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Sufjan Stevens – Chicago Lyrics 12 years ago
I think this song is about the human experience of the search for satisfaction and maturity.
The song starts off "I fell in love again".
This is an extremely common human experience. We find ourselves suddenly in love with someone or something. Perhaps even and idea. Like driving to New York or Chicago to have new and exciting experiences.
But the only down side to this human experience is that we usually only are in love with something in our mind and find ourselves moving on, unsatisfied.

I think the really important thing to notice is the conversation in the song.
Part of the song is about seeking satisfaction and understanding. But in between these lines is the realization that all these things go to recreate us and make us grow.
He repeats "I made a lot of mistakes" many times because that is just how we as humans feel. We make mistakes.
But we can be reassured that these mistakes and ideas only to go to refine us and recreate us.
Essentially, life is a series of realizations of how stupid you were five minutes ago. But it's all part of God's plan to cultivate and grow us and eventually bring us to himself.

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