I currently live in Chicago and am planning to move closer to the campus. I live in the Near North neighborhood now, and I don't want to mess with public transportation when I start class. I would suggest already having some properties you want to view when you are here in June. There are some free services that help you find apartments and, of course, do-it-yourself hunting like Craigs List.
When I moved here a few years ago from Baltimore, I came up on Memorial Day weekend, looked at some properties, and signed a lease for that August. If you start early, you can get what you want and not have to stress. This strategy works well with large buildings that have lots of units, but if you want a walk-up, you may have to do things a little closer to when you want to move. Either way, it is probably a good idea to have what you want in mind.
