Friday Five :: Songs about Chicago

1Songs About Chicago


For the month of September I will be picking a city to do a Top 5 Songs of Post for the weekly Friday Five theme. The third installment is a city that is full of mixed feelings and bittersweet memories for me, a city that I tried and failed to live in twice, a city where I fell out of love and in love, made some significant mistakes, had incredible times with friends, and grew incredibly attached to the trains and one little dive bar with the best jukebox I’ve ever encountered. I will get back there someday, not to live, but to visit, and create some new memories, too. A part of my heart will always reside in the city somewhere, blowing around in the wind, riding the Red Line, working late night shifts in a now defunct record store, dancing in a New Wave themed club, and taking turns picking songs on that damn fine jukebox with great friends.


… Chicago divided your heart. Leaving you loving the joint for keeps. Yet knowing it never can love you.” ~ Nelson Algren

Sometimes words are just music themselves. Like ‘Chicago’ is a very musical sounding name.” ~ Tom Waits

There seems to be a different Chicago around every street corner, behind every bar, and within every apartment, two-flat, cottage, or bungalow. City of immigrants or city of heartless plutocrats, say what you will, Chicago almost defies interpretation. In many ways Chicago is like a snake that sheds its skin every thirty years or so and puts on a new coat to conform to a new reality.” ~ Dominic A. Pacyga

Eventually, I think Chicago will be the most beautiful great city left in the world.” ~ Frank Lloyd Wright


Following are my Top 5 songs about the Chicago. Do you have any?

1. Chicago (acoustic) :: Sufjan Stevens

“I made a lot of mistakes.”

2. Dear Chicago :: Ryan Adams

“Sorry about the every kiss, 
every kiss you wasted bad.
I think the thing you said was true,
I’m going to die alone and sad.”

3. Via Chicago :: Wilco

“I painted my name on the back of a leaf,
and I watched it float away.
The hope I had in a notebook full of white, dry pages,
was all I tried to save.
But the wind blew me back via Chicago,
in the middle of the night,
and all without fight,
at the crush of veils and starlight.”

4. Hands Open :: Snow Patrol

Put Sufjan Stevens on,
and we’ll play your favorite song.
Chicago bursts to life,
and your sweet smile remembers

5. This City :: Patrick Stump featuring Lupe Fiasco

“You can take my picture,
you can take my name,
but you’re never gonna take my city away.”


6 thoughts on “Friday Five :: Songs about Chicago

  1. Though it’s a love song, a heartbreak song “Tonight, Tonight” qualifies as a Chicago song with the lyrical nod to the city as the setting. Seems some people got burned out on that song long ago, especially Billy Corgan,but I never did, it’s perfect.
    Otherwise I’m no help I can’t think of ONE Chicago song at the moment:/

      1. I think I always thought it was a love/break-up song but after I wrote that I was remembering that I heard it wasn’t about that but I can’t remember the deal so I must search the web on that one… at the least the Chicago reference is in there! Wonder what city you’ll do next… hmmm!

  2. Please do come back to visit. Chicago is my town & I may be a bit biased but it’s the best city anywhere. 😉
    Some songs I like are
    My Kind Of Town by Frank Sinatra (pretty obvious)
    Sweet Home Chicago by The Blues Brothers
    Jesus Just Left Chicago by ZZ Top
    Shy-Town by Gorillaz
    Great post!!!

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