Danny Drinkwater is in Istanbul, completing a loan move to Turkish Super Lig club Kasimpasa - and Chelsea will subsidise his salary to help complete the deal.
The 30-year-old has spent several months in the Blues' Under-23s squad after failing to find a move in the summer.
The Turkish top-flight has been targeted as a place for the £35 million ($47m) signing from Leicester to rehabilitate his career, having played just seven senior games in the last two and a half seasons.
The midfielder has eighteen months left on his contract and it is looking increasingly unlikely that Chelsea can recoup much of the fee paid in 2017.
Chelsea are on a wider mission to trim down their squad and offload players in January, with loanees being sold and a few of Frank Lampard's first-team squad on the market.
Milan have now asked for a £26m ($35m) option to buy as part of the deal, but Lampard is reluctant to sell the defender who he had on loan at Derby County.
“He absolutely has a long-term future at this club and we will see if and when he goes out on loan," Lampard told reporters ahead of his side's clash with Fulham.
"The moment I got close with Fikayo is when I took him on loan to Derby, and he was the player of the year and one of the best players in the Championship that year. He came back last year, played 20-plus games for us at a young age and then got in the England squad.
“There is a long-term plan for Fikayo in my head about his career here. If he goes out on loan, it will be to enhance his personal development, hopefully help the team he goes to, and come back as a better player.”
Chelsea have released Lucas Piazon and Charlie Brown from the loan group to permanently join Braga and MK Dons respectively, and are looking for solutions for other players outside the first-team picture.
It comes with FIFA set to impose limits on the number of over-23 players allowed on loan from next season.
Like Drinkwater, Baba Rahman is in talks with two overseas clubs about a six-month loan deal having trained with the development squad this season. He would then look for a permanent move away in the summer.
Chelsea could also loan out Marcos Alonso or Kepa Arrizabalaga, but their high salaries have led to little interest from cash-strapped clubs in the coronavirus pandemic.