Why is it that you're primarily advertising attractions, tours, hotels and other 'tourist-y' information then?

Kinda doesn't make sense.

Methinks you should really reassess why you want this website up, and who it's for. This will help you focus on what you need to do to get where you want to be.

Design-wise, i think you need to work harder at finding out what it is about Chicago you love, and adopt that into some sort of theme for the site. Right now, it looks pretty plain and boring, and doesn't do much to drum up any excitement.

Hope that helps.