housing woes

So, for the first time ever in Chicago, I may be having a hard time finding an apartment. I'm pretty sure every previous time I've looked for a place to live-- which has been an unfortunately large number of times; this will be my sixth apartment in four years and my fourth in the last two alone-- I've ended up in the first place I've looked (or a girlfriend's house, but that's another story). But now I've decided the time has come to live by myself, which it turns out is a very expensive decision. I knew it would be, but here's something irritating: a place will be posted on craigslist, saying it's, say, $491, which would be fine. But when I call or, more frustratingly, show up, I'm informed that the apartment is somewhere between $550 and $640 or so. WTF??? So tomorrow I'm dropping off an application for a place that's $585 a month, which is possible but certainly not ideal. It is a nice studio, and closer to my job than anything else I've seen, but still more expensive than I was naively hoping for.
The other side of the coin is the process of subletting. I couldn't find our lease until tonight (tiny apartment+lots of crap and particularly a lot of papers=inability to find stuff), and lo and behold it says we have to give 45 days notice before subleasing. (We also have to pay $150, which is of course not wonderful but at least doable.) I'm hoping and praying that this is solely there so they can find a replacement and that they won't enforce it. Because I posted the apartment this morning, and lo and behold I've already had two people see it and probably at least three more in the next few days. Plus I'm betting at least one of the people tonight will bite anyway, so it's probably going to be the easiest part of the whole damn process. Unfortunately, it leaves me with a probably rented apartment (at least, if the landlords okay it) and no place to actually move into as of yet. Great. I keep hoping I can just fast-forward a few weeks (except for my upcoming trip home to Flagstaff, where I will hike and go shopping with my mom and see Ani diFranco in my hometown with my oldest friend) and have this all resolved.
Sorry for the rant. It's been kind of a hard few days.