I really wanted to be in Chicago for residency, so I actually did two. I dont know if that's necessary (or if most people have room in their schedule to do that), but it did give me good exposure to two different programs. I spent one month at Northwestern and one at Loyola. Northwestern has a good program and some of the best facilities out there. The problems with the rotation is that 1) a larger number of visiting students rotate there, so it's more difficult to get some good face time with the faculty on a regular basis and you will end up doing floor work on some days without even seeing a faculty member, 2) the faculty will usually take only student with them in the clinic per day, so you are somewhat limited in getting to know them well if there are others around, and 3) as a visiting student, you will only rotate at Feinberg downtown, even though residents rotate at Evanston, Children's in Lincoln Park, and Cook County- so, you will not necessarily get a completely accurate feel of the entire program.
I also spent a month at Loyola, which I felt was a much better rotation- that is, I felt that my time spent there was more productive. They structure the elective for visiting students specifically so that you spend one week dedicated on each service. They specifically split up students, so that you're not on the same service with any other visiting 4th years. Also, they have clinics (e.g. at the VA) that are purely for teaching and are more relaxed, so that you get to spend a lot of quality time with the faculty- I felt that they got to know me really well by the end.
As far as the other Chicago programs go, I don't really have much info. Hope this helps.