Chicago, the Windy City, has inspired countless musicians with its vibrant history, iconic landmarks, and rich cultural tapestry. From jazz to blues, hip-hop to rock, the city’s influence spans genres and generations. Below, you’ll find 27 of the best songs about Chicago, celebrating its charm, struggles, and spirit.
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 timeless blues anthem is about the heart of the city’s musical legacy. Its catchy rhythm and enduring popularity have made it an unofficial theme song for Chicago.
2. “Chicago” – Sufjan Stevens
Lyric Sample: “I fell in love again, all things go, all things go.”
This heartfelt indie folk anthem appears on Sufjan Stevens’ critically acclaimed album Illinois. The lush instrumentation and poetic lyrics capture the hope and melancholy of starting anew in Chicago, making it a standout track.
3. “My Kind of Town” – Frank Sinatra
Lyric Sample: “My kind of town, Chicago is.”
Frank Sinatra’s iconic ode to Chicago highlights its friendly people and vibrant jazz scene. This classic song has become synonymous with the city’s enduring charm.
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 upbeat rock ballad celebrates the beauty of Lake Shore Drive, especially during a sunrise. It’s a nostalgic anthem for locals and visitors alike who cherish Chicago’s scenic routes.
5. “2120 South Michigan Avenue” – The Rolling Stones
Lyric Sample: Instrumental track
This blues-inspired instrumental pays tribute to the address of Chess Records, a historic Chicago recording studio. The Stones’ powerful grooves honor the city’s rich musical roots.
6. “Take Me Back to Chicago” – Chicago
Lyric Sample: “Take me back to Chicago, lay my soul to rest.”
This rock ballad from the band Chicago is about the simpler, heartfelt times in their namesake city. It’s a poignant 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 teams up with Saba to pay homage to Chicago, blending conscience and celebration. The song highlights both the struggles and resilience of the city’s people.
8. “Took Her to the O” – King Von
Lyric Sample: “Just got some top from this stripper bi**h, she from Kankakee”
King Von delivers a gritty narrative about the streets of Chicago in this hard-hitting rap track. It vividly portrays the raw realities of life in the city.
9. “In Chicago” – John Summit
Lyric Sample: Instrumental track
This dance hit celebrates Chicago’s vibrant club scene with its infectious beats. Its high-energy sound captures the nightlife that defines the city.
10. “South Side” – Moby ft. Gwen Stefani
Lyric Sample: “Here we are now going to the South Side.”
This electronic pop anthem references Chicago’s South Side while embodying an edgy, urban vibe. Its pulsating rhythm adds energy to any playlist.
11. “65th and Ingleside” – Chance the Rapper
Lyric Sample: “65th and Ingleside, way before Jamie got his tingles right.”
Chance is about personal growth and challenges in this heartfelt hip-hop track. The song captures his experiences in Chicago, blending nostalgia and gratitude.
12. “Dear Chicago” – Ryan Adams
Lyric Sample: “Dear Chicago, you’ll never guess.”
Ryan Adams delivers a somber ballad about love and heartbreak in the city. Its raw lyrics and haunting melody make it unforgettable.
13. “Only in Chicago” – Barry Manilow
Lyric Sample: “Love is in the air in Chicago.”
Barry Manilow’s “Only in Chicago” is a nostalgic ballad about love and memories tied to the city. The song highlights the magic and connection felt in Chicago, capturing the essence of a love that felt timeless and real, yet ultimately unrecapturable.
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.”
“Chicago (Is So Two Years Ago)” channels the raw emotion of a complicated relationship, blending frustration with nostalgic longing. The song captures the city’s pull, while expressing feelings of betrayal and unresolved anger, making it a powerful, anthemic tribute to the complexities of love and hometown ties.
15. “Chelsea Dagger” – The Fratellis
Lyric Sample: “Well, you must be a boy with bones like that.”
Though not explicitly about Chicago, this anthem is beloved by the city’s sports fans. It’s a staple at hockey games, fueling energy in Chicago’s arenas.
16. “Chicago Morning” – Chris Rea
Lyric Sample: “Chicago morning, are you lucky today?”
Chris Rea’s “Chicago Morning” paints a vivid picture of the city’s tough yet hopeful spirit. The song’s energetic beat and thoughtful lyrics capture the challenges and excitement of navigating life in Chicago, making it a perfect tribute to the city’s dynamic atmosphere.
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 hit is a soulful blues anthem that captures the emotional yearning to return to the city. With its heartfelt lyrics and Guy’s powerful delivery, the song is about a deep love for Chicago, blending nostalgia and longing for home.
18. “Chi-City” – Common
Lyric Sample: “And ya say Chi-City, we don’t stop, naw, we don’t quit.”
Common’s “Chi-City” is a powerful song about the struggles and resilience of Chicago. The song combines gritty verses with a celebration of the city’s vibrant culture, addressing both the challenges of urban life and the unbreakable spirit of its people.
19. “Go Cubs Go” – Steve Goodman
Lyric Sample: “Go Cubs go, hey Chicago, what do you say?”
This beloved anthem celebrates the Chicago Cubs’ victories 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.”
Louis Tomlinson’s “Chicago” is a song about lost love and the lingering connection between two people. The lyrics explore themes of regret, nostalgia, and the hope for reconciliation, with the city serving as a poignant backdrop for emotions that are still unresolved.
21. “Humors of Chicago” – The Tossers
Lyric Sample: Instrumental track
This Celtic punk tribute by The Tossers celebrates Chicago’s Irish heritage. With its fast-paced, folk-punk style, the track evokes the bustling atmosphere and vibrant culture of Chicago, making it a lively tribute to the Windy City.
22. “In the Ghetto” – Elvis Presley
Lyric Sample: “As the snow flies, on a cold and grey Chicago morn.”
Elvis Presley’s “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, while also conveying a sense of hope and the potential for change despite difficult circumstances.
23. “Chicago” – Portugal. The Man
Lyric Sample: “Chicago is dancing in xylophone laughter.”
“Chicago” by Portugal. The Man captures the city’s rebellious spirit with its energetic rock sound and deep lyrics. The song expresses themes of nostalgia and frustration, blending a sense of chaos with a deep connection to the Windy City, making it a raw and fitting tribute.
24. “Back to Chicago” – Styx
Lyric Sample: “I’m makin’ my way back to Chicago, I’m makin’ my way come rain or shine.”
“Back to Chicago” is a heartfelt rock ballad about returning home and seeking redemption in a relationship. The song is about the singer’s desire to make amends and find true love again, with the vibrant city of Chicago serving as the emotional backdrop for a fresh start.
25. “Chicago” – flipturn
Lyric Sample: “I’m going to Chicago, somewhere I don’t really know.”
flipturn’s “Chicago” is an indie rock anthem about seeking new experiences and escaping the monotony of life. The song captures the feeling of longing for something different, with Chicago representing both a literal and symbolic destination for change and self-discovery.
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. The lyrics capture the bittersweet longing for a time and feeling that has since faded, with the singer yearning to hold onto those memories forever.
27. “Saturday in the Park” – Chicago
Lyric Sample: “Saturday in the park, I think it was the Fourth of July.”
This classic by the band Chicago is about the city’s vibrant park culture. Its uplifting melody and celebratory lyrics make it a timeless tribute to Chicago’s community spirit.
Related: Songs About July and Best Songs About Summer
The Spirit of Chicago in Song
What makes songs about Chicago so special is their ability to capture its diversity and complexity. Each track shares a different aspect of the city, from its iconic landmarks to its vibrant culture and close-knit communities.
Whether it’s the soulful blues of “Sweet Home Chicago” or the rap anthem “Chi-City,” these songs celebrate the heart of the Windy City. They tell stories of resilience, pride, and a deep connection to a place that has inspired countless artists.
This rich musical legacy makes Chicago more than a backdrop, it’s the star of its own soundtrack. These tracks honor its history, culture, and the unique spirit that defines the city.
Conclusion: Chicago’s Musical Legacy
These 27 songs about Chicago showcase its vibrant spirit and enduring legacy. Whether you’re reminiscing about the Windy City or exploring its music for the first time, this playlist offers a journey through its soul.
If you’re interested in more music inspired by places and themes, be sure to check out our Best Songs About Race Horses or explore our Songs About Time article!