If you want to be up high, hit the bar at the Signature Room in the Hancock. The drinks are overpriced, but the view is spectacular and at least you're getting a drink instead of paying just to ride the elevator. Oh, and my wife says to visit the ladies room, it has windows (none in the mens
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Take in a show at the Chicago Shakespeare Theater at Navy Pier..great shows and the best views from a Ladies' Room you will ever see (my husband claims Men's room view is equally awesome).
(I am told, I have not confirmed) the best priced Hamilton tickets in the country. Went recently on a Tuesday night for $125 per person in great Orchestra seats.