But Chelsea is the densest part of downtown and White Plains is quite a few suburbs separated from the city. If you live in like, Riverdale (Bronx) or Yonkers, it's pretty much the same thing. NY has actual physical boundaries that makes for an actual delineation. Outside the densest part of Chicago, there is no delineation. Manhattan is Manhattan. Take any part of the outer boroughs, sans Staten Island, and they butt up against some suburb that is essentially the same as the borough itself. What vast areas of Chicago proper would you characterize as spread out houses? I'd argue direct north of downtown is hardly like that until you get to Evanston (sans Ravenswood), same largely goes for the west side until Oak Park. The south side certainly would have more spread out houses, think Hyde Park and Brideport, but otherwise I'm having a hard time where you would be thinking....northwest? Generally speaking, stuff like the Irving Park and Bucktown areas. I only lived in the city for a few summers, and was in an apartment, as were most of my friends that stayed there post-college. But when I go back now and see friends/family, almost all of them actually in Chicago live in individual structure homes, separated from the house next door. On the urban - suburban - rural scale, these places are indistinguishable from many technically suburban places I have been. The suburb I grew up in was very much a suburb and not chicago. I couldn't get away with saying I grew up in Chicago. And on that note, I also no longer say I'm from the Chicago area, as I've officially lived more than half my life in NJ and have succumbed to answering the, "where are you from" question with a simple, "New Jersey".