Chilwell underwent a scan on Thursday on the hamstring problem that forced him off in the closing stages of the EFL Cup win over Brighton, with the manager confirming it "looks a bad injury" though he was unable to put a timescale to it.
New club captain James has not played since the 1-1 draw with Liverpool on the opening weekend of the Premier League season, and will not be fit to return before the next international break.
Both players missed significant portions of last season through injury, Chilwell playing 23 times in the league and James only 16, a contributing factor to Chelsea's worst finish in 30 years.
Malo Gusto has deputised for James but will miss Monday's game at Fulham after being red-carded against Aston Villa.
Marc Cucurella, Levi Colwill and Axel Disasi are all able to play at full-back but the manager said no deputy can be expected to bring what James and Chilwell do to the side.
"At all clubs, important players are missed when they don't play," he said. "If the question is 'do we miss them?' Of course. Reece is a top player and (Chilwell) also. When they're at their best, they are the best full-backs in the world.
"But all teams when they miss important players are affected (in their) performance. Why did we not sign another Ben Chilwell and another Reece James? Because there's only one Reece James and one Ben Chilwell.
"If you have in the squad one top player in one position, it's difficult to bring in another one in the same position to sit on the bench. It's about balance."
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