=== West Bromwich Albion and Aston Villa ===

In August 2015, Chester signed for Premier League club West Bromwich Albion on a four-year deal. He made his debut for West Brom on 12 September 2015, in a 0–0 draw against Southampton. However, after just one season, Chester joined Championship club Aston Villa in the summer of 2016. He played a crucial role in helping Villa gain promotion to the Premier League after winning the 2019 EFL Championship play-off final.

=== Stoke City and Derby County ===

In January 2020, Chester joined Stoke City on loan for the remainder of the season. He made 16 appearances for Stoke before the loan was made permanent in August 2020. Chester played for Stoke City until July 2022 before joining League One club Derby County. However, his time at Derby was plagued by injuries, and he left the club in 2023.

=== Barrow ===

In September 2023, Chester signed a deal with League Two club Barrow. He joined the club as a centre-back and will be looking to make an impact in the upcoming season.

=== International Career ===

Chester made his international debut for Wales in June 2014. He represented Wales at UEFA Euro 2016, where the team reached the semi-finals, marking a historic achievement for Welsh football. Chester has been a valuable asset to the Wales national team and has made numerous appearances for his country.