The airline maintains its headquarters at Wilson Airport, within Nairobi, Kenya's largest city and the country's capital.[4] Wilson Airport is located approximately 5 kilometres (3 mi), by road, southwest of the city centre.[5]
The airline maintains a private building at Wilson Airport, for the exclusive use of Skyward Express staff and clients. The building is "equipped with a modern cafeteria", among other amenities.[6]
Skyward Express was established in 2013, by two pilots; one of whom serves as the chairman of the airline, while the other serves as its managing director. Skyward Express inherited some equipment and some routes from the defunct Skyward International Aviation.[2]
With the cessation of service by Skyward International Aviation, Skyward Express began commercial operations in 2013. Initially, the airline offered passenger charter and cargo service between Nairobi, Kenya, and destinations in neighboring Somalia. These services included the shipment of miraa from Nairobi to Somalia.[2]
With the acquisition of more aircraft, the airline has expanded and diversified its passenger and cargo service to include more destinations and frequencies to oil-rich northwestern Kenyan counties and coastal tourist attractions.[2]
On July 21, 2021, a De Havilland Canada Dash 8-100 registered as 5Y-GRS crash-landed at El Wak, Kenya when its landing gear collapsed.[citation needed]
