I asked this to someone via PM, and my apologies if it's been asked before, but where would you guys recommend around the $900-$1000/month price range that is still close to the Law School via transportation (presumably for my 2L/3L years)?
And also, since HP seems to be the cheapest/most convenient option during your 1L, is this where most stay? Is this where you guys would recommend a 1L stay? How safe do you feel walking around HP after midnight on a Saturday?
Anywhere in Hyde Park has pretty easy access to the law school. There are plenty of places in Hyde Park in that price range for a 1BR, but most 1BRs in other neighborhoods will run $1400+ per month. If you're thinking about taking a roommate, you should be able to find something in that price range in most neighborhoods in the city. South Loop and the Loop have the best public transport options to the law school outside of Hyde Park (mostly the 2 bus, but I think the 4 will get you close enough).
Most 1Ls live in Hyde Park, although its not a requirement. It's nice for 1L because it's where most of the social scene is and it's very convenient and reduces commute time.
Walking around at night depends on where you are exactly and who's travelling. Group of people with multiple men, you're fine. Single girl, bad idea. There are several good options for travelling at night though - safe ride (free university taxi service within Hyde Park), a night shuttle system, and the police will trail you if you're on foot and you call them.