Tradewinds Charters, formed in 1976, was a regional air-charter company.
In its early years, it mostly used planes leased from Singapore Airlines, its parent company.
In late February, 1989, scheduled flights were introduced, using the Tradewind Airlines brand to serve six destinations with leased McDonnell Douglas MD-87s aircraft.
A major marketing overhaul started in 1991, reaching its peak in April, 1992, when the airlin got its present corporate identity.
After the rebranding, SilkAir used six new Boeing 737-300s, followed by two Airbus A300-200s that were added in the mid-1990s.
SilkAir was the first Asian carrier to ofer handheld portable video-on-demand entertainment, thanks to its DigEplayer 5500.
In 1998, SilkAir took delivery of the first Airbus A320-200 thus beginning to replace its Boeing fleet with Airbus aircraft.
In September 1999, SilkAir took delivery of its first A319-100 aircraft.
In 2002, SilkAir announced expansion plans to increase its fleet, the purchase of 4 Airbus 320s and 2 Airbus 319s, and services to destinations in India and China.
In 2004, SilkAir was recognized as the Best Regional Airline (Asia and China) by TTG Asia and TTG China magazine, and, in the Conde Nast Traveler Readers’ Travel Awards, ranked as the leading Asian carrier in the Leisure Travel – Short Haul category.
In 2006, the airline signed a SGD 2 billion agreement to acquire 11 Airbus planes, with nine more on option.
In 2012, SilkAir placed a firm order for the purchase of 23 Boeing 737-800s and 31 Boeing 737 MAX 8 aircraft, which will be used for the expansion of the airline and to replace the existing A319 and A320 fleet.
By May 2014, SilkAir received its first two Boeing 737-800 aircraft.
In 2015, SilkAir launched new routes to Cairns, in May, and to Malé, Maldives, in October. Cairns is the second Australian city in its route network, after Darwin, and the addition of Malé increased the number of destinations in SilkAir’s route network to 49 destinations in 13 countries.
In October 2016, SilkAir launched a new fast and intuitive mobile app, offering customers a functional and seamless user experience and greater travel convenience from booking to boarding.
In October 2017, SilkAir received its first Boeing B737 MAX 8 aircraft to operate a new route Singapore – Hiroshima, the only non-stop service between Singapore and Hiroshima, which is the first Japanese destination that SilkAir has added to its network. The MAX 8 aircraft features a new seat configuration of 156 seats – 12 seats in Business Class and 144 seats in Economy Class, the soothing Boeing Sky Interior, enhanced personal space with a 25% increase in seat pitch (39” to 49”) as well as additional seat recline (8” to 12”) in Business Class, and ergonomic aqua and light grey Economy Class seats fitted with seat-back tablets, phone holders, and personal in-seat USB charging ports.
In January 2018, SilkAir became the first to fly the new Boeing B737 MAX 8 to Australia. Currently, the MAX 8 aircraft is serving its launch destination, Hiroshima, and is also operated on other long-haul routes in the network including Bangalore, Hyderabad, and Kathmandu.
A single deadly incident involving SilkAir occured so far – in December, 1997, a Boeing 737-300 plunged into a river in Sumatra, killing all 104 people on board.