Ontario Express first started operations on July 15, 1987 as a regional feeder airline for Canadian Airlines based at the Toronto International Airport. This was a way to apply the newly designed commercial aviation strategy at the time: use smaller aircraft to gather passengers from various locations and "feed" the main airline which would then carry those passengers worldwide. The term "feeder airline" became a standard in all commercial aviation. The other term employed was a "spoke and wheel" type of organization, the spoke being the centre where all the feeder airlines would fly in the passengers from around the area. Operations started with 4 Jetstream 31 aircraft, manufactured by British Aerospace. ATR42 aircraft, built by a Franco-Italian consortium Avions de transport régional, were added to the fleet in 1988. Ontario Express was the first airline to import and operate those 2 aircraft in Canada. The first cities that were connected to Toronto were: Windsor, Sault Ste. Marie, Sarnia, London, Kingston, Thunder Bay, Ottawa, and Sudbury.
In January 1991, Canadian Regional Airlines was formed as a holding company to hold and manage Canadian Airlines International regional airline interests. At that time Canadian Airlines International acquired 100% of both of Time Air and Ontario Express as well as 70% of Inter-Canadien. In April 1993, Canadian Regional Airlines brought the operations of Time Air and Ontario Express together to operate as Canadian Regional Airlines. The two carriers were legally amalgamated in July 1998. In turn Canadian Regional Airlines was merged with other airlines into Air Canada Jazz in 2001.