^ Ooh interesting question! That photo really is incredible. It'd be so cool if that sort of granular low-height ultra-density was still as prevalent here. It's worth noting that the photographic method (ultra-high-focal-length lens, taken from an aircraft) is making it look even denser and compact than it actually was.
I'm not sure I'd prefer living in the city back then-- the average building was more beautiful, and the urban fabric was better-stitched, but it's also devoid of trees and sidewalk amenities, there's huge industrial facilities taking up all the river space, etc. Michigan Ave looks like a miserable place to be hahaha.
Also, every building was a coal-smoke-belching nightmare. The photo's colorization might not accurately portray the amount of black soot that caked the city back then. Here's a pic from the Driehaus Museum of what it looked like before being cleaned:
Granted, that's after more elapsed time. But yeah, there's a happy middle ground that eludes us. I'm glad we still have some stretches on Hubbard and Clark that maintained and modernized their historic buildings, I'm glad the factory lofts on Franklin are getting converted to housing, and I'm glad the damn parking lots are slowly getting infilled
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