> Most of the streetscapes that jump to mind about Chicago, if you don't live here, are places people basically don't live.

Note that 41k live in the Loop and 27k live in Jefferson Park.

Maybe if you sample by area, places look more suburban than stereotypical cities, but by population, lots of people live in the dense parts.

100k in the Near North Side, which I think is basically a “downtown” streetscape.

And of course many in the in-between density neighborhoods (eg 71k in Logan Square).

Source:

https://en.m.wikipedia.org/wiki/Community_areas_in_Chicago