The 22-year-old is one of several names being considered by Massimiliano Allegri, whose side are looking for fresh attacking options after a difficult opening to the campaign.
Corriere dello Sport reports that Napoli are weighing up a move, with the club mindful of financial restrictions and squad-list requirements.
Gittens has endured a frustrating spell since arriving at Stamford Bridge from Borussia Dortmund in the summer of 2025. Despite the significant investment, he has found the net only once in a Chelsea shirt and has struggled to establish himself in the first team.
His opportunities have been limited by injuries and competition for places. According to Sky Sport Italia, he has made only two appearances in the League Cup this season, totalling 55 minutes, and has yet to feature in the Premier League. An ankle injury has also kept him out since October.
Napoli's interest comes after Roma pursued the England Under-21 international during the summer. The Sun reported that Roma proposed an initial loan payment of around £2.6 million, with a potential permanent fee of approximately £34.5 million. Chelsea rejected the proposal because they wanted an obligation to buy rather than an option.
The Italian club may now explore a temporary arrangement of their own, particularly given the need to strengthen without committing to a major permanent fee.
Corriere dello Sport also identifies Monza striker Gustavo Varela as a leading target, while Napoli are assessing other options across the forward line and midfield.
Gittens would offer Allegri another option out wide, but any deal is likely to depend on Chelsea's willingness to let him leave and the structure of the proposed transfer. The club's decision may also be influenced by his fitness and whether he can force his way back into the first-team picture after the international break.
For the winger, a move to Serie A could provide the regular football he has struggled to secure in England. However, Napoli's reported interest remains at the monitoring stage, with no agreement or formal bid reported.