Something unexpected but for the first time in years I believe... an American city is tied with NYC for the amount of skyscrapers U/C!
Miami and NYC have 14 U/C.
But yeah like BrickellBased mentioned Miami needs a lot of U/C like Toronto, at least 30 U/C per construction cycle to overtake Chicago imo. But really numbers shouldn't be a goal, Miami should have extensive rail like Chicago and aim to build around those rail corridors with dense housing.
Also this doesn't consider if Chicago has another building boom, which it most likely will.. well because it's Chicago!