I like the Hilton on Michigan with a room over looking Lake Michigan and Buckingham Fountain. Its about in between The Magnificent Mile and Navy Pier (Shopping).
You gotta hit the Signature Room for dinner or Cocktails (95 Floor of the Hancock, like Copo mentioned) as well as the observation floor at the top of the Sears.
Museums are close by, Buddy Guys Blues Club is around the corner, if still open.
Food:
Best Steaks; Gene and Gorgetti's or Gibson's
Best Sea Food; Nick's Fish Market
Best Chicago Deep dish Pizza; Giordano's
Italian Food; Hit Taylor Street. No bad choice there.
Greek Food; The Greek Isles
Fondu; Geahas (sp?)
Best Choice of Cigars after hours; Tavern at Rush
Check out the play "Wicked", great for Family entertainment!
