Okay, so here's my interpretation, and it is most likely based upon my own life experiences, as most interpretations are... butttt Chicago and New York are actually two seperate people. Chicago is the person that he just recently broke up with, the one that it's still so fresh that he's still trying to cope with it and he thinks he's close, but he just keeps fluctuating and everything reminds him of her.
The last part:
"The wind's feelin' real these days,
yeah and baby it hurts me some...
Never thought I'd feel so blue,
New York City you're almost gone.
I think that I've fallen out of love,
I think I've fallen out of love,
I think I've fallen out of love...with you"
Is talking about an old love, perhaps a first love (at least for me :) ). That person who you never thought you could get over, and probably even still thought about throughout the aforementioned love, the person who you always seem to compare everyone else to, and yet some how that person is almost gone from your memory. You're finally reaching that point where you can let go of that person, where you've fallen out of love with them and can feel the wind of others- but it's a melancholy feeling, because you got so used to missing them that now you're missing that loneliness that came from loving and missing them- it became a comfort zone, and now it's almost gone as your love for them has ceased.
Okay, so here's my interpretation, and it is most likely based upon my own life experiences, as most interpretations are... butttt Chicago and New York are actually two seperate people. Chicago is the person that he just recently broke up with, the one that it's still so fresh that he's still trying to cope with it and he thinks he's close, but he just keeps fluctuating and everything reminds him of her.
The last part:
"The wind's feelin' real these days, yeah and baby it hurts me some... Never thought I'd feel so blue, New York City you're almost gone.
I think that I've fallen out of love, I think I've fallen out of love, I think I've fallen out of love...with you"
Is talking about an old love, perhaps a first love (at least for me :) ). That person who you never thought you could get over, and probably even still thought about throughout the aforementioned love, the person who you always seem to compare everyone else to, and yet some how that person is almost gone from your memory. You're finally reaching that point where you can let go of that person, where you've fallen out of love with them and can feel the wind of others- but it's a melancholy feeling, because you got so used to missing them that now you're missing that loneliness that came from loving and missing them- it became a comfort zone, and now it's almost gone as your love for them has ceased.