Oh man, that is dumb. I hear Chelsea is just like White Plains except on the island. Like one of my friends in the neighborhood has a car and no one lives in a house 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?