Toronto has officially hit 100 skyscrapers according to CTBUH's numbers. (Reddit post is mine below)
Toronto's metro will surpass Chicago's in skyscrapers when every skyscraper under construction is complete, which would likely be around 2027-2028. Toronto proper will surpass Chicago not long after, around 2030-2032 (by my estimation). If Chicago never gets a massive construction boom again, it will be permanently left behind.
Chicago is still some ways ahead in the supertall department. However Toronto has 3 U/C and 1 likely to be built (Forma), so it will reach half of Chicago's 7 by 2030. Considering the number of supertall proposals, it will likely surpass Chicago in this regard eventually as well.
https://www.reddit.com/r/skyscrapers...ers_making_it/