As a guy who has lived in quite a few large to world-class cities (Chicago, Tampa, Milwaukee, Atlanta, and Orlando), let me say this:
Don't live in Tampa or Orlando. Florida is a transient state and everyone seems to have a plan to stay for a couple years and get out. It's for a reason.
Atlanta is just ok. You can probably find arguments for and against its logistics, job growth, women, etc--personally I'd stay away.
Milwaukee is a great and growing a lot, although the weather sucks.
Chicago, well…you should stay there. Winters are rough, but otherwise Chicago is amazing. You can find something cheaper in Lincoln Square, Pilsen, etc for less than $1k for a 1 BR. I don't have to mention the quality of women, its international stature, public transit, etc. Stay where you are and just adjust what you're doing.