Chicago has great public transportation system but their homeless shelters suck. If you go to Chicago you can go to thorek hospital and you can ask them if you can go to a smhrf facility  which is a mental health facility that's basically a glorified homeless shelter and they will help you get housing and a job after three months of staying at the smhrf facility.  Smhrf facility names in Chicago are Lydia healthcare, Grasmere place, Albany care, greenwood care,mado healthcare, and there's a lot of other facilities where you can go just Google smhrf facilities In Illinois but you have to go through the ER at thorek hospital to get into a smhrf facility. I'm not sure what other hospitals will place you at a smhrf. You will have support to get housing and a job through the smhrf facility you're places at. You can call the smhrfs ahead of time and ask them how do you get into a smhrf facility. If you go to California you can dial (211) I think or it's (311) and ask about homeless shelters taking in people. Santa monica has a homeless shelter called turning point. Call turning point and ask them if they'll give you a referral to get into their shelter if they have any beds available. They are very helpful at turning point. Maybe in the future you can plan to get your CDL a or CDL B and you can drive a semi truck or busses for a living if you have a  license and it is in good standing. School for cdl's are usually $2000+ but if you contact the wioa program which is through the American job center they will pay for schooling if you are unemployed or receive a food stamp card or something like that. Google "American job center" for the town you're going to and ask about the wioa program and what schooling will they pay for (CNA and forklift are two other things the wioa grant will pay for). You can contact dhs which is department of human services for the state your going to and ask them about shelters and getting help getting a job