I know another first timer that is after all kinds of info. All I can say is I would help you if you were coming to Toronto!
We are staying staying at the Palmer house.
We are open to anything (Great BBQ, Seafood, Steak, Pizza, Ice cream)
If you are in Chicago and budget is an issue but not a big issue. Just cannot go crazy.
Based on that...
What steakhouse would you suggest and Pizza place that gives us a real taste of Chicago?