He moved to the Wigan Warriors in 1999 and played from the interchange bench in their 2000 Super League Grand Final defeat by St. Helens.

He also played for the Wigan Warriors from the interchange bench in their 2001 Super League Grand Final defeat by the Bradford Bulls.

Chester then moved to Hull FC, and played in the 2005 Challenge Cup Final from the interchange bench in the victory over the Leeds Rhinos.

In his first full season as head coach Chester guided Hull Kingston Rovers to the 2015 Challenge Cup Final, but his team were soundly beaten.

On 10 August 2021, Chester was terminated as head coach of Wakefield after recording only four wins in the 2021 Super League season and with the club sitting second last on the table.