I went to med school in chicago and interviewed at a few programs. Our FM director told us the top 4 we MUST apply to in the area were Illinois masonic, west suburban, Macneal, and lutheran. I absolutely loved illinois masonic and if my fiance hadn't received a great job opportunity in Denver, that's probably where I would have ended up. The faculty were great, residents very friendly, and the curriculum seemed very flexible to pursue whatever you wanted. West suburban was definitely the program to go to if you wanted to work hard and get tons of OB and procedures. TONS and tons of OB. They also have a strong OB fellowship. As for the big name academic fp residencies, generally those wouldn't be at the top of my list. Rush Copley is not actually at the Rush main hospital (it is out in the suburbs), mostly IMG, and based on classmates' sub i experiences there it's not really a strong program. Loyola is misleading bc you are actually doing most rotations at county...which is a really interesting experience, but again, mostly foreign medical grads, not the strongest program (I did my sub i here if you have specific questions). UIC was a good program if you want international experience. I don't know too much about northwestern but we did receive a transfer from there into our program this year due to a variety of reasons (you can PM for more info if you want) MacNeal seemed like a strong program...It just wasn't for me.
Anyways, that's just my rough summary of all the programs, feel free to message me with with more questions and Good luck!