Chesson was born in Adelaide and was educated at Grote Street Model School and Pulteney Street School. He began working in a boot factory at the age of twelve, and left school at fifteen to become a mason and bricklayer. He worked in Melbourne from 1885 to 1892 before returning to Adelaide. He was president and financial secretary of the South Australian Masons and Bricklayers' Society, and was their delegate to the Trades and Labour Council, of which he was also president and vice-president. Chesson also served on the Adelaide Trades Hall management committee and Eight Hours Committee, and as president and vice-president of the United Labor Party.
