Since the end of the season, the Blues' hierarchy have been making every attempt to generate funds in order to meet their obligations with FFP.
That has resulted in Kalidou Koulibaly, N'Golo Kante, Denis Zakaria and Joao Felix - the latter two who were on loan - all departing Stamford Bridge, with Edouard Mendy, Mateo Kovacic, Hakim Ziyech and Kai Havertz expected to follow before June 30.
Chelsea may also still sell Mason Mount to Manchester United, providing that they are prepared to weaken their stance over a transfer fee, but other options have needed to be explored.
Loftus-Cheek has represented a different option despite the 27-year-old proving to be a valuable squad member under a number of different managers.
During 2022-23, the academy graduate made 19 starts and six substitute outings in the Premier League, sometimes being required to deputise at right wing-back rather than his recognised central-midfield role.
However, with one year left on his contract and the Chelsea board preferring to recoup a transfer fee that would go down in the books as pure profit in the books over a renewal, an exit has looked likely.
According to Italian journalist Daniele Longo on Twitter, Milan are now in a position where they wish to progress with a deal worth in the region of €15m (£12.89m).
The proposed transfer has been delayed for a number of weeks due to the changes which were made to the setup behind the scenes at San Siro.
New incumbents in the chief roles in the boardroom were said to be wary of spending such an outlay on Loftus-Cheek, unlike previous technical director Paolo Maldini.
Nevertheless, almost three weeks on from the legendary defender's departure, it appears that Stefano Pioli will finally be able to add Loftus-Cheek to his squad.
Milan, who reached the semi-finals of last season's Champions League and have qualified for the 2023-24 edition, will soon have money to spend after the proposed exit of Sandro Tonali to Newcastle United.
Fellow midfielders Aster Vranckx and Brahim Diaz have also returned to their parent clubs, leaving Pioli in need to reinforcements as soon as possible.