Right so, very few people seem to be taking into consideration just how many of us are students. At least, that is what the poll says. Fall semester 2009 my classes start on the 13 of August. After checking a whole bunch of schools' academic calendars, this seems to be around the most popular weekend to begin classes. So I am going to say that on behalf of everyone else, anything after that is right out.
And while you might think that Labor Day weekend (that last option) would work, it won't. Labor Day is one of the worst times to travel anywhere, and is one of the worst times for canceled flights and delayed trains and traffic jams. Any of you who would be leaving monday afternoon or night sometime to get back to work on tuesday should consider taking an extra day off from work for the very likely scenario in which you get stuck somewhere between Chicago and home, wherever that may be, in the event that we choose this weekend. This is, of course, assuming that no one else cares that Dragon*Con is Labor Day weekend as well, but since I understand that no one really gives a damn as to whether I personally am there for ChicagoCon or not, it doesn't really matter, unless you wanted to try and make it to D*Con next year.