you're gonna love chicago!!maybe not the weather so much, but i moved here from arizona and love love love it.
researchassurus is right--you might not even need a car depending on what your commutes will be, but my boyfriend and i share a car and are both over 25 and we pay 130 a month. rent is a little steep in some areas, but some areas that are not as high end as others can run about 825 for a two bedroom [ukrainian village, logan square, and if you're a little braver, humbolt park--i only say this from experience] and if you can afford a couple hundred more, roscoe village is still pretty reasonable and super cute. [we pay 975 for 1.5 bedrooms] it sounds like you have a pretty sweet rent budget if you can snag a roommate. cost of living is a little high, but everyone just seems to figure out a way to struggle through it. but let me tell you, that car will cost a lot. you need a city sticker, some places make you have parking permits, and i don't care how observant of no parking zones you may be, you are bound to get a few tickets, and the city is truly evil about booting and towing.
my dad came out to az to help drive me out here, and we rented from budget rental vans, and they had a very reasonable rate, unfortunately, i do not remember what that rate is exactly, but i would recommend giving them a call.
hope this was helpful! and if you haven't already done this, you might get some good advise if you post on la vida crafty, too. a lot more people check that forum group more regularly and there's lots of chicago crafties!
good luck to you!