@VSGPeanut101, as you should know, the Metra Electric runs to Hyde Park, so getting to the Loop (downtown Chicago) isn’t hard at all.
And about half the dorms are pretty close to a Metra Electric stop. In fact, some of the dorms are closer to a Metra Electric station than to the campus (for some of the dorms, it’s faster to get downtown via the 19 minute train ride downtown than it is to walk to the west side of campus).
Also, not sure if they had it when you were there, but the U of C now has a bus service that runs from campus to downtown and on north to all the neighborhoods north of the Loop, so accessing most of Chicago is actually pretty convenient these days if you are a UofC student. In fact, some UofC students live in apartments on the North side and take the bus to school these days.