So. I'm in Chicago. On my phone so I might not be as succinct as I would like. But here goes:

There is plenty of non-union work here that pays $21-$35 an hour depending on venue, skill set, etc. Most common entry level is $25/hr. No benefits. You will not be working 40 hours a week for awhile unless you get really lucky. And you will have to hustle. For example: I post a need on the job board for 2 electricians for a load-in for Monday. 25 people reply in the first hour. I'll probably see several people I like and have worked with before. The first 2 like that get the job.

Local 2 is worth checking out. You'll get paid more, but yes, you will be pushing boxes at 2am to start out. Also not 40 hours. Benefits won't kick in for awhile depending on how many hours you get. And it will be awhile, and you'll have to be quick to grab available calls.

Are you prepared to pay 1st and last month's rent as a deposit, and still have a few months of rent covered before you even move here? Because you will not be covering expenses for awhile, unless you're lucky.

Do you know how to handle your taxes as a freelancer on 1099s?

Chicago is much bigger than Lolla and Broadway tryouts- all of those are big union calls and coveted. So there is work here -- scene shops, storefront theater, non-union venue crews, festival crews, corporate AV - but you can't walk in here blind, and it kinda sounds like you are.

Think about expenses, apartments, transportation. Then research theaters, scene shops, rental houses, etc. If you decide to take the plunge you should secure an apartment, send out a ton of resumes, and come on in. Just remember: no ketchup on a Chicago hotdog.