Starting at Manchester United, he later went on to play for the likes of Hull City, West Bromwich Albion, Aston Villa and Derby County.

Chester helped Villa gain promotion to the Premier League after winning the 2019 EFL Championship play-off final.

Chester played at UEFA Euro 2016 where Wales progressed to the semi-final of a major international tournament for the first time in the team's history.

Although Derby pulled two goals back, United ended up winning the match 4–2, meaning that they won the tie 4–3 on aggregate and qualified for the 2009 League Cup final.

[8] On 2 February 2009, Chester joined League One club Peterborough United – managed by Alex Ferguson's son, Darren – on a one-month loan.

[11] On 18 September 2009, Chester joined Championship club Plymouth Argyle on a three-month loan along with his Manchester United teammate David Gray.

[12] However, in his third appearance for the Pilgrims, Chester suffered cartilage damage that would rule him out of action for 10–12 weeks, beyond the scheduled end of his loan spell.

[14] He made his competitive debut on 7 August, starting at centre-back in Carlisle's 2–0 home win over Brentford on the opening day of the league season.

[18] The next day, Hull had a bid believed to be worth around £300,000 accepted by Manchester United, and Chester underwent a medical on 6 January.

[23] Chester enjoyed a strong year in his second season at Hull, playing almost every game under managers Nigel Pearson and Nick Barmby in central defence, forming a successful partnership with Jack Hobbs.

[29] Five games into his debut season as a first-team player in the Premier League, Chester was ruled out for an initial six-to-eight weeks after pulling his hamstring against Newcastle United on 21 September 2013.

[35] On 29 July 2015, Chester joined Premier League club West Bromwich Albion on a four-year contract for a reported fee of £8 million.

[42] On 12 August 2016, Chester signed a four-year contract with newly relegated Championship club Aston Villa for an undisclosed fee, believed to have been more than the £8 million West Brom paid Hull.

[46][47] Chester began the 2018–19 campaign as a main stay of the team before he suffered a knee injury in January 2019 ruling him out of the remainder of the season.

[51] On 25 June 2020, it was confirmed that Chester had been released by Aston Villa, signing a contract extension to allow him to finish the Championship season with Stoke City before becoming a free agent.

[54] The season was suspended in March due to the COVID-19 pandemic and restarted in June with Chester extending his loan to cover the remaining matches.

He returned to fitness but was injured in the warm-up prior to the 4–0 home win over Accrington Stanley in January 2023 before making an appearance.