+1 for Iwan Ries
IMO, the best Italian in Chicago.----
http://www.italianvillage-chicago.com/
The have a great wine list to say the least. There are 3 restaurants that make up the Italian Village, all in the same building, go to the original Village which is upstairs. Here is more of a visual-
http://www.italianvillage-chicago.com/video.php
Capital Grille has great steaks. I think they are on N. St. Clair, just off Michigan ave.