First of all I again want to reiterate that I doubt Chicago moves Cutler. I am doubtful they will since like the Jets they have nothing at Qb after him, but if they find a way to be comfortable playing someone else, there is a case for moving Cutler. WIth the Revis signing, the problems at Qb remain as the single biggest hurdle between where the Jets were last year and the playoffs. The Revis signing also means the Jets D is now probably better than Buffalo's, so the idea Cutler would fit there better is imo not the case. I don't know how to quantify the NY media angle. Chicago after all has a media concentrating on a single NFL team, and it is an active media market.
And he has the arm to cut through the wind off the lake. Cutler has one of the best arms in football.