My wife and I very much enjoyed Everest on our anniversary. The food is outstanding (French/Alsatian), and the views are incredible (its located on the 40th floor of the stock exchange).
Everest
440 S. LaSalle St.
40th Floor
Chicago, IL 60605
(312) 663-8920
http://www.everestrestaurant.com/index.htm
As for Italian, I haven't tried too many of the favorites in town, but Spiaggia is a great Italian restaurant for a special occaisson:
Spiaggia
980 N Michigan Ave #2
Chicago, IL 60611
(312) 280-3300