Leaving the country for the city, Chitty played for Sunshine in the Victorian Sub-Districts before being signed by Carlton.

Chitty's king hit of South Melbourne's Ron Clegg in the second quarter is seen as what triggered the succession of violent incidents that garnered the match its nickname.

After leaving Carlton at the end of the 1946 VFL season, Chitty spent several years in country Victoria as captain-coach of the Benalla Football Club in the Ovens and Murray Football League from 1947 to 1949,[6] during which time he led the goalkicking on two occasions.

He finished his playing career with Ringarooma in the North East Football Union;[8] and, in 1956, he kicked 105 goals for the season.

In 1947, while he was living in Benalla,[9] Chitty ("a good horseman and bushman")[10] starred as bushranger Ned Kelly in the critically panned feature film, The Glenrowan Affair, that was released in 1951.