Chitty returned to Corryong and was working on his farm when World War II was declared. On 25 July 1940, Chitty enlisted in the
Second Australian Imperial Force and was posted to the 2/9 Field Ambulance Convoy, initially as a
Private before gaining the rank of
Corporal. One of four brothers to enlist, Chitty was sent to
Singapore on 1 March 1941 and was stationed with the Australian General Hospital in
Malaya when he was captured during the
Fall of Singapore in March 1942 and reported missing on 26 March 1942 Chitty had three brothers, Arthur, Ronald, and Phillip, who also enlisted in the Army. All three served in the
North Africa Campaign, Private Arthur Chitty with 2/23 Battalion and Ronald and Phillip with 2/2 Field Ambulance. Arthur was killed in action at
El Alamein on 22 July 1942 while Privates Ronald and Phillip Chitty were taken prisoner by the Germans. They were repatriated in 1943 and visited their brother's grave in North Africa in September that year. During this time, Chitty carried a fellow soldier who was dying of malaria more than along the Railway, partly for which, on 6 March 1947, he was awarded the British Empire Medal. After being repatriated at the end of World War II, Chitty was aboard the
Largs Bay returning to Australia when the
1945 VFL Grand Final between
South Melbourne and
Carlton was being played. As Chitty's brother
Bob was captaining Carlton, Chitty organised a syndicate and bet everything they had (which was beer) on a Carlton win. In an upset, Carlton defeated South Melbourne, and Chitty enjoyed his beers. ==Post-war==