Designed to succeed the De Havilland Tiger Moth biplane trainer, the Chipmunk flew for the first time at Downsview, Toronto on 22 May 1946. It was the first indigenous design of de Havilland Aircraft of Canada Ltd. The prototype was powered by a 108-kW (145hp) de Havilland Gipsy Major 1C
Two were evaluated by the Aeroplane and Armament Experimental Establishment at Boscombe Down. As a result, the fully-aerobatic Chipmunk was ordered as an ab initio trainer for the Royal Air Force. Prince Philip took his first flying lesson in one in 1952. The Royal Canadian Air Force also adopted the Chipmunk as their primary trainer. British Chipmunks are notably different from Canadian ones; the latter have a bubble canopy, while British examples have the flat-panelled sliding canopy.
The RAF received 735 Chipmunks manufactured in the UK. They initially served with University Air Squadrons. A few Chipmunks were pressed into service in Cyprus on internal security flights during the troubles of 1958, and some were used for covert reconnaissence operating out of Berlin. They were still in service for Air Cadet Experience flights until 1996. The last two Chipmunks in military service are operated by the RAF Battle Of Britain Memorial Flight, to keep its pilots current on tailwheel aircraft.
Downsview built 218 Chipmunks, the last in 1951. 1014 were built in Britain. 60 Chipmunks were licence-manufactured from 1955 in Portugal for the Portuguese air force. Other users included Burma, Ceylon, Chile, Colombia, Denmark, Egypt, Eire, Iraq, Israel, Jordan, Lebanon, Malaya, Saudi Arabia, Syria, Thailand and Uruguay.
From the 1950s onward, the Chipmunk became a popular civilian aircraft, being used for training, aerobatics and crop spraying. Most civilian aircraft were ex-military.