The Cubs win?

Chicago has great architecture--and often, great examples of different architectural periods on the same block (especially downtown). The Chicago Architecture Foundation gives well-reviewed walking tours, as well as the boat tour on the Chicago River mentioned by an earlier poster. More information is here:

http://www.architecture.org/tours.aspx

For what it's worth, one can buy tour tickets online, but for the walking tours, I just went to their store and exhibit space on Michigan Avenue and got them the day of the tour, saving the ticketmaster fee. The middle of summer might be more hectic, including for the boat tour, but you might just call and see what's up. A great way to learn a bit about Chicago in just an hour or two, from a typically very well-informed docent.

Also, there are many books set in or about Chicago. Recently, "Devil in the White City," about the Columbian Exposition of 1892-3, was a hot seller in Chicago and elsewhere. Many of Chicago's leading lights were involved in it, and reading it before your trip might spark your memory as you see their names elsewhere in the City during the trip.

-Hayden

P.S. Go Cubbies!