I haven't gone through your situation. I've gone through bad depressive episodes where I became very nearly unable to live on my own.

Coming out of one of those feels like convalescing after a serious illness (I suppose that's what it is.)

I'd say that the biggest thing in favor of your being able to live on your own again is that you did it successfully before. You have history there and lots of skills.

You'll have to decide when you're ready, or close as you think you're going to get, and then go for it.

Another alternative would be to stay in the town where your parents are but get your own place. Or you could do that first and then decide whether you feel ready to move back to Chicago.

Best of luck to you.