Ha, lovely, you are the city...nice idea, I wish I could say the same for teh realization. In fact, I quite like the colours of the city and the street, but not from your room.
I copied this image, and turned into b&w, it looked better because of the grains. Unique idea, I am not sure about the second person in the picture, but I think it gives a "ordinary day" feeling. Good photo overall :)
I really like where you're headed with this, so this is the only reason i feel compelled to leave an extended comment.
I feel like some technical shortcomings detract from the image. For one, looks really noisy/grainy, as though the image was underexposed and you tried to brighten it up in photoshop, but that inevitably results in a lesser quality image. Or maybe you were just using a hight ISO. In any case you could have remedied this (to an extent) by smoothing the picture with noise-reducing software like neat image. Also, I think you could have bumped the contrast a bit, the dynamic range of the photograph seems relatively limited -this could have been augmented through some levels or curves work. Finally, dodging and burning are your friends! Some subtle selective brightening of your (for example), could really have a drastic effect on the overall feel of the photograph, play around with it!
I especially like the person sitting in the background of the reflection with their back turned to you, i think that adds an added element of depth both physically and emotionally and brings the image to a new level. Oh and Chicago is a great city, i was just there visiting a friend. Sorry for the long read and good luck!
I really like your idea, but fear that you won't get that high of a score because the main subject is you, not the buildings and street, and you have to sort of look hard to see real definition in your features and SP. It is a really great idea, but more of you would have been better.
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