Hawkes was born in Windsor, Berkshire. He was named after the singer and comedian Chesney Allen. His father is the singer Len 'Chip' Hawkes, formerly with the 1960s band The Tremeloes. His mother is former actress/game-show hostess Carol Dilworth, who appeared in an episode of the 1960s version of "Randall and Hopkirk" called "For The Girl Who Has Everything", as well as the 1969 horror film "The Haunted House of Horror". Keely Hawkes, his sister, was the lead singer of 1990s band Transister, and is currently a songwriter based in Los Angeles. He attended Charters School in Sunningdale.