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While Chicago and New York are tops (in that order) in Industrial and Post-Industrial Era architecture and skyscrapers, Philadelphia is like a textbook of ALL architectural styles because of it's rich history: Colonial, Georgian, Federal, Greek Revival, Victorian, etc.
Philadelphia after all was home to some of North America's greatest architects, including Samuel Sloan, Frank Furness, Horace Trumbauer, Paul Philippe Cret, and Louis I. Kahn. Even outside masters like Frank Lloyd Wright and Cesar Pelli created some of their most important works here.
I'm embarrassed as an architect that I haven't been to Chicago as an adult so I can't speak from personal experience (hopefully that will change this year) but of course you would have to be living under a rock not to have that city about as high as any other.
I haven't been to Philadelphia since I was a kid but even now I can remember its amazing cobbled streets and overall great architecture.
NYC has some standouts but it also has a lot of bland density; that's somewhat true of just about all cities though, same with Boston- love Back Bay, Beacon Hill and North End (but how much red brick, cheap builder Capes and three deckers can one person take as you get out in the burbs?)
My favorites, especially when it comes to both domestic and commercial architecture are St. Louis, Pittsburgh and San Francisco.
Portsmouth for its scale and Alexandria for its pristine blocks of Georgian perfection.
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