It has been a while since I was downtown, but there is a jazz club called "The Bulls" which was awesome. It is near Clark and Armitage in the Lincoln park area and its still around. Here's a link:
Spiaggia (fine dining) is in the top ten best restaurants in Chicago
1984-present // Gold Coast
(Italian) In a city with a proud red-sauce tradition, Tony Mantuano singlehandedly awakened us to the exquisite joys of Northern Italian cuisine.
My favorite italian restaurant is:
authentic Italian restaurants in the area just 15 minutes southwest of the Loop, Il Vicinato is the place to go if you like to eat till you explode.