20 Songs About Chicago

Chicago, the heartbeat of Illinois, alive and pulsating with energy, joy, and pain. This vibrant city has inspired musicians to pen tracks inspired by the hustle of daily life to the echoes of its rich history. Curious to hear these sentiments? Check out the list and find out.

Chicago is one of the most populated cities in Illinois and is expanding by the minute. Like any location that is going through a burst of activity, Chicago too has had its share of issues. Songs about Chicago depict these conflicts, while others talk about sweet memories.

1. “Sweet Home Chicago” by Ben Harper, Tom Freund

This guitar-dominated tune is a rendition of “Sweet Home Chicago”. The musical arrangement gives a vibe of going on the road for a long time.

It’s very chill, the type of tune you would sing along carefreely with friends. And if you have a buddy who plays the guitar, then he can strum the accompaniments.

2. “Shy-Town” by Gorillaz

Under the innovative lyrics of Gorillaz, “Shy-Town” unfolds itself as a unique sonic representation of Chicago, colloquially known as Chi-Town. The angst in the lyrics paints a picture of an individual grappling with interpersonal issues, on the brink of breaking off a relationship that’s lost its charm.

3. “42 in Chicago” by Merle Kilgore

This 1960s country tune features a cool baritone voice. It talks about the extreme temperature in Chicago. Despite the heat, however, the protagonist is preoccupied with his relationship problems. The melody is lively and easy to sing along to.

4. “Chicago (Chi-Town) Blues” by Earth, Wind & Fire

In “Chicago (Chi-Town) Blues”, Earth, Wind & Fire crafts a musical atmosphere that’s as breezy and captivating as a cool Chicago wind. The delightful blend of vocals and wind instruments captures the soul of the city, resulting in a track that’s ideal for those moments when you just want to unwind and drift away.

5. “Sweet Home Chicago” by Robert Johnson

“Sweet Home Chicago” by Robert Johnson is more than just a song – it’s a journey. This blues classic, celebrated for its distinctive twelve-bar guitar arrangement and the masterful mix of treble and rhythm notes, takes listeners from California to Chicago, evoking the feeling of a cross-country road trip with a trusted companion.

6. “Everyday I Have The Blues / Goin’ To Chicago Blues” by The Four Tops

The Four Tops’ “Everyday I Have The Blues / Goin’ To Chicago Blues” is a vocal masterpiece in the rhythm and blues genre. The nuanced arrangement of this song, where the instruments are subtly played to allow the exceptional vocals to shine, presents an enticing harmony that will surely capture the hearts of blues lovers.

7. “Born In Chicago” by Paul Butterfield Blues Band

“Born In Chicago” from Paul Butterfield Blues Band’s 1965 self-titled album, channels the essence of the blues to tackle the sobering issue of gun violence. The narrative portrays a young man losing two friends to this escalating issue, thereby underlining the urgent need for societal change and awareness.

8. “Chicago” by Sufjan Stevens

This folk-rock song discusses the Sufjan Stevens experience in Chicago. The narrative is full of anecdotes that vary from good and bad experiences.

But in whatever classification, everything is just charged to as another life lesson. This song also received the honor to be the main theme of the online streaming platform production, “The Politician” which is proof of the appeal it has to diverse audiences.

9. “Tonight, Tonight” by Smashing Pumpkins

Straight outta Chicago comes “Tonight, Tonight” by Smashing Pumpkins. This alternative rock gem, conceived in a city studio, evokes themes of hope and courage. Its dreamlike quality resonated with fans and critics alike, garnering six awards out of eight nominations at the 1996 MTV Video Music Awards.

10. “Chicago At Night” by Spoon

This rock song is about the gloomy side of city life. The story begins with a young woman who travels to Chicago. She was still walking the streets at sunset and found herself confronting the wall which is slang for dying.

It’s speculated that the lady was murdered that night. The song warns listeners to be cautious when traveling alone in unknown territory.

11. “Chicago Seemed Tired Last Night” by The Hold Steady

“Chicago Seemed Tired Last Night” by The Hold Steady is an indie-rock piece that explores themes from spirituality to the energetic nightlife. It follows a man’s journey through Chicago, encountering a diverse array of individuals and discovering the city’s vibrant venues. This track delivers a varied taste of the city that never seems to sleep.

12. “Chi-City” by Common feat. Kanye West


“Chi-City”, a joint venture by Common and Kanye West, blends catchy intro beats with insightful lyrics. It centers around a man’s Christian faith and doesn’t shy away from criticizing rappers who lack substance, thus highlighting the need for purposeful compositions in the rap genre.

13. “Back To Chicago” by Styx

The 90s rock track “Back To Chicago” by Styx captures the yearning for home and loved ones. It follows the frustration of a man whose journey back to Chicago is disrupted, leaving him daydreaming about reuniting with his significant other.

14. “Dear Chicago” by Ryan Adams

“Dear Chicago” by Ryan Adams is a country tune that gracefully dances between past and present relationships. The lyrics beautifully convey a man’s heartache as he falls out of love with a woman from Chicago, embarking on a new chapter with a New Yorker.

15. “The Night Chicago Died” by Paper Lace

A siren-like sound greets the listener at the start of the song. The voices then come in gently and grow in intensity as the song progresses. It’s about nighttime gang fights on Chicago’s streets.

It even mentioned Al Capone and his defiance of the authorities. His father is a cop, and his mother is concerned since he is involved in the fights.

16. “Somewhere On Fullerton” by Allister

Allister’s high-energy punk rock anthem, “Somewhere On Fullerton”, is a vibrant ode to new encounters and good times. Filled with infectious rhythms that once made it a skaters’ favorite, this song narrates the exciting beginnings of a friendship fueled by fun.

17. “Chicago” by Win and Woo ft. Bryce Fox

Win and Woo’s “Chicago”, featuring Bryce Fox, oozes attitude. The song highlights the dichotomy of the Windy City, recognizing the conflicts yet expressing an unshakeable love for it. The sentiment in the lyrics insists on the need for action against the violence, reinforcing the protagonist’s resolve to stick around.

18. “Living In Chicago” by The Bee Gees

The arrangement of the song is light and relaxing to listen to. The strong guitar strums at the beginning give a sense of suspense. It talks about isolation and living alone. The tune advises to reach out and interact with people to lessen sorrow.

19. “Chicago Bound” by Jimmy Rogers

Jimmy Rogers’ bluesy melody “Chicago Bound” takes you on a heartfelt journey about a man’s life in the city of his birth. Possibly infused with Rogers’ personal feelings about his hometown, the song’s lively vibe, potent vocals, and captivating guitar riffs make it a compelling listen.

20. “South Side” by Moby feat. Gwen Stefani

The infectious rhythm of “South Side” by Moby, featuring Gwen Stefani, is amplified by the electric guitars’ resonant pulses. The song, inspired by Moby’s sojourns in Chicago, is a captivating electronic music gem that showcases the magic brewed when two talented artists collaborate.

Final Thoughts

The songs about Chicago tell a lot of history about the city. The stories are not all pleasant but what is interesting is that despite the hardships, the citizens of Chicago manage to thrive. These stories mirror the struggles and optimism of a city that faces its challenges head-on, affirming that progress is attainable with concerted effort.