Having first played for Kent's Second XI in the Minor Counties Championship in 1928, Chalk made his first-class debut of the county in July 1933 against Middlesex at the Bat and Ball Ground in Gravesend. Working as a teacher at Malvern College from 1934 to 1938, he played for the county on a fairly regular basis during the summer holidays each season until 1938 when he was appointed captain of the side. He played throughout the next two seasons, making a total of 101 appearances for the county.