Being in Milwaukee this weekend made me acutely aware of some of the differences between it and Chicago. It's more than just a matter of scale. The difference of size causes different attitudes, different mentalities.
Milwaukee is a city that's still close to the land. It is shaped by topography, sitting atop 80-foot high bluffs that overlook Lake Michigan. It's a small city, small enough that people who essentially live out in the country can take part in its daily life, and people who live in the city have many options for outdoor sports and activities. That connection gives it an often rural attitude. People in Milwaukee come from small towns. They root for the Packers -- it's not just a cliche. They hike and fish and hunt and backpack and camp and canoe on their weekends. That same rural attitude, applied to city living, gives the city an air of smart environmentalism; it also means that Milwaukee sometimes fights against its own nature as a city (just look at the hew and cry over bus funding and rail transit, or the reluctance to convert 794 to a surface parkway, or the fuss over tearing down a useless stretch of highway, or...) Milwaukee is a small niche of the (reluctantly) man-made perched among the vast wilderness of Lake Michigan.
Chicago by contrast has long since conquered nature, which is sequestered away in distant woodlands known collectively as the Forest Preserve. Chicago's Lake Michigan coast is entirely artificial, constructed over a hundred years of city-building, and gives an illusion of control over the vast body of water. The city sprawls for thirty miles in every direction, ensuring no easy escape from its artificial environment. The resources of the Great Lakes funnel down to Chicago, which is the drain through which they flow, the sieve that sorts them, the mill which grinds them up and churns out product. Chicago is less a part of Lake Michigan and more an engine strapped to its side, converting its resources to commercial goods and fountaining wealth across the region.
At their cores, the cities may seem similar -- glistening downtowns perched on idyllic lakefronts (indeed, Milwaukee's lakefront is no less artificial than that of Chicago.) But the difference is in how they spread themselves across the land. In barely five minutes of driving north from downtown, Milwaukee's Gold Coast high rises give way to single family homes, and five minutes after that these houses gain their own private beaches and forests. By Whitefish Bay, the view up the coast is essentially the same as it will be for the next hundred miles. One must travel a good ten miles north of central Chicago to find a single-family home with a lake view. Milwaukee is a short interruption of nature; Chicago is its own nature.