51 of The Best Songs about Chicago of All Time

Many things come to mind when thinking about the city of Chicago – Windy City, Second City, deep dish pizza, hot dogs with everything on them, and of course, some of the best music ever made.

The city has produced some of the most iconic musicians and bands in history, including the likes of Muddy Waters, Howlin’ Wolf, Buddy Guy, the Staples Singers, Curtis Mayfield, Earth, Wind & Fire, and of course, the one and only Chicago.

And while there are countless songs that the city has inspired, here are 51 of the most popular ones of all time.

Top Best Songs about Chicago

1. Sweet Home Chicago by Robert Johnson

Perhaps one of the most influential Chicago songs of all time, “Sweet Home Chicago” by Robert Johnson was originally performed with nothing more than an acoustic guitar.

Featuring a simple, yet catchy 12-bar blues progression, this song has been covered by countless artists over the years, including the likes of Eric Clapton and The Blues Brothers.

Today it has become an anthem for the city and is often performed by blues musicians in Chicago’s many clubs.

Key Lyrics

Now one and one is two, two and two is four
I’m heavy loaded baby, I’m booked, I gotta go
Cryin’, baby, honey, don’t you want to go
Back to the land of California, to my sweet home Chicago

2. Chicago by Frank Sinatra

Frank Sinatra was well known for his love of the city of Chicago, and he even shot one of his most famous music videos here, for the song “My Kind of Town (Chicago Is).”

But it’s his other ode to the city, simply titled “Chicago,” that makes this list. This toe-tapping tune features some of Sinatra’s signature crooning and is the perfect love letter to the city.

It’s overall a fairly simple song, but there’s something quite enjoyable about how Frank fondly sings of his hometown. 

Key Lyrics

Chicago, Chicago, that toddling town
Chicago, Chicago, I will show you around, I love it
Bet your bottom dollar you’ll lose the blues in Chicago, Chicago
The town that Billy Sunday could not shut down

3. Chicago by Michael Jackson

Released on the King of Pop’s posthumous album Xscape, “Chicago” by Michael Jackson is about a cheating wife he meets on his way to Chicago.

With production from Timbaland and J-Roc, the song sounds ridiculously smooth and pretty despite its darker subject matter. Very different from your typical Michael Jackson song, but a welcome change of pace for sure.

Key Lyrics

I met her on my way to Chicago
Where she was all alone and so was I
So I asked her for her name
She smiled and looked at me
I was surprised to see
That a woman like that was really into me

4. Homecoming by Kanye West

If you are from Chicago yourself or just missing home, this song will definitely resonate with you.

“Homecoming” by Kanye West is all about the city of Chicago and all the memories he has growing up there. It’s a pretty sentimental track, with Kanye even getting pretty emotional towards the end of the song.

But it’s definitely a feel-good track overall and will make you appreciate your hometown even more.

Key Lyrics

I’m comin’ home again
Do you think about me now and then? (Yeah)
Do you think about me now and then?
‘Cause I’m comin’ home again (Ow!)
-Min’ home again

5. Jesus Just Left Chicago by ZZ Top

Although not a hymn by any means, “Jesus Just Left Chicago” by ZZ Top is a rock and roll jam, which is surprisingly literal in what it means.

It talks about how even Jesus himself needed to get away from the city to other places in order to perform his miracles and do his work.

It’s a pretty tongue-in-cheek song that still manages to pack a punch with its catchy chorus and great guitar, bass, and drum work.

Key Lyrics

Jesus just left Chicago
And he’s bound for New Orleans
Well now, Jesus just left Chicago
And he’s bound for New Orleans, yeah
Working from one end to the other
And all points in between

6. Chicago Is So Two Years Ago by Fall Out Boy

This is one of the fan favorites from “Fall Out Boy’s” debut album, “Take This to Your Grave”. While the title might make it seem like it’s a diss track, it’s actually quite the opposite.

The song is all about how much fun the lead singer had while he was living in Chicago and how he’s struggling to find that same sense of fun and adventure in his current home.

It’s a pretty relatable track for anyone who’s ever left their hometown and is struggling to find their place in the world.

Key Lyrics

But there’s a light on in Chicago
And I know I should be home, all the colors
Of the street signs, they remind me of the
Pickup truck out in front of your neighbor’s house

7. Lake Shore Drive by Aliotta Haynes Jeremiah

While many have discussed what it means, “Lake Shore Drive” is actually a surprisingly accurate description of driving down Lake Shore Drive in Chicago.

A very simple song twisted into different meanings due to its title doubling as an apparent LSD reference. Featuring a simple piano melody and some light guitar work, this is a pretty sweet song with some hidden depth.

Key Lyrics

And there ain’t no road just like it anywhere I found
Running south on Lake Shore Drive heading into town
Just slippin’ on by on LSD, Friday night trouble bound

8. My Kind of Town by Frank Sinatra

Though we promised no repeats, we had to make an exception for this one. “My Kind of Town” is another Frank Sinatra song where he sings praises of the windy city but in a different light.

While he’s still singing of his love for the state, he also talks about his desire to go home to Chicago, where he feels happy.

It’s a bit more on the slow side than “Chicago” but features some fantastic horn work throughout the track.

Key Lyrics

My kind of town, Chicago is
My kind of town, Chicago is
My kind of people, too
People who smile at you
And each time I roam, Chicago is
Calling me home, Chicago is
Why I just grin like a clown
It’s my kind of town

9. In the Ghetto by Elvis Presley

A much darker song, “In the Ghetto” by Elvis Presley is about the cycles of poverty and violence that often plague inner-city neighborhoods.

As the name implies, it covers the darker aspect of Chicago, which often gets overshadowed by the city’s more positive aspects.

No doubt it is a heavy song, but definitely, an important one that highlights, things aren’t all sunshine and rainbows, even in a place like Chicago.

This is also Presley’s first Top 10 hit in over four years, so it’s clear that the song struck a chord with many people.

Key Lyrics

Well, the world turns
And a hungry little boy with a runny nose
Plays in the street as the cold wind blows
In the ghetto (In the ghetto)
And his hunger burns
So he starts to roam the streets at night
And he learns how to steal and he learns how to fight
In the ghetto (In the ghetto)

10. Born in Chicago by The Paul Butterfield Blues Band

Another darker take on Chicago living, “Born in Chicago” by the Paul Butterfield Blues Band tells about the lead singers’ hypothetical friends, all losing their lives in their younger years to the mean streets of Chicago.

Paired with an incredibly bluesy guitar riff and some great harmonica work, this song is both catchy and pretty depressing at the same time.

Key Lyrics

I was born in Chicago, nineteen and forty-one
I was born in Chicago in nineteen and forty-one
Well, my father told me
“Son, you’d better get a g*n.”
My first friend went down
When I was seventeen years old
Oh, my first friend went down
When I was seventeen years old
Well, there’s one thing I can say about that boy
He gotta go

11. Crook County by Speedknot Mobstaz and Twista

Here “Crook Country” refers to Cook County, which is the county that Chicago is located in. In this song, Speedknot Mobstaz and Twista put all of their energy into a passionate breakdown of all the things that make Chicago dangerous. 

An “in-your-face” track that really highlights the darker side of living in Chicago. There’s also a slight fondness behind it all, which is a fascinating touch for the song.

Key Lyrics

In the Chi, it’s kill or be killed, hussle or die
You gotsta take the pie, momma didn’t lie
Look in my eyes you see the realness
The nine makes you feel this

12. Chelsea Dagger by The Fratellis

“Chelsea Dagger” by The Fratellis is a unique case among Chicago-based songs because it doesn’t really mention Chicago at all.

But, it is the goal song for the ice hockey team the Chicago Blackhawks, making it a de facto anthem for the city.

It’s an incredibly catchy, upbeat rock song about a girl named Chelsea Dagger, who just happens to be a bit more than the lead singer bargained for.

Key Lyrics

Chelsea, Chelsea, I believe
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

13. Take Me Back to Chicago by Chicago

It only makes sense that the band Chicago would have a song on this list, and in this case, it’s the sorrowful song of longing, “Take Me Back to Chicago.”

In it, the lead singer sings about how when he dies, he wants to be put to rest in his hometown of Chicago. It goes on to touch on the many great things and nostalgic ideas of the state, ending with a longing, echoing chorus.

Key Lyrics

Take me back to Chicago
Lay my soul to rest
Where my life was free and easy
Remember me at my best
Take me back to Chicago
Where music was all I had
I tried to be good as I could
And sometimes that made me sad

14. Angels by Chance the Rapper

Known for his many charitable works, it’s no surprise that Chance the Rapper would have a song about helping those in need, which is exactly what “Angels” is about.

The song is Chance’s way of giving back to the city of Chicago, which has given him so much. He talks about how he is surrounded by angels, both figuratively and literally, and how they help to guide him and keep him safe.

Fellow Chicagoan Saba also joins him for a few verses, which just adds to the great message of the song.

Key Lyrics

They was talkin’, “Woo, this woo wap da bam”
City so damn great, I feel like Alexand’
Wear your halo like a hat, that’s like the latest fashion
I got angels all around me, they keep me surrounded

15. Southside by Common Ft. Kanye West

“Southside” is a banger from Common, featuring one and only Kanye West. The song is all about growing up on the south side of the city and all the struggles that come with it.

Despite its dark subject matter, the song is actually pretty upbeat and will definitely get your head nodding. Although not as popular as some of Common’s other songs, “Southside” is definitely a hidden gem in his catalog that showcases the talent of two of Chicago’s brightest stars.

Key Lyrics

We coming from the Southside, Southside
Southside, Southside
Southside, Southside
Southside, side of the Chi

Rap Songs about Chicago

Rappers have always been pretty vocal about where they’re from, and Chicago is no exception. From the city’s tough beginnings to its more recent successes, Chicago has been the muse for many a rapper. And while these songs might not all be positive, they definitely give an interesting perspective on what it’s like to live in the city.

  1. 65th and Ingleside – Chance the Rapper
  2. Chicago Legends – Fbg Duck
  3. Bow to the Masta – Kool Keith
  4. Chi‐City – Common
  5. Chi-Town – Da Brat
  6. Dennehy – Serengeti
  7. Epidemic – Polo G
  8. Full Moon – Common
  9. Get Busy – Mr. Lee
  10. Git On Up – Fast Eddie and Sundance

Kanye West Songs about Chicago

Of course, we couldn’t make a list of songs about Chicago without including at least one from the one and only Kanye West. Known for his love of his hometown, Kanye has mentioned Chicago in many of his songs. But these are some of the best:

  1. Everything I Am
  2. Southside
  3. All Day
  4. Homecoming
  5. Hey Mama
  6. Impossible
  7. Dark Fantasy
  8. Through the Wire
  9. Monster
  10. Don’t Like

Chance The Rapper Songs about Chicago

We all know that Chance The Rapper is one of the most vocal about his love for Chicago, and he’s got the songs to back it up. From his early mixtapes to his more recent album, The Big Day, Chance has always found a way to include Chicago in his music. Being a native of the city, it’s only natural that he would want to pay homage to the place that made him who he is. Here are some of his best songs about Chicago:

  1. I Might Need Security – Chance The Rapper
  2. 65th and Ingleside – Chance the Rapper
  3. Angels
  4. Dear Chicago Summer

Frank Sinatra’s Songs about Chicago

If you know then you know that Frank Sinatra loved Chicago. And that reflected in his music, with a number of his songs either being about the city or referencing it somehow. Some of the most popular ones are “My Kind of Town,” “Chicago,” and “That’s Life.” But really, any Sinatra song could be about Chicago and we wouldn’t be surprised.

  1. My Kind of Town
  2. Chicago

Rock Songs about Chicago

No list of songs about Chicago would be complete without at least one rock song. Rock music and Chicago have always had a pretty tight relationship, with a lot of famous bands getting their start in the city. For example, Cheap Trick, Smashing Pumpkins, and Wilco all have deep roots in Chicago. And while there are too many great rock songs about Chicago to count, here are a few of our favorites.

  1. 2120 South Michigan Avenue – Rolling Stones
  2. 5-3-10-4 – Maybe I’ll Catch Fire – Alkaline Trio
  3. Area 312 – Resurrection Band
  4. Back to Chicago – Styx
  5. Blue Line – Local H
  6. Bryn Mawr Stomp – Local H
  7. Chi-Town – The Cribs
  8. Chicago – Ingram Hill
  9. Chicago – The Purple Hearts
  10. Don’t Call On Me – The Monkees

Wrapping Up

So, there you have it: 50 of the best songs about Chicago of all time. From different genres and eras, these songs all capture what it’s like to live in the Windy City. So, whether you’re from Chicago or just a fan of great music, we hope you enjoy these songs as much as we do.