Southampton-born Colwill, 19, is expected to leave Stamford Bridge once Thomas Tuchel has signed defensive reinforcements, with the club in the market for new centre backs.
Colwill spent last season on loan in the Championship where he stood out for Huddersfield in their incredible push to the play-off final.
The Saints have had success in securing talent from Chelsea before, with right back Tino Livramento gaining rave reviews last season, alongside loanee Armando Broja.
And England Under-21 Colwill could now join them with the Blues lining up a number of defensive targets that would see his path into the first team blocked.
The departures of Antonio Rudiger and Andreas Christensen may have opened a space for Colwill to replicate Trevoh Chalobah's first-team ascent last season.
However, new owner Todd Boehly is hard at work lining up established replacements with a number of big names in the frame.
Sevilla's Jules Kounde has been linked for the past year, while Matthijs de Ligt recently emerged as a target, alongside Kalidou Koulibaly and former Blue Nathan Ake.
The uncertainty may come to Southampton's aid in their pursuit of Colwill, but the Blues may be weary after losing Fikayo Tomori and Marc Guehi last season.
Both defenders went on to excel at AC Milan and Crystal Palace, and after leaving for a combined £45million.
Now their departures have been deemed by many as bad business, especially given the exits of Rudiger and Christensen.