Despite his senior status under Mauricio Pochettino, the left-back has dropped down the pecking order under successor Enzo Maresca.
There was a time during the summer when Chilwell had been banished from the first-team ranks ahead of a potential exit from Stamford Bridge.
However, the Blues hierarchy were unable to attract a suitable offer for the 27-year-old, resulting in him being reintegrated back into the squad earlier this month.
Although Chilwell is yet to be named in a Premier League squad, he did play the second half of the 5-0 victory over Barrow in the EFL Cup third round last week.
Has Maresca changed stance?
The major downside for Chilwell right now is being left out of the squad for the Europa Conference League, where he could have plausibly made six more appearances before the end of the year.
Instead, he is realistically looking at his next outing coming away at AFC Wimbledon or Newcastle United in the EFL Cup at the end of the month.
According to The Mirror, there are no plans for Maresca to have a complete change of heart over Chilwell's future.
Offers will allegedly be encouraged for the player in the first month of 2025, Chelsea still in a position where they would ideally like to improve their position with the Premier League's Profit and Sustainability regulations.
Chilwell still has a contract until 2027, but there is no prospect of a renewal under the current setup at the West Londoners.
What did Maresca say on Chilwell last week?
At a press conference last week, Maresca was quizzed over whether he had any regrets on the situation having effectively removed Chilwell from his plans within weeks of his arrival.
He told reporters: "We all make mistakes. Probably yes; probably no. I am here to take decisions. Sometimes they are good decisions and sometimes they are not good.
"The only thing I can say is that there is not any bad intention from me. It is just to see things and try to think about the best things for the club."
Marc Cucurella and Renato Veiga are the players currently ahead of Chilwell in the pecking order.