Blessed with some of the best architecture in the country, Chicago's downtown area is a popular destination for design enthusiasts and urban sightseers. The ultimate Windy City panorama can be experienced at the top of the John Hancock Center. The 95th floor observatory offers a 365-degree view of the heart of Chicago. If you don't mind swinging for expensive drinks (or an even more expensive meal) the Signature Room, above the Observatory, is a great place for some after-dark skyline-viewing.
The famous Navy Pier, on the shore of Lake Michigan, offers some wonderful lake-level views, as does the less-crowded Montrose Point, a natural Uptown area that is also popular with birders. If you want a little bit of a rush, you can head to Navy Pier's Aero Balloon Rides. The balloons stay tethered to the ground, but rise to more over 300 feet above lake level, providing outstanding views of the city.