Chicago was magical for me... but I guess since I was only there for a week, I might not have gotten the full experience. And we kind of mainly stayed in the Michigan Mile region for the majority of the trip. We did drive to Skokie... but that was for a reason I'd rather not get into.
Austin is really great... if you've got the time and resources to go downtown to 6th street and really enjoy the nightlife. If you're under 21, the bars and clubs usually dont welcome you with open arms, a stark contrast to where I'm from... which is hardly Caribbean, Chillster. It's South Padre Island... Spring Break is a MESS.