Hi all, I've since found great housing with a great roommate... After scouring the city for the best options, my advice is this: the Lakeshore area is best, anywhere near the redline. Wrigleyville is amazing, young, lively, attractive area, whereas Rogers Park is much more quiet and 100% residential. I guess it depends what you're looking for. DON'T even attempt to look south of downtown or anywhere more than a mile west of the lake. There's shady areas out there.... meanwhile there's thousands of student friendly apartments within the few miles south of the Lakeshore campus, and the redline El (elevated train) drops you right on campus.
Online housing sites only tell you so much, I've found that stepping foot on the premises often reveals what the websites were hiding... The best part about the Lakeshore/Rogers park area is that you can walk around for 10 minutes in any given residential area, and pass 20 For Rent signs, most of which are not listed online. You could easily find a place in a day if you aren't too terribly picky if you go M-Th and call the landlord's numbers, the vast majority of them were super nice, prompt, and helpful.
If you have any questions, about housing or about the program, feel free to PM me, I'll be happy to answer as best as I can. 🙂