It was founded in 2014 by local businessman Ewan Wilson, who previously was the CEO of Kiwi Travel International Airlines, and commenced operations on 27 October 2015.

[3] In February 2015 the airline revealed its proposed route network, planning to serve Auckland, Hamilton, Tauranga, Palmerston North, Wellington, Blenheim, Nelson, Queenstown and Dunedin.

However, the government rejected the airline's plans to operate commercial flights from the base, citing a 2009 decision for it to remain as a military-only airfield due to concerns from local residents about noise.

[5] On 24 June 2015, Kiwi Regional Airlines released an amended route network, that would see it initially serve four destinations using a single aircraft, with flights planned to commence on 27 September 2015.

[13] Flights from Nelson to Christchurch were announced in early 2016, but were cancelled in May 2016, in tandem with a reduction in frequencies across other routes due to reduced demand over winter.