The airline had its roots as a regional air charter company in the form of Tradewinds Charters, formed in 1976, and using planes predominantly leased from parent Singapore Airlines serving leisure destinations. Scheduled services were introduced as Tradewinds Airlines on 21 February 1989 when it leased McDonnell Douglas MD-87 airplanes for services to six destinations: Bandar Seri Begawan, Pattaya, Phuket, Hat Yai and Kuantan from Singapore's Changi Airport and Tioman from Singapore's Seletar Airport. As the carrier matured, regional business destinations such as Jakarta, Phnom Penh and Yangon were added to its network, thereby broadening the airline's appeal beyond the holiday maker to include the business traveller.[citation needed] A major marketing overhaul was started in 1991, culminating on the 1 April 1992 by giving the airline its present name and logo as a new corporate identity [2].

The rebranded airline utilised up to 6 of the new Boeing 737-300s introduced just a year earlier. The mid-1990s saw two Airbus A310-200 aircraft in use and the expansion of services to India and mainland China. It was the first Asian carrier to offer handheld portable video-on-demand (VOD) inflight entertainment in the form of the digEplayer 5500, available on flights to China and India.