 On 3 August 2010, Chester joined League One club Carlisle United on loan until 3 January 2011, after impressing in a trial match against Hibernian on 1 August.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.Over the course of his loan spell, Chester scored four goals for Carlisle in 23 appearances in all competitions, including the winning goal in Carlisle's 3–2 FA Cup second round win over Tamworth.