Chicago...

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8. Take a Segway tour, cocktails at top of the Hancock

We did a great Seway tour years ago of the Lakefront/Grant Park and Museum Campus. It is great fun and you get a great overview of this gorgeous part of the city, and can cover so much ground. Just pick a place that keeps the groups small - those make sure you really know how to ride it before the tour heads out.

The view from Hancock observatory is fabulous, but you can opt instead of paying for observatory, go to the bar which is nearly as high up and still get the views.

Already mentioned above, but I will second that the Architectural River boat tours are great.