Grew up in Chicago. Have been in Florida for 10 years. Well kind of, we live in Miami. Whenever I spend time in other parts of Florida, like we did last weekend, it's a constant reminder that there is Florida and there is Miami, Florida. Totally difference vibe, totally different feel to it.
When we first decided that we were going to look for something outside of Atlanta, where we lived for 15 years, we eliminated Florida as an option for a variety of different reasons. We justified our move to Miami by coming to the conclusion that it's not like the rest of Florida so we weren't really moving to Florida. 
We like it here but I definitely would like to be able to get back to the Midwest at some point. Maybe just for the summers though. Summers in Florida can be brutal but I have gotten used to the humidity. Doesn't mean I like it anymore but you can't beat October through May down here when weather everywhere else sucks.