Something unrelated

This decision is weighing heavily on my mind. I'm trying to consider pretty much all options I have...
So here's the decision: Should I move to Chicago to stay with 2 really good friends, and potentially start over and be able to pull myself from this crap shoot I'm currently in as far as finances, or stay in San Diego where I have a job, but just need to find a new place to live.
My roommate wants me to move out so that his friend can move in, I'm paying $750/month for my room. I wouldn't pay anything for a couple months until I got a job and got a little caught up if I moved to Chicago.
Unfortunately, I'd have to find another job. I'd also have to see what the healthcare in Chicago is like, for personal reasons =) Or maybe if I can keep my California residency somehow, claiming my address as being here still... Not sure if that'd work. I want to keep my Cali residency, honestly. Anyways: Job. So I'd have to get another job in this current job market. The minimum wage in IL is 7.75, only .25 behind California. But I make 11.55 ...
So I risk not being able to find another job, and leaving a job that I've got it pretty good at right now. Health insurance, dental, vision. Oh that reminds me, I need to get a cavity looked at... And if I found another job, it'd be another 3 months from the day I started working before I got benefits, if the job has benefits.
I'd also be leaving behind the last 3 years of my life to try something new.
I'm not sure if it'd work or not.
I'd still have to find another place here in San Diego by the 1st, which I'm not really -ready- to do. Ugh. I'm not ready to leave San Diego yet, not mentally at least.
I've still gotta figure out what to do about my turntables, my bike, my bed... If I have the money to ship my turntables....
I need to smoke.
Where's my fucking pipe...