The 21-year-old left-sided defender has spent two loan spells with the Ayrshire outfit but is now looking for a new club after his contract at Stamford Bridge was ripped up by mutual consent.
Press Association Sport understands that Killie boss Kenny Shiels could offer him a third stint with the Clydesdale Bank Premier League outfit, although he faces competition from Hibernian manager Pat Fenlon.
As a free agent, however, neither side will be in a hurry to sign the player before Thursday night's transfer window deadline.
Gordon was snapped up by Chelsea from Leeds' academy side in 2007 but failed to make the leap from promising youngster to first-team regular.
Instead he was sent out on loan to various clubs, with temporary moves to Tranmere, Scunthorpe and Peterborough also featuring on his CV alongside his Kilmarnock stays.
The England Under-20 cap spent the first half of this season with Birmingham but was sent back to Chelsea after picking up a thigh injury.
However, manager Rafael Benitez has both Ashley Cole and Ryan Bertrand to cover the left-back slot and decided Gordon was surplus to requirements.