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20 Best Songs About Chicago

December 5, 2023
Songs About Chicago

I’ve curated a list of the best songs about Chicago, each capturing the essence of this vibrant city with its rich musical heritage and urban charm.

This article is a musical tour through the Windy City, exploring tracks that celebrate its unique character and history.

Top songs about Chicago

  • Frank Sinatra – “My Kind Of Town”
  • Sufjan Stevens – “Chicago”
  • Aretha Franklin – “Think”
  • Chicago – “Take Me Back To Chicago”
  • Ryan Adams – “Dear Chicago”
  • The Alan Parsons Project – “Sirius (Chicago Bulls Theme Song) “
  • Spoon – “Chicago At Night”
  • Buddy Guy – “Meet Me In Chicago”
  • The Blues Brothers – “Sweet Home Chicago”
  • Allister – “Somewhere on Fullerton”

1. Frank Sinatra – “My Kind Of Town”

“My Kind Of Town” is probably the most iconic song about Chicago.

It’s the combination of Sinatra’s timeless charm, feel-good melodies, and a mention of everything that makes Chicago such a great city.

“Each time I roam
Chicago is calling me home
Chicago is why I just grin like a clown
It’s my kind of town.”

2. Sufjan Stevens – “Chicago”

Sufjan Stevens wrote hands down one of the most beautiful songs about Chicago.

He released it on his 2005 studio album “Illinois.”

The song talks about leaving everything behind and starting again, and it feels very genuine, uplifting, and sentimental.

“I fell in love again
All things go, all things go
Drove to Chicago
All things know, all things know.”

3. Aretha Franklin – “Think”

Aretha Franklin didn’t grow up in Chicago, but she had many ties with the city.

In fact, she got the name “Queen of Soul” in Chicago.

She also appeared in the Chicago-based film “The Blues Brothers” where she performed her unforgettable hit “Think.”

“You better think (think)
Think about what you’re trying to do to me
Yeah, think (think, think)
Let your mind go, let yourself be free.”

4. Chicago – “Take Me Back To Chicago”

“Take Me Back To Chicago” is a dream of simpler times, a warm summer breeze, and familiar streets.

It’s one of the popular Chicago songs released in 1985 on the band’s compilation album of the same name.

“Take me back to Chicago
Lay my soul to rest
Where my life was free and easy
Remember me at my best.”

5. Ryan Adams – “Dear Chicago”

Ryan Adams’ “Dear Chicago” is a heartbreaking song about past loves and comforting cities.

It’s one of the songs that mention Chicago in a very sentimental way.

“Dear Chicago,
You’ll never guess
You know the girl you said I’d meet someday?
Well I got something to confess”

6. The Alan Parsons Project – “Sirius (Chicago Bulls Theme Song) “

This list wouldn’t be complete with the Chicago Bulls song.

Although “Sirius” wasn’t intended to be a basketball introduction song, it’s been an opening line up music since the Michael Jordan era.

7. Spoon – “Chicago At Night”

“Chicago At Night” is one of the alternative Chicago themed songs.

It has a touch of mystery and anticipation, so it’s a good song for exploring Chicago at night.

“But then she’d never been to Chicago at night before the fall
And it don’t stop not at all
It falls all around
In the city
Hits the ground.”

8. Buddy Guy – “Meet Me In Chicago”

“I got down a little bit of that down old music, Lord it’s been overdue
Got to get back to the windy city, with them funky ole sweet home blues
Meet me in Chicago, baby I’ll show you around
Meet me in Chicago, let me take you downtown.”

In a way, “Meet Me In Chicago” captures the essence and charm of Chicago.

The song mentions all the essential spots, and it will make you want to visit them right away.

9. The Blues Brothers – “Sweet Home Chicago”

“Come on, oh baby, don’t you wanna go?
Come on, oh baby, don’t you wanna go
Back to that same old place
Sweet home Chicago.”

This blues classic was first recorded by Robert Johnson in 1936.

It’s one of the famous songs about Chicago, and many artists recorded a cover version, including Eric Clapton.

But there’s something about The Blues Brothers’ version that makes us wanna dance in a bar somewhere on The Magnificent Mile.

10. Allister – “Somewhere on Fullerton”

Maybe Allister’s music is more to your liking.

They dedicated “Somewhere on Fullerton” to their hometown.

The song is full of youthful energy, early 2000s rock vibes, and nostalgic lyrics about Chicago.

“Somewhere down in Fullerton
There’s a place we used to go
To get away from it all.”

11. Elvis Presley – “In The Ghetto”

“In The Ghetto” is one of Elvis Presley’s songs that mention Chicago.

It’s a powerful song with heartfelt lyrics and a dreamy, sentimental melody.

“As the snow flies
On a cold and gray Chicago mornin’
A poor little baby child is born
In the ghetto.”

12. Chris Rea – “Chicago Morning”

“Chicago morning
Oh she’s a city of dreams
Chicago morning
Do you know what it really means?”

“Chicago Morning” captures the spirit of Chicago perfectly.

It’s a captivating blues track that will transport you to the streets of Chicago.

You might also find yourself having a drink in Kingston Mines.

13. Wilco – “Via Chicago”

Via Chicago” is a rather nostalgic song about Chicago and life challenges.  

The song starts peacefully, and becomes more intense towards the end.

It certainly conveys interesting emotions.

“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.”

14. Sun Kil Moon – “Sunshine in Chicago”

When it comes to alternative songs with Chicago in the title, Sun Kil Moon’s 2012 track definitely deserves a mention.

“Sunshine in Chicago” is a soothing song with dreamy indie vibes and peculiar lyrics. It’s exactly what you need.

“Sunshine in Chicago makes me think about my dad
It was eight or nine siblings I am told that he had.”

15. Patrick Stump and Lupe Fiasco – “This City”

“This City” is the first single from Patrick Stump’s (Fall Out Boy vocalist) debut solo album.

It was Stump’s way of paying tribute to his hometown.

And you can really feel his pride, especially because of the lyrics.

“‘Cause this city is my city
And I love it, yeah, I love it
I was born and raised here
I got it made here
And if I have my way, I’m gonna stay here.”

16. Crosby, Stills & Nash – “Chicago (We Can Change the World)”

“Chicago (We Can Change the World)” refers to anti-Vietnam war protests.

So, it’s a song with a rather serious message and a positive idea: we can change the world.

“Won’t you please come to Chicago for the help that we can bring
We can change the world rearrange the world.”

17. Aliotta Haynes Jeremiah – “Lake Shore Drive”

The local Chicago band Aliotta Haynes Jeremiah became popular because of their hit “Lake Shore Drive.

The band claimed that the lyrics of the song aren’t drug related. Therefore, it’s one of the Chicago city songs about the local lakefront driveway.

Nonetheless, it’s a really great tune.

And it’s a part of the famous Awesome Mix Vol.2 from “The Guardians of the Galaxy.”

“Running south on Lake Shore Drive heading into town
Just slippin’ on by on LSD, Friday night trouble bound.”

18. The Fratellis – “Chelsea Dagger”

If you’re from Chicago and you’re a fan of Chicago Blackhawks, then you know why “Chelsea Dagger” belongs on this list.

It’s the ice hockey team’s song, so it might as well be a Chicago theme song.

It’s an incredibly catchy and uplifting song too.

“Chelsea Chelsea I believe that when you’re dancing
Slowly sucking your sleeve
The boys get lonely after you leave
It’s one for the Dagger and another for the one you believe.”

19. Kanye West – “Homecoming”

Whether you’re a fan of Kanye West (sorry, Ye) or not, he recorded one of the best rap songs about Chicago.

He grew up in Chicago and attended Chicago State University for a year, before pursuing a career in music.

So, his love for Chicago is real.

Well, he named his daughter Chicago too.

20. Jimmy Rogers – “Chicago Bound”

The Chicago music scene has always been known for blues.

Therefore, we’re finishing this list with Jimmy Rogers’ blues gem from 1970.

The message of “Chicago Bound” is pretty clear:

“I’m gonna tell you something that you all should know
Chicago is the best place I ever know
I’m gonna stay in this town
I’m gonna live in this town
I’m gonna live in Chicago, it’s the greatest place around.”

Final Thoughts

It’s time to wrap it up.

We hope you enjoyed our selection of the best songs about Chicago.

It wasn’t an easy task though. When you dig deeper, you realize how many Chicago themed songs there are.

In a way, both citizens and visitors seem to be mesmerized by this city.

So, whether you’re traveling to Chicago or you’re nostalgic about your hometown, this playlist can put you in a Chicago state of mind.

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Will Fenton

Will, the founder of MIDDER, is a multifaceted individual with a deep passion for music and personal finance. As a self-proclaimed music and personal finance geek, he has a keen eye for futuristic technologies, especially those that empower creators and the public.

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