I will be joining you at Ole Miss next year, and I think I might know where you're coming from. Even though I was raised in nearby Memphis, I went to undergrad at Rockford College, just west of Chicago, a town I spent many a weekends in. I can tell you that Oxford will be a big change from Chicago; in many ways, it might remind you of some of the nicer towns in the west suburbs of Chicago, or even Evanston in north Chicago.
Keep in mind that Memphis is only an hour away, so you can still get a bit of the big city feel, not to mention great blues and bbq. The campus is absolutely beautiful; the law school isn't as bad as you have probably heard; it is one of the larger buildings on campus, right across from the Grove (heard of it?) and all of the classrooms are fully wired for internet with plugins for laptops. They are finalizing plans at Ole Miss for a new law school; unfortunately, it won't be complete until after we graduate.
The Oxford Square, just east of the campus, has a great small town feel to it, with one-way streets, a big court house at the center and lots of great places to eat and shop. There are plenty of apartments throughout town, with many complexes clustered to the south on Old Taylor Road (where I just got a place) and to the north of the campus. Coming from Chicago, you will be amazed at how cheap apartments run in Oxford; there are several two bedroom places for under $500.
I went to the Open House; you didn't miss much, just an introduction by two faculty members, a few current students, the Dean, and a tour of the school and lunch at the top of the football stadium. If you need any more information, please feel free to e-mail me. firstname.lastname@example.org
. Hope some of this helps, and I look forward to meeting you!