Chester joined Aston Villa in 2016. He was signed from West Bromwich Albion for a fee of £8 million. Chester made his debut for Villa in a 1-0 defeat to Sheffield Wednesday on 7 August 2016. He scored his first goal for the club in a 2-1 win over Bristol City on 13 September 2016.
James Chester Smarty-Pants Showdown: 29 Questions to prove your intelligence