Go ahead and call me crazy, but I think he could win. Yes, it will be tough, especially if Madigan runs against him, but he's still an incumbent, and if 2016 is a strong GOP year (which I doubt at this point), he could manage to hold on. After all, he is much more moderate and a better fit for Illinois than most Republicans.
That's fair, but you don't really see the minority party (in a state) hold onto too many Senate seats in presidential years any longer. It happens of course, but IL is a tough go and Democrats are likely to get 70% in Cook County with much heavier turnout than in '10. Kirk lost Cook 62-31% I believe which turnout down. The numbers just don't seem to really add up. If he had the name recognition and overall state popularity backing him, then maybe.
That being said, he is from the "collar", which is always the crucial swing areas of the state. So, who knows?