Chicago, the Windy City, has inspired musicians across every genre, from blues legends to modern rappers. These songs capture the city’s spirit, struggles, and neighborhoods in ways that only artists who know it can.
Be sure to check out the Songs About Chicago Playlist at the bottom of this page!
Best Songs About Chicago
1. “Sweet Home Chicago” – Robert Johnson
Lyric Sample: “Oh baby, don’t you want to go, back to the land of California, to my sweet home Chicago?”
This blues classic is about wanting to return to Chicago. It’s become an unofficial anthem for the city.
2. “Chicago” – Sufjan Stevens
Lyric Sample: “I fell in love again, all things go, all things go.”
This indie folk song is about falling in love again while driving between Chicago and New York. Stevens sings about the freedom found in mistakes and life on the road.
3. “My Kind of Town” – Frank Sinatra
Lyric Sample: “My kind of town, Chicago is.”
Sinatra’s classic is about loving everything Chicago represents: the people, the jazz, the whole vibe of the city.
4. “Lake Shore Drive” – Alliotta Haynes Jeremiah
Lyric Sample: “There’s a road I’d like to tell you about, lives in my hometown.”
This ’70s rock song is about driving Lake Shore Drive on Friday nights heading into town. It captures the feel of cruising along the water with the city lights ahead.
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5. “2120 South Michigan Avenue” – The Rolling Stones
Instrumental track
This blues-inspired instrumental pays tribute to the address of Chess Records, a historic Chicago recording studio.
6. “Take Me Back to Chicago” – Chicago
Lyric Sample: “Take me back to Chicago, lay my soul to rest.”
This rock ballad is about the simpler times in the band’s namesake city. It’s a reminder of the emotional ties to home.
7. “Angels” – Chance the Rapper
Lyric Sample: “I got angels all around me, they keep me surrounded.”
Chance the Rapper celebrates Chicago despite the city’s violence. He wants to clean up the streets so his daughter has somewhere safe to play.
8. “Took Her to the O” – King Von
Lyric Sample: “Just got some top from this stripper bi**h, she from Kankakee.”
King Von’s street narrative goes sideways when picking up a girl leads to shooting her ex. The track is chaotic violence told with dark humor.
9. “In Chicago” – John Summit
Instrumental track
This electronic dance track is a repetitive celebration of being drunk and high in Chicago’s club scene.
10. “South Side” – Moby
Lyric Sample: “Here we are now going to the South Side.”
Moby’s track is about riding through different sides of the city with weapons. The South Side gets called out specifically.
11. “65th and Ingleside” – Chance the Rapper
Lyric Sample: “65th and Ingleside, way before Jamie got his tingles right.”
Chance raps about his life before he made it. The song deals with guilt over lost time and trying to make things right.
12. “Dear Chicago” – Ryan Adams
Lyric Sample: “Dear Chicago, you’ll never guess.”
This ballad is written like a letter to Chicago, dealing with depression, loneliness, and a bleak outlook on the future.
13. “Only in Chicago” – Barry Manilow
Lyric Sample: “Love is in the air in Chicago.”
Manilow’s track is about a relationship that only worked in Chicago. It wasn’t just the person but something about the city itself that made it real.
14. “Chicago (Is So Two Years Ago)” – Fall Out Boy
Lyric Sample: “But there’s a light on in Chicago, and I know I should be home.”
This rock song is about resentment over a relationship gone wrong and the complicated feelings about home.
15. “Chelsea Dagger” – The Fratellis
Lyric Sample: “Well, you must be a boy with bones like that.”
Though not explicitly about Chicago, “Chelsea Dagger” is beloved by the city’s sports fans. It’s a staple at Blackhawks games.
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16. “Chicago Morning” – Chris Rea
Lyric Sample: “Chicago morning, are you lucky today?”
Rea’s song is about being tough enough for Chicago and being able to handle what the city throws at you.
17. “Meet Me in Chicago” – Buddy Guy
Lyric Sample: “Baby, don’t you wanna go home, back from the land of California to my sweet home Chicago.”
Buddy Guy’s classic blues cover is about longing for both a person and Chicago.
18. “Chi-City” – Common
Lyric Sample: “And ya say Chi-City, we don’t stop, naw, we don’t quit.”
Common celebrates Chicago’s resilience while calling out tired rap. He claims to be taking over the game and bringing real substance back to represent the city.
19. “Go Cubs Go” – Steve Goodman
Lyric Sample: “Go Cubs go, hey Chicago, what do you say?”
“Go Cubs Go” is what’s played after every Chicago Cubs victory at Wrigley Field. It’s a cheerful staple for baseball fans in the city.
20. “Chicago” – Louis Tomlinson
Lyric Sample: “So if you’re lonely in Chicago, you can call me baby.”
In “Chicago,” Tomlinson sings about an ex and asks whether enough time has passed for forgiveness.
21. “Humors of Chicago” – The Tossers
Instrumental track
The Tossers’ Celtic punk instrumental celebrates Chicago’s Irish heritage with fast-paced folk energy.
22. “In the Ghetto” – Elvis Presley
Lyric Sample: “On a cold and gray Chicago mornin’, a poor little baby child is born in the ghetto.”
“In the Ghetto” is a ballad that tells the story of a young boy growing up in poverty in Chicago. The song is about the harsh realities of life in the city’s rough neighborhoods.
23. “Chicago” – Portugal. The Man
Lyric Sample: “Chicago is dancing in xylophone laughter.”
This 2006 alt-rock track is about being frustrated with the system, taxes, and not being heard.
24. “Back to Chicago” – Styx
Lyric Sample: “I’m makin’ my way back to Chicago, I’m makin’ my way come rain or shine.”
Styx’s rock ballad is about returning to Chicago to fix a relationship and make amends.
25. “Chicago” – Flipturn
Lyric Sample: “I’m going to Chicago, somewhere I don’t really know.”
In this 2020 track, Flipturn uses the city as a symbol for escape and wanting something different from the monotony of life.
26. “Somewhere on Fullerton” – Allister
Lyric Sample: “Somewhere down on Fullerton, there’s a place we used to go to get away from it all.”
This punk rock track is about a special place in Chicago that once offered solace and escape.
27. “Saturday in the Park” – Chicago
Lyric Sample: “Saturday in the park, I think it was the Fourth of July.”
This 1972 classic captures a day in the park where strangers become part of something bigger. It’s about possibility and what happens when people let their guard down to celebrate together.
Related: Songs About July and Best Songs About Summer
Conclusion
These songs show Chicago from every angle, from blues clubs to street corners to parks. Each one tells a different story about what it means to live in, leave, or love the Windy City.
If you’re interested in more themed lists, be sure to check out the Best Songs About Los Angeles or the Best Songs About Time!
