The 28-year old spent a considerable amount of time with the Gills from 2001 until 2007 before moving to Millwall and then later stints with Wycombe Wanderers, Welling United and Dagenham & Redbridge but is keen on a return to Priestfield Stadium to again link up with manager Andy Hessenthaler.
"They (Chicago) said they would like to provisionally offer me a contract but they had a full roster. I would certainly put that on hold for the chance to play for the gaffer again," he told Kent Online.
"Hessy (Hessenthaler) has always been an inspiring character in my career.
"He is the first person I would contact and am just grateful for the opportunity to come and get myself fit.
"It's been a pleasure to work with Andy, Ian Hendon and my old team-mate Nicky Southall. I have come in and felt at home straightaway and still got a soft spot for the club."