For residential, Toronto's inner-city has a lot of sorta British-looking modest homes, now obviously gentrified, and often random garden apartments. Messy and vibrant:
https://www.google.com/maps/@43.6484...7i16384!8i8192
Chicago's residential inner city looks much more prosperous, substantial and orderly:
https://www.google.com/maps/@41.9364...7i16384!8i8192