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The England full-back damaged his anterior cruciate ligament in Chelsea's 4-0 Champions League win over Juventus on November 23.
The Blues had hoped Chilwell could return to action without surgery, but the former Leicester star is now due to have the ligament repair operation.
A statement issued by Chelsea read: "After a knee injury in the match against Juventus the Chelsea medical department, in collaboration with their knee specialist, took the decision to attempt a conservative rehab approach.
"Unfortunately Ben was unable to progress and so collectively the decision has been taken to proceed this week with a surgical repair."
Chelsea could look to the transfer market to bolster their Premier League title bid in January, with Everton's Lucas Digne strongly mooted as an option for the Blues.
Marcos Alonso is Chelsea's sole frontline left wing-back in Chilwell's absence, leaving boss Thomas Tuchel having to shuffle his resources for alternatives.
Callum Hudson-Odoi, Saul Niguez and Christian Pulisic have deputised without yet appearing fully comfortable in the role.
Chelsea could also look at recalling either Ian Maatsen or Emerson Palmieri from their loan spells.
Maatsen has impressed at Coventry in the Championship, while Emerson has been a regular in his temporary stint at Lyon.
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