Not at the program but went to Pritzker for medical school.
As far as the living situation, the main consideration is really the wide dispersion of the clinical sites. When I was a student, most people lived in the Hyde Park area and a sizeable chunk - maybe 25% - lived in the South Loop or other neighborhoods surrounding the downtown area (as students, we would rotate at NorthShore, but we were also coddled and got a paid hotel room for the duration of the time we were up there, which you don't get as a resident). Hyde Park is a nice neighborhood, but for those wanting more of a "downtown vibe" with access to downtown amenities, you probably won't find Hyde Park all that exciting. Living further north will also shave a few minutes off your commute to NorthShore, but honestly I don't think this offers all that much of an advantage unless you're living north of downtown (e.g., Lincoln Park and the surrounding areas). At least when I was there, the drive to downtown and the South Loop area only took about 10 minutes from Hyde Park, so it's not as if you're going to be saving tons of time. With the addition of Lakeshore (and, thus, more time away from the academic hospital), there might be a bit more incentive to live closer to downtown than in Hyde Park.
Also keep in mind that living in South Loop and other areas closer to downtown can be quite expensive, particularly compared to Hyde Park.