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Chicago is a little bit pricey because its such a major hub. You might want to try a smaller city in the midwest like Cleveland, Ohio. We live outside of cleveland and compared to where we used to live in the DC suburbs, its EXTREMELY cheap here. Some friends of ours just bought a nice house in a nice neighborhood for 110,000 dollars, to give you an idea. It wasn’t a huge brand new house, but like I said in good shape if a bit old in a good neighborhood with a good school system. And cleveland has lots of educational opportunities – the community colleges are great, and there is a private university in Berea (a suburb) called Baldwin Wallace College that has programs for moms seeking their degree. Other universities have similar programs, you just have to check around and do some emailing. There’s Kent state, Cleveland state, Akron U (wouldn’t live in downtown akron though), Case Western (very pricey but there’s lots of scholarships available), and the community college (cuyahoga community college) is exceptional as well and the credits transfer well to other schools.
Also, your parish priest may be able to get into contact with parish priests wherever you’re looking to relocate to and they can organize some help for you while you get on your feet.
I hope that helps a little. As far as your decision, just pray about it. Maybe a novena. EWTN has a great list of novenas: http://www.ewtn.com/Devotionals/prayers/novena.htm
Good luck and God bless!