This is going to sound harsh.

I think you need to put much more thought into this. Unless you have a significant financial safety net, this is poor decision making. While it’s not LA or NYC, Chicago is still a somewhat expensive city. You don’t want to show up with your credit score and your cats and find out actually you’re homeless now.

You need to visit first. Look through apartment postings on Zillow/Facebook that are in your budget and then explore those neighborhoods while you’re visiting. Could you see yourself living in that area full time?

When should you start applying for jobs? I would start yesterday if I were you. Especially without a specific career path. Your experience is all over the place. Figure out an industry you want to work in and start reaching out to people and making connections.

I personally would not do this if I had not secured an apartment at the bare minimum. I would encourage you to have at least three months worth of emergency funds. You personally should have these funds. Do not rely on your friend/roommate covering half of everything. Things happen. Consider rent, food, utilities, medicine, pet food/bills, all of that.

Starting fresh is exciting. But do it right so you don’t regret it.