While Toronto now has more people than Chicago, the GTA is still less populated than the Chicagoland Area. Toronto has yet to have a building with at least 100 floors like Chicago, NYC & Melbourne.
There is always a strong resistance to allow the Greater Vancouver Region to rival that of Greater Montreal or the Greater Seattle Area. Thus, the trains are shorter, most of the bridges are narrower & most of the buildings are like stumps. The keep it small & hold it back approach, is all part of the symbolism towards refusing to build proper big city size infrastructure.