Chester, born on January 23, 1989, in Warrington, England, began his career at the youth academy of Manchester United. He made his professional debut in 2009 while on loan at Peterborough United. From there, he went on to have successful spells at Hull City and West Bromwich Albion before joining Aston Villa in 2016. After three seasons at Villa, Chester signed with Stoke City in 2019 before making the move to Barrow AFC in 2021.