If you like rankings, you can look at Niche. Pittsburgh is definitely a nicer place for young professionals than Cleveland. Weather is about even though snow accumulation is minimal in Pittsburgh and huge due to lake effect in Cleveland. I’ve lived in Pittsburgh and that was when it was much less of a tech and medical booming place. I’ve stayed in Cleveland quite recently and found it not really appealing and not offering the same kinds of nice neighborhoods around the campus or equivalent cultural experiences for the most part, though I have less experience with Cleveland than with Pittsburgh.
Surgically, it would depend on what area of surgery you are interested in. Technically, the Cleveland clinic ranks higher than Pittsburgh for general surgery, but not by much. Everything else has Pitt higher up, if you’re looking at Doximity Residency Navigator. But outside of ranking systems, the fact is that as a med student you’re not going to be in Cleveland clinic all that much, you’re going to be in the other hospitals. Whereas your exposure at Pitt to all their hospital system, which is enormous, provides absolutely incredible experience, both in medical school and residency. Both will be fantastic training I’m sure. Ideally you should visit both so you can decide for yourself.