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shesus did a great job of hitting most of the high points. There are a few others, though.
The Signature Room has mediocre steaks but great views from the top of the Hancock Building. But they also have a bar. Go get a drink there. It's worth paying for an $8 beer, which is only $0.75 less than Wrigley.
Cubs tickets can be impossible to find if the right team is in town. If the White Sox or Cardinals are playing the Cubs, forget paying anything under $100. But if it's the Dodgers or Mets (for instance), you'll probably find something reasonable.
There are HUNDREDS of great bars and restaurants. Rather than flooding you with names, give me an idea of what you want.
There are several architectural tours, which kind of sounds boring until you realize how many buildings are unique to the city and what architecture does for the place. The boat tour is good, but you should also take a walking tour. You'll see and learn more. The Chicago Architectural Society is the one that you want to on, not any of the others. The others have hosts that rarely know what they're talking about and often are absolutely wrong about the facts.
See the Science and Industry Museum if only for the only captured German U-Boat.
There are some cemetery tours that are pretty neat as well.
That's what I can come up with off the top of my head.
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"We have met the enemy and he is us." - Pogo
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