Chicago is heaven. I lived in the area for 7 years and loved every minute of it, and yes, even when there were snow showers 32 inches deep and there were "flesh freeze warnings" issued. If you're from LA, you're in for a shock in weather. However, the summers are very pleasant. As far as flying goes, I did all mine at VPZ porter county municipal in Indiana, about an hour train ride from downtown at Donnair flying warriors and a baron. At VPZ, there is also Eagle aviation, which flies cessna 172's. They are a cessna pilot place and have Sallie Mae financing available last I heard. The facilities are great and you're cross countries take you to Midway (C), Kalamazoo (TRSA), Gary (D) and South Bend (C). This is the only first hand stuff I have but I've hear really good things about the guys at Romeoville, IL at Lewis University. The CFI guys run training out of there even if you aren't a student at Lewis and it's just south of the city. Hope that helps.