Chicago confirmed for me that the ambiance and aesthetics of cities do correlate to size. The height and density of Chicago's River North neighborhood demonstrated, for me, the allure of Seattle's continued infill development.
What Chicago seems to lack is the density of subcultural elements that makes Seattle greater than it might look "on paper". Although there are neighborhoods that have a cool vibe to them (e.g. Wicker Park), the culture en masse feels less interesting.
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