Guys thanks for all the feedback and replies, you've all been a great help.
My buddy said it best "Chicago is the Miami of the north" Which in many senses is true.
I actually like Chicago quite a lot. Not too fond of winters these days though, but oh well.
I do have a bike and may quite possibly be purchasing a second one and maybe I'll just have one stay in Florida and commute there to visit as one of you guys were saying.
I feel like there might be more to do in the Chi than in Dallas but who knows...