coffee mugs, coasters, tote bags and vintage designs in the Trans Caribbean Airways collection. Add an airline bag tag or key tag, or explore the rest of the AA Family Tree collection.

AirlineEmployeeShop.com sells Trans Caribbean Airways merchandise under license from American Airlines. This page is for historical interest.