Chicago is great, can def vouch for it. It's definitely still expensive here though and rents are absolutely SKYROCKETING right now.
I'd say getting in with a unionized trade is a great option. At least in Chicago that could be nearly anything that you'd think of (plumbing, electrical, welding, etc) or things maybe you aren't thinking of like parks, streets, janitorial, etc if you've got a body that can do those sorts of jobs. Or look into apprentice programs for things like building inspectors, code enforcement, etc. There's lots of jobs people can do that can really be a genuine career if you can get yourself into an apprentice program for it. Basically every city job and trade job in Chicago is unionized and the unions are pretty strong.
Is there something that you want to do?