The airline had its roots as a regional air-charter company as Tradewinds Charters formed in 1976, and using planes predominantly leased from parent company 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 6 destinations: Bandar Seri Begawan, Pattaya, Phuket, Hat Yai and Kuantan from Singapore's Changi International 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.
SilkAir A319-100 at Singapore Changi Airport, with a Singapore Airlines (parent company) Boeing 777 in the background.
A major marketing overhaul was started in 1991, culminating on 1 April 1992, by giving the airline its present name and logo as a new corporate identity. The re-branded airline utilised up to six 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 as well as mainland China. It was the first Asian carrier to offer handheld portable video-on-demand (VOD) in-flight entertainment in the form of the DigEplayer 5500, available on flights to selected countries.