 On 17 December 2010, Chester expressed an interest in staying at Carlisle beyond the end of his loan contract, but the transfer window brought with it talk of Chester making a transfer to Championship club Hull City, with Hull manager Nigel Pearson going public on 3 January with his interest in the defender.The next day, Hull had a bid believed to be worth around £300,000 accepted by Manchester United, and Chester underwent a medical on 6 January.The transfer was completed on 7 January, with Chester signing a three-and-a-half-year contract.