Obviously, I'm biased, but Olympia Fields has done an annual golf outing to raise money for the Olympic games. I'm sure it would at least make it a contender in 2016.
As for Chicago getting the Olympics, it's pretty much a done deal that the IOC will come back to North America, which leaves us and Rio. Chicago would enable the entire US to see the games live, which would mean it would be the highest rated Olympics of all time. Remember, by the time they vote, anti-American sentiment should be waning as Bush will no longer be President. If Obama is president, I think it makes it even more likely.