John,
So far, MikeS3 has made the best combo selections for you (dinner & dancing). I would also add Nacional 27. Nacional 27 is a Latin influneced restaurant that has live music after 9, I think. Also, Jilly's Piano Bar; 1007 N. Rush St.; 312-664-1001.
As far as restaurants, some of these are pricey:
There's always the standard...
Signature Room at the 95th
875 N Michigan Ave Ste 1525
(312) 787-9596
Everest
440 South LaSalle St
(312) 663-8920
Geja's Cafe
340 W Armitage Ave
(773) 281-9101
Italian Village
71 W Monroe St
(312) 332-7005
Ambria
2300 N Lincoln Park W
(773) 472-5959
After dinner (Jazz/Swing type mood):
The Green Mill
4802 N. Broadway
773-878-5552
Andy's Jazz Club
11 E. Hubbard St.
312-642-6805
Davenport's Piano Bar and Cabaret
1383 N. Milwaukee Ave.
773-278-1830
I hope this helps. If not, the search will continue.
Francisco