I really, really apologize in advance for what I'm about to do, but here it goes anyway.

I'm a fan of a band based out of Chicago. Their fan forum has an absolutely phenomenal post/thread about what to do in Chicago, written by some long term residents and Chicagophiles.

I don't know if you will be able to read it without registering, but here is the link to the thread.

FWIW, I get to Chicago at least once a year, and my visit is not complete (and I've completed quite a few visits over the past decade) without a stop at Lou Malnati's for deep dish. That is sure to raise the hackles of some of the locals (I know, Gino's), but to each their own