The midfielder spent just under 20 years at the Blues in which he rose through their academy ranks and into the first-team picture.
Loftus-Cheek enjoyed an excellent 2018/19 campaign before an achilles injury prevented his Chelsea career from really taking off.
He failed to stake his claim as an important player for the side after his injury and left for Milan in June, a move that's proven beneficial.
The ten-cap England international has started in six of their eight Serie A matches this season and it's clear that Loftus-Cheek is enjoying his football out in Italy.
"At Chelsea I felt like a caged animal," he told La Gazzetta dello Sport. "I didn't play as much as I wanted and when it happened I played in positions where I couldn't express myself.
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"Here, however, I have a free mind, I play as a midfielder as I like and it's like being a child again, when we played without worries.
"If the whole team has this feeling, great things can be achieved: even winning the championship. We feel like the best."
Loftus-Cheek, a natural midfielder, featured at right wing-back for Chelsea, doing so under the reign of Thomas Tuchel.
The German also opted to play him at centre-back in their FA Cup fifth round tie away at Luton in 2022.
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During his Blues career he had spells on loan at Crystal Palace and Fulham before moving permanently to Italy in the summer.
Since then he has scored one goal and assisted another two, with the 27-year-old already feeling right at home in Milan.
Loftus-Cheek is also joined by three other former Chelsea stars in the Italian city in Olivier Giroud, Fikayo Tomori and Christian Pulisic.