Chicago, beautiful Chicago. I think you know my biases.
Objectively, I think they are pretty comparable academically and reputationally. In otherwords, they are both solid, but I don't think they stand out in my mind. That may be the case for many schools and many "critics."
A thing to consider is the school's proximity to other medical schools. Some surgical specialties, such as ortho and plastics, tend to favor away rotators. (I have no specific knowledge of non-surgical specialties). Away rotations can be a headache, you must arrange and finance the travel and housing costs; so, living by a bunch of other excellent medical schools may be something to consider. In Chicago, prominent names include Northwestern, UChicago, Rush, UIC... I feel like I may be missing some... but you get the point. Anyway, this particular factor may be important to you if you do decide that you want to end up in the Midwest.