I know you, I recognize your username. You wrote the tool for OSX: phoenix, hydra, mjolinr, etc. I think you are a very talented developer. I think you'll definitely be able to get a job in Chicago easily. There is no shortage of tech jobs.
If it is too much stress for you to work as a freelancer, just get a full time job. There is no shame in that!
If it is too much stress for you to work as a freelancer, just get a full time job. There is no shame in that!