So, in reading
@DopeyBadger 's thread, he has the hotel info in there for Chicago. So, if you look at some of the websites directly, they show no availability, but I'm guessing that's because they are blocked out for the official race accommodation process. Sound right? So, if you really want to stay at a particular (and likely popular) hotel, is it better to just go ahead and book something now even without knowing if you are in? It looks like you can cancel without penalty easily enough. And, yes, I'm really asking this question right now.
If we end up getting in, I think we would make this an extended weekend trip anyway. We love Chicago regardless and it's a great excuse to make it a running vacation.