Thanks for all your input. I ended up booking a room at the Best Western University Plaza directly. For the $10 extra it gives me the option to cancel if the trip falls through. There was a room available at the Orrington but $1,500 for one night was not really in our budget!
We will be driving. Interesting that you are suggesting The Homestead. It's reviews are mixed and don't seem to be as good as those for the Best Western. Any idea of what's going on in Chicago that weekend that is making it so difficult to get a 4 star hotel for under $325?
I'm looking at a PRICELINE EXPRESS hotel in Skokie/Niles/Evanston area. 3 stars with business center, pool, free internet and free breakfast for $133 for the night of July 11. (I was looking for a hotel in Chicago but for some reason there are very few rooms available that night and the ones that are available are priced through the roof)