Chester made his Premier League debut on 18 August 2013 at Stamford Bridge in a 2–0 away defeat to Chelsea. 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. After two months out injured, he made his return in Hull's 2–0 defeat away to Arsenal on 4 December. Chester scored his first goal of the 2013–14 season in the fourth minute of Hull City's Boxing Day match against Manchester United; however, he later scored a second-half own goal to give Manchester United a 3–2 victory. On 17 May 2014, he started in the 2014 FA Cup Final against Arsenal and scored to put his side 1–0 up, although Hull went on to lose 3–2. Chester played 28 times in 2014–15 as Hull had a difficult campaign and were relegated to the Championship, finishing three points from safety.