Awarded guernsey number 36, Chitty made his VFL debut for St Kilda in Round 11, 1936, against Fitzroy at Brunswick Street Oval.

On 25 July 1940, Chitty enlisted in the Second Australian Imperial Force[5] and was posted to the 2/9 Field Ambulance Convoy, initially as a Private before gaining the rank of Corporal.

All three served in the North Africa Campaign, Private Arthur Chitty with 2/23 Battalion and Ronald and Phillip with 2/2 Field Ambulance.

The medal, reputedly made partly from metal from a downed Japanese aeroplane, became Chitty's good luck charm for the remainder of the war.

[10] During this time, Chitty carried a fellow soldier who was dying of malaria more than 200 kilometres (120 mi) along the Railway,[11] partly for which, on 6 March 1947, he was awarded the British Empire Medal.

[12] 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.