To make it easiest on me, I would likely live very close to the downtown area. It would be expensive, but I'll make enough to afford it and I'd likely otherwise forfeit whatever is left of my sanity.
I actually was born, raised and lived in Chicago my whole life until about a dozen years ago. I prefer Phoenix all things considered. But I'm working on ways to mitigate the worst of Chicago (the soul crushing winters).
220.5 this morning.
Tried an interesting tactic last night. At the bar watching the baseball game, and the baseball game was such that I stayed much longer than I had anticipated. The end result was three more beers than I wanted. So when I left, I calculated how much exercise I had to do to burn off those extra 400 calories and then went back to the health club for the second time (it was about an hour and a half before close). 45 minutes and 33 seconds and average heart rate of 132 gives me a net burn of 542 calories. However the key will be how today progresses. You can't just exercise hours upon hours every day without your body giving in, at least not at 42 years old. My calves are a little tight right now, but so far so good.