I say go to mike dika's resturant on chestnut st, just off Michigan ave.
order the spicy sliders for appetizer, a cup of the crab bisque, the blackened prime-rib for an

entree', and the chocolate moose pie or banana cream pie for dessert. oh theres a good chance that you meet Mike Dika himself, when your there. You want entertainment go there Friday or Saturday night, and Mr. John Vincent, will be there singing the tunes of Frank Sinatra,

Dino Crochetti(a.k.a. Dean Martin), and some others.
For a Late night seen stop Over at "The Red Head Piano Bar", Another great place , espeaicaly if you want to hang with some of the celebrity's.
For good Deep Dish Pizza, Order a Lou Malnati's, or go downtown to Uno's or Due's.
If you have any questions just ask.