I found an article asking why they exist and confirming my primary theory. When Daniel Burnham planned the city, his primary design placed streets on a grid system. However, his plan also called for diagonal streets to accelerate ingress into the city center from the outer neighborhoods.
Prior to reading the article, the diagonal streets inspired a small blurb of poetry in my mind - "These streets, strange to the rest of the city, are the key to its heart. Rushing ever faster the closer we come." After reading the article, the blurb has lost a bit of its luster, though.
It turns out only one of the streets, Ogden Avenue, was a part of the planned vision. The source of the article, Chicagoist, added a bit of its own leftist snark in its quote that the diagonal streets "as always, [are] all about buying stuff." This opinion appears to be predicated on the impression that people only head toward a city center to shop, or simply support capitalism via working or dining or spending money or erecting statues to Adam Smith. I guess from a deconstructionist point of view, this may be true, though it's a pretty cynical and reductionist interpretation. Rather than engage in some early college-style light debate about the evils of capitalism and cities' roles in propagating that evil, I'll just be happy with my initial poetic thought about moving toward the city center.
However, the line does lose its luster again when discussing America's second favorite past time to capitalism - expelling native Americans from their homeland. As with Ridge and Rogers, the diagonal streets don't come from an architect planned expansion but rather from old Indian trails. Milwaukee Ave. was actually a buffalo transit route to the Chicago River. American settlers commandeered the routes and established their own lives along the trail (and, in a nod to capitalism, set up toll roads along trails).
A side note - Chicagoist, a blogging site where I used to consume most of my news about the city, is no longer in service. It was abruptly shutdown by its owner when its employees attempted to unionize for better working conditions. Maybe their leftist snark wasn't so misplaced after all.
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