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"Rental cars are not the favored method for visiting cities, especially those outside one's own country. Instead, tourists and urban planners favor packaged tours or local public transport systems. Both are splendid ways for seeing the city as it used to be -- the very reason for most tourist visits. The historical core areas contain monuments, prime government and religious edifices and quaint neighborhoods that are often centuries old. This is particularly important to tourists from the newer urban areas of the American, Canadian or Australian West, where history extends not far before World War II."
But sticking to historical cores can be misleading. "Both public transport and packaged tours miss the larger part -- the expanse of sprawling residential and business development that rings virtually all major urban areas. They may be of little interest to many urban planners, but they should be.
"Stripping away regional architectural facades, one might as well be in the suburbs of Phoenix, Portland, Perth or Paris. Here, the automobile is king, because no public transport system has been developed that can effectively serve destinations outside the core (at least at a price any society can afford)."
You can read Cox's take on Saint Louis (his home base), Detroit, Kansas City, Cincinnati, New York, Miami, and lots of cities outside the U.S. -- but not Chicago, yet. The index is here; the tours themselves are PDF. My sense so far is that Urbanophile's right to think Cox sees things of interest even to those who don't always follow his politics. (How long has it been since I was last able to write that sentence?)