Chesters signed professional terms with the Club in the summer of 2020, before his progression would see him rewarded with a new contract in early 2022.

The wide midfielder made his first team debut as substitute in the UEFA Europa League group stage home win over KRC Genk in October 2021, and the Premier League away clash against Liverpool.

Summer 2022 saw Chesters loaned to EFL League Two club Colchester United, for whom he made 18 appearances in all competitions and registered two assists, before returning to West Ham in January 2023.

Upon his return, Chesters was utilised as a wing-back in the side, and ended the campaign with 16 appearances in all competitions for the development team.