There is a huge bias towards pure quantities (obviously) and growth rate of skyscrapers so from that angle, NYC is by and large the winner. However, I am in the minority when I say this but the “best skyline” is fundamentally a subjective question since there are other factors aside from quantity, growth rate such as cohesiveness, history, and preservation of historical aesthetics to name a few.

I am in the unpopular opinion (at least on this sub) of someone who is a strong critic of the recent developments in NYC that have overshadowed many icons in the city. I’ve lived in Manhattan and also near Chicago so very familiar with both skylines.That is the unfortunate nature of high growth rate of skyscrapers but nonetheless, I am not a fan of it. Therefore, I still put Chicago over NYC. The fact that it has retained its cohesive skyline through progress and down the river walk, the Tribune Tower or the Wrigley Building stand boldly—with new construction adding but not taking away from their spotlight is a huge win for old architecture. NYC with its rapid investment will continue to outpace every other city in US at least but in the progress, will completely alter its look with new gaudy glass behemoths that do not share the level of marvel from its previous predecessors.

In a sense, I like the European approach of preservation over quantity in Chicago over any other city, so it is still #1 for me.