The Chicago city schools require that teachers live within city limits. That may or may not be important, but it can limit flexibility.
I love Lake Michigan. Was not a huge fan of Hyde Park when I lived there, but loved the walk to the Point.
You are rocking it out with the teaching advice and it's really helping me feel less anxious. Our goal is definitely to live within the city proper. I'm almost starting to get excited about something that may happen sort of soon.