A degree is way overrated. College isn't for everyone. I know to many ppl with degrees working at jobs they hate cause they hate what they got their degrees in. Its stupid to think that just cause you went to college that your educated, and you will get all these great jobs and your life will rule, its just not true. Anyone can make a living doing things that don't need degrees,and that they love, just don't be scared to work your ass off to earn it, because there's always gonna be some ****face with a degree who thinks hes better than you because he got a D in calculus, HA.
I would not vote for Chicago BTW. F' the F'ing weather in this god forsaken city. Go somewhere warm, not chi. Granted, Chi can be cool, and it would be the biggest city in the country if, and this is a HUGE if, the winter was at least tolerable. But as it stands the winters out here are so oppressive, its hard to quantify.
But yeah, go for it man. I would just take a road trip with your bike to like 5 cities you are interested in, then you might have a good idea of what you want from a city. I vote NYC, just do it, don't be a *****.