The Tigers' defence is the best in the bottom half of the table thus far in the campaign, and they have strengthened up front this transfer window with the acquisitions of Shane Long and Nikica Jelavic.
However, Steve Bruce confirmed the blow that Chester had suffered damage to the hamstring that had kept him out for three months earlier in the season.
"James has damaged the tendon again, the one that he damaged at the start of the season," said Bruce.
"It's not as bad as it was the first time he did it, but it's still a concern because it is the same tendon high up in his hamstring."
Bruce stated that it is a big blow for a player that was just starting to get back into the side following his previous setback.
"He's going to be at least six weeks away I would have thought. It's a shame because he was just finding his feet again after his last spell out, but that is football," added Bruce.