Chicago and Toronto might share some high-level, lake city elements, but Montreal seems more like Chicago on the street level to me.
https://www.google.com/maps/@45.5232...7i13312!8i6656
https://www.google.com/maps/@45.5218...7i16384!8i8192
https://www.google.com/maps/@45.4763...7i16384!8i8192
https://www.google.com/maps/@45.4783...!7i3328!8i1664
https://www.google.com/maps/@45.5156...7i16384!8i8192
Montreal has a tighter scale and narrower streets, and Chicago has that midwestern gigantism, but I've always seen a similarity in scale and typology there.