He started playing the guitar at age twelve when he was living with his grandfather, Harry Purdy, on Moloka'i.

After high school, Chillingworth moved to Honolulu and joined Pahinui, Andy Cummings and others at clubs, lu'aus and all-night jam sessions.

Many islanders and tourists enjoyed listening and watching him sing and play his guitar in the Don Ho Shows[2] at the International Market Place in the heart of Waikiki.

In the 1970s, Chillingworth began to share his knowledge with younger performers, such as George Kuo, Ozzie Kotani, and Makana,[3] and influenced others through his recordings.

Chillingworth helped lead a revival of the slack-key guitar style in the 1980s as one of slack key's elder statesmen.