 Chester was an ever-present in 2017–18 playing in 50 matches as Villa reached the 2018 EFL Championship play-off Final but lost 1–0 to Fulham.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.In his absence Villa again reached the play-off final where this time they were successful, beating Derby County 2–1.