The actual title of this song is not 'Image Of Chicago' but the much longer ‘Kevin and Brendan Paint an Image of Chicago w/ Casual Women’ is. Here is the story behind it:
Sam Cowan (aka. Casual Woman) created the song that Caleb Groh (who, back in the day, used to go by the moniker 'Happiest Lion') couldn’t stop listening to. He asked Sam if he could write words and sing on it. Sam said yes. And then Jack Sjögren put together the video.
The track used to be able to be found on Happiest Lion's album Homemade, but over time, that album has seemed to vanish off the internet.
Luckily this video hasn't.