If you go to Chicago, a definite must-do is the architectural boat tour, even if you are not an architecture buff (and I am not). It is a great way to get some history, get a special view of the city via the water, and find out some cool tidbits about the city. And, there is definite beauty in seeing the different eras of architecture. I also respect the innovation and creativity of the architects themselves, especially because this is a talent that I do not possess at all.
This tour also made me think about the connection between history, literature, and culture. I hadn't realized how architecture is also defined in the same terms as literature (like postmodern, contemporary, etc.), and I like thinking about American history in this way--it makes me feel connected to the past and our ancestors. It's inspirational to think that authors, architects, scholars, politicians, etc. from different eras were and are all connected and often on the same wavelength. Very cool.