Chicago's Elevated Train
The Chicago Transit Authority’s elevated train network, known colloquially as the “L,” seems like it was almost tailor-made for sightseeing. Of course, not every neighborhood in the Windy City is worth a visit, but the central Loop area, served by multiple lines, has some great track-level sightseeing. In fact, the Chicago Architecture Foundation provides tours (they’re not free) on the L, both of the Loop's buildings and of the architecture of Chicago's South Side. However, for the price of a standard train ticket (a flat $2.25 fee regardless of distance), you can skim over the rooftops and in between the historic buildings of this storied city and enjoy its legendary architecture for yourself.