Since when is N.C. considered up north? Same deal here hot humid summers. Winter is cold but not near as busy as the summer months. Your never gonna find a perfect climate if you do you'll be out of a job.
If you want to stay a wus, stay down there. If you want to walk off a roof at 3am having saved the world, in 20 below weather, snowing, and be a REAL MAN, then yeagh it's better.
Good luck on your job search, but just so you know, Chicago is a bit chilly.
The Chicago roofing contractor business is an interesting one. I wish you the best of luck!