Operations started on 27 November 1940 with a piston powered Lockheed Lodestar twin engine aircraft on daily services between Trinidad and Barbados.

Vickers Viscount four engine turboprops were introduced in 1955 with Bristol Britannias leased in 1960 to fly the long-haul route to London, via New York City.

For BWIA the jet age began in 1964 with the introduction of new Boeing 727-100 jetliners billed as the Sunjet,[6] which replaced the Viscount turboprops on the New York route.

According to its timetable, in 1968 the airline was operating nonstop Boeing 727 flights from New York to Antigua with continuing no change of plane 727 service to Barbados, St. Lucia and Port of Spain as well as nonstop 727 flights from Miami to Grand Cayman and Montego Bay with continuing no change of plane 727 service to Kingston, San Juan, Puerto Rico, Antigua, St. Lucia, Barbados and Port of Spain, and was also serving Caracas, Guyana, Suriname and Tobago with the 727.

[7] In early 1971 four second-hand Boeing 707 series 200 airliners were purchased from Braniff International Airways and operated on US and intra-Caribbean services until their disposal in late 1975.

On 22 February 1995, the government of Trinidad and Tobago completed the privatisation of BWIA by turning over majority control of the common stock and management of the airline to a private group of US and Caribbean investors.

In the early 2000s (decade), BWIA changed its livery to a new Caribbean green and blue color scheme with its famous steelpan trademark, the national musical instrument of its home base.

The fleet had been upgraded to seven Boeing 737-800 Next Generation aircraft, two Airbus A340-300s, and two Bombardier de Havilland Canada DHC-8 Q300 Dash 8 twin turboprop regional aircraft flown by BWIA's sister airline Tobago Express, which provided service on the short hop between Port of Spain and Trinidad's sister island Tobago as well as other destinations in the region.

BWIA also had an alliance with another Caribbean airline, LIAT, with both carriers providing combined service to over 30 regional destinations.