Chesley signed with the Houston Texans' practice squad on October 29, 2019. He signed a reserve/future contract with the team following the season on January 13, 2020. He was waived during final roster cuts on September 5, 2020, and re-signed to the practice squad two days later. Chesley was elevated to the active roster on December 12, December 19, and December 27 for the team's weeks 14, 15, and 16 games against the Chicago Bears, Indianapolis Colts, and Cincinnati Bengals, and reverted to the practice squad after each game. His practice squad contract with the team expired after the season on January 11, 2021.
