What if your car breaks down? As much as you might not want to use it, Chicago has pretty decent public transit. Forget the idea in California, where the financial situation has been worse than most anywhere else in this country. California is a tourist state, and if you're not a tourist bringing them money, you're not going to get a great reception.
I lived there over ten years. Do your homework again, because unless you're young and very attractive entry-level jobs won't be easy to get. If you don't have good connections of some sort, no job will be easy to get.
People with dreams AND a bankroll and time have been going to California for over a hundred years, and the vast majority ended with nothing.

You've been slammed by two traumas in the past few months:
--a devastating auto accident
--your child's transfer of a primary bond and home with you to one with a girlfriend (possibly sexual partner)

Add in around this the probation at work, the lousy state of the world, your mom's family "gentle demands" ...

Doing a geographic right now because of your childhood dream seems really tempting fate ... several leaps beyond merely taking a chance. I don't think you're in a stable-enough mental state, recovered sufficiently psychologically from the effects of the auto accident, to make such a huge decision.

I also think much--too much--isn't decision but reaction to your son's decision. Give yourself time to make some of the natural transition from "mom" to "friend" that will come once the relationship begins to evolve. This can turn into an exciting an happy time.

Take some deep breaths. Maybe talk with your mom?

Please, above all, slow down. The speed is largely what suggests you might be re-acting as much as deciding. This can all be okay. Slow down. Look at everything more thoroughly. Okay?

Roadie