Its tough to compare the two areas from an architectural standpoint. In Chicago you have MacDonald, Raynor, Colt, Allison, Ross, Langford & Moreau, Willie Park, Watson, Tillie, Bendelow, Tweedie, O'Neil, Leslie, Macomber, Dearie, Roseman, Diddel, Maddox, Foulis, Collis and even some Flynn. Philly has many of the same names as well as quite a few other major players that did some of their best work (if not their only work) in the area.
Both cities prospered during the Industrial age, resulting in the expansion of their suburbs and the eventual upswing in the number of golf courses built. In turn, both cities suffered tremendously from the 50's through the 80's as the plants, mills and centers of industry died out, with Chicago having rebounded a bit quicker into a "newer" city. Both cities have a tremendous amount of history, with Philly having held on to its revolutionary roots and Chicago highlighting the ideas of progress and innovation.
There is no better city in the country during the summer than Chicago. While Philly, NYC, DC and Boston empty out on the weekends, Chicago draws people in. The locals don't flood out of town for the Shore, as its a beach town, a sports town, a center of culture, a bar town and a golf mecca all wrapped into one. I lived in Philly for a number of years during the 90's, and even Manayunk felt dead on a summer weekend.
I will give the nod to the cheesesteak over any of Chicago's signature food items. And there is no greater expert on this forum on the state of the US brewery market than Bill Seitz.