The 27-year-old has been frozen out at Chelsea this season by new manager Enzo Maresca, only making one Carabao Cup appearance while being left out of each of the side's Premier League matchday squads.
He was placed in the club's 'bomb squad' over the summer after being deemed surplus to requirements, but failed to get a move away from west London.
However, he may finally receive an escape route from Stamford Bridge in January as Napoli are interested in signing him, according to The Sun.
It is understood that the Serie A outfit are monitoring Chilwell, with former Blues boss Antonio Conte a 'huge fan' of the left back.
Chelsea's Ben Chilwell has been linked with a January move to European giants Napoli
A loan move could be the most likely outcome, with the option to make the transfer permanent next summer.
A number of Premier League clubs are also keeping a close eye on Chilwell, but he may feel a move abroad is his best option to get his career back on track.
The defender joined Chelsea four years ago and won the Champions League in his first season, but injuries and a loss of form has seen his career stall.
He failed to make England's Euro 2024 squad, and the last of his 21 international caps came back in March.
Yet a switch to Napoli could help him return to his best, with multiple former Premier League stars already starring under Conte in the opening weeks of the season.
Scottish pair Scott McTominay and Billy Gilmour moved to Napoli from Manchester United and Brighton respectively at the end of the summer window and have made promising starts to their time in Italy.
After losing their first game of the season 3-0 at Verona, Napoli have won five of their last six Serie A matches to open up a two-point lead at the top of the table.
They look set for a much-improved campaign this term under Conte, after enduring a disastrous 2023-24 season that saw them finish down in 10th and miss out on European football just 12 months after winning the league.
Napoli return to action on Sunday when they travel to Empoli.