I'll throw out a voucher on my own program, University of Illinois-Chicago (UIC), but will refrain from commenting or comparing it to other Chicago programs. I'm speaking from the perspective as an intern who matched there for next year.
I think that this is a program really on the way up. They have added new leadership in the past few years (program director, Dr. Gorelik, is a real asset...seems very resident friendly) and he has recruited a whole bunch of new faculty from around the area to strengthen the department. There is an excellent diversity of experience as you work in 3 different hospitals with exposure to phenomenal pathology; this is one of the strengths of the program in my opinion. There is the urban University hospital, the VA, and Christ, a large (700+ bed) community hospital on the South Side. You get to work in the role as the primary service (Univ. Hospital) or the consulting service (Christ). Most attendings are very dedicated to teaching. The department takes particular pride in its stroke and Neuro ICU training, as Dr. Gorelik and faculty have placed an emphasis on this. And no doubt one of the biggest strengths is the fact that it is here in Chicago, a great place both to learn medicine and to live. You can find anything in the city that you could possibly desire with regards to entertainment, dining, job opportunities for spouses, etc.
The program has also recently expanded in size, and now is taking 5 residents/year which apparently really helps with the workload. The personality of the program would probably be considered a more "clinical" one, meaning you work hard and learn by doing things and seeing lots of patients, and there is perhaps less emphasis on research. However, I am told that there are adequate opportunities to get involved with research if you choose, and many residents do. Everyone seems to place well into the fellowships of their choice, and I am told that roughly half of available fellowships in the department each year are filled by UIC residency grads.
Overall if you are looking for a diverse, clinically oriented program in an urban academic center in one of the greatest cities in the country, I'd consider UIC. Any specific questions let me know, and good luck with your interviewing...enjoy the free dinners!