In recent seasons, the Italian giants, who were managed at the time by Stefano Pioli, have frequently had contact with the Blues over a number of players.
Fikayo Tomori was the first player to make the switch to San Siro, and the defender has subsequently been followed by Olivier Giroud, Ruben Loftus-Cheek and Christian Pulisic.
Each of the quartet have either enjoyed a successful stint with I Rossoneri or are still making a positive impact in the starting lineup.
Milan have since replaced Pioli with Paulo Fonseca, who has left Lille to take on the role at the Italian giants, yet it appears that another move could be made for a Chelsea player.
Chukwuemeka has admirers at Milan
According to journalist Gianluca Di Marzio, Carney Chukwuemeka has a number of admirers behind the scenes at the 2023-24 Serie A runners-up.
Injury prevented Chukwuemeka from making a sustained impact at Stamford Bridge last season, the England Under-21 international having been part of Mauricio Pochettino's first two starting lineups before suffering a knee injury.
The 20-year-old would subsequently only make two starts and 10 substitute outings in all competitions, yet he continued to show his qualities during his many brief appearances.
A neat assist came during the 4-1 defeat at Liverpool in January, while he came off the bench to score a crucial goal during the 4-2 victory over Leicester City in the FA Cup quarter-finals.
However, Chukwuemeka failed to make an appearance after an 18-minute outing against Everton April 15, leaving him at somewhat of a crossroads.
How may Chelsea handle any interest?
With Chukwuemeka having a contract with the West Londoners until 2028, Chelsea do not necessarily have to be in any rush to make a decision.
Nevertheless, the player is less than four months away from his 21st birthday without having ever completed 90 minutes in a senior club game.
That is a remarkable statistic for someone of his obvious talent and one that will concern Chelsea in the short and long term.
Depending on how Enzo Maresca feels about the player, a loan move may be considered if the playmaker is in line to become a key part at a particular club.
Chelsea will only contemplate a sale if they are able to recoup in excess of the £20m that they shelled out two years ago.