Last weekend, for the first time since leaving the Midwest in 2002, I spent time enjoying Chicago. The best part was visiting my daughter, but the second best part was seeing Millennium Park, the New Modern Wing of the Art Institute, and just plain walking around and eating in Chicago.
Within one-half mile of Lake Michigan, from Cermak Road on the South to the Evanston city limit on the North, Chicago is an Urbanist's dream. It is walkable, it has more impressive urban landscapes than any other city I know, transit is good, there is well-tended and contiguous green space, and, of course, the magnificent lakefront.
So why don't we have more Chicagos? Part of the reason is that countries have systems of cities, whose size seems to kind-of-sort-of follow Zipf's law, and so there is room for a limited number of cities of Chicago's size. But one could ask why we don't see Chicago in miniature more often. To the extent that it is preferences--that there are only a limited number of us who like the features of places like Chicago--the fact that there are few Chicagos is nothing to worry about.
But I suspect that it has to do more with policies--zoning that requires separation of uses, low densities, large setbacks, etc. Particularly problematic is the hostility many communities show toward multi-family housing, and the silliness of greenspace requirements that encourages many little playgrounds but fails to develop large parks. The again, policies are put into place by elected officials, so maybe the absence of Chicagos does reflect preferences (or prejudices). And that's too bad.
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