[2] In 2020, Chester played for the Townsville Brothers A-Grade side before signing for the North Queensland Cowboys.
[3] In 2021, Chester joined the Cowboys' Young Guns squad and played for the Townsville Blackhawks Hastings Deering Colts side, starting at lock in their Grand Final loss to the Wynnum Manly Seagulls.
[4][5] In the 2022 pre-season, Chester joined the North Queensland NRL squad and played in their trial win over the South Sydney Rabbitohs, making the move to fullback.
[9] In round 18 of the 2022 NRL season, he made his first grade debut off the bench against the Cronulla-Sutherland Sharks.
On 20 December, the North Queensland club announced that Chester would miss the entire 2025 NRL season after he tore his ACL at a training session the week prior.