20 Songs About Chicago

As a lifelong resident of Chicago, I’ve always felt that the city pulses with a rhythm all its own, a melody woven into the very fabric of our streets and neighborhoods. From the soulful notes of blues echoing through the South Side to the vibrant beats of hip-hop that resonate in our hearts, music is an inseparable part of what makes Chicago, well, Chicago.

In this playlist about Chicago, I want to take you on a personal journey through the soundscape of my hometown. Each song captures a unique facet of our city, reflecting its spirit, struggles, and triumphs. 

1. “My Kind of Town” by Frank Sinatra

“My Kind of Town” is a classic song performed by Frank Sinatra, originally composed by Jimmy Van Heusen with lyrics by Sammy Cahn. The song was featured in the 1964 musical film Robin and the 7 Hoods, where Sinatra’s character sings it in celebration after being acquitted of a crime. The song is a tribute to the city of Chicago, highlighting its people and institutions with repeated affirmations of “My kind of town, Chicago is” throughout the lyrics. Although it did not win the Academy Award for Best Original Song, it became one of Sinatra’s signature tunes and was included in many of his albums. The song’s upbeat tempo and affectionate lyrics capture the essence of Chicago’s vibrant spirit.

2. “All That Jazz” from the Musical Chicago

“All That Jazz” is one of the standout numbers from the musical Chicago, which debuted on Broadway in 1975. The musical, with music by John Kander and lyrics by Fred Ebb, is set in the 1920s and explores themes of crime, corruption, and media sensationalism in Chicago. “All That Jazz” serves as the opening number and sets the tone for the show with its lively and jazzy style, reflecting the era’s flapper culture and speakeasy atmosphere. The song encapsulates the glamour and grit of the Jazz Age, making it a timeless piece that has continued to captivate audiences through various productions and adaptations.

3. “Chicago” by Michael Jackson

“Chicago” is a song by Michael Jackson, originally titled “She Was Loving Me,” written by Cory Rooney. It was recorded during the sessions for Jackson’s Invincible album in 1999 but was not released until 2014 on the posthumous album Xscape. The track was reworked by producer Timbaland and features a deep-bass groove with Auto-tuned vocals. The song narrates a story of a romantic encounter in Chicago, where Jackson sings about a woman who deceives him by claiming she is unattached. The song’s contemporary production and Jackson’s emotive delivery highlight its modern appeal, even though it was initially recorded years earlier.

4. “Mrs. O’Leary’s Cow” by Brian Wilson

“Mrs. O’Leary’s Cow” is an instrumental piece by Brian Wilson, originally composed for the Beach Boys’ unfinished album Smile. The track, also known as “The Elements: Fire,” draws inspiration from the Great Chicago Fire of 1871, which folklore attributes to a cow owned by Mrs. Catherine O’Leary. Wilson created an experimental and avant-garde sound for this piece, incorporating unusual recording techniques to evoke the sensation of fire. The track was recorded with musicians wearing fire helmets and the studio filled with the smell of burning wood to enhance the atmosphere. Despite its unconventional nature, “Mrs. O’Leary’s Cow” earned Wilson a Grammy Award for Best Rock Instrumental Performance.

5. “Southside” by Common ft. Kanye West

“Southside” is a track by Common featuring Kanye West, from Common’s 2007 album Finding Forever. The song celebrates the South Side of Chicago, emphasizing the artists’ roots and experiences growing up in this part of the city. The lyrics, delivered by both Common and Kanye West, highlight their pride in their hometown and reflect on their personal journeys and successes. The song’s production, handled by Kanye West, features a soulful beat that complements the introspective and boastful verses. “Southside” is an anthem for Chicago’s South Side, capturing its cultural significance and the artists’ connection to it.

6. “The Night Chicago Died” by Paper Lace

“The Night Chicago Died” is a 1974 hit by the British band Paper Lace. The song tells a fictional story of a violent confrontation between Al Capone’s gang and the Chicago police. Set on the “East Side of Chicago,” the narrative describes a dramatic shootout that results in numerous casualties, though it is entirely fictional and not based on actual events. The song’s catchy chorus and dramatic storytelling helped it reach number one on the U.S. charts. Despite its historical inaccuracies, the song remains a memorable piece of pop music from the 1970s, characterized by its lively beat and engaging narrative.

7. “In The Ghetto” by Elvis Presley

“In The Ghetto” is a poignant song by Elvis Presley, released in 1969. Written by Mac Davis, the song addresses the cycle of poverty and violence in urban ghettos, with a specific reference to Chicago. The lyrics tell the story of a boy born into poverty who eventually falls into a life of crime, highlighting the social issues faced by many in similar circumstances. The song marked a significant moment in Presley’s career, as it was one of his first socially conscious recordings and helped revitalize his relevance in the music industry. “In The Ghetto” was both a commercial success and a critical commentary on societal issues, maintaining its relevance over the years.

8. “Chicago (That Toddlin’ Town)” by Frank Sinatra

“Chicago (That Toddlin’ Town)” is a song written by Fred Fisher in 1922 and popularized by Frank Sinatra. The song paints a lively picture of Chicago as a vibrant and bustling city, often referred to as a “toddlin’ town.” The lyrics celebrate the city’s dynamic atmosphere, mentioning landmarks like State Street and emphasizing the fun and excitement found in Chicago. Sinatra’s rendition of the song became iconic, capturing the spirit of the city and its cultural vibrancy. The song remains a classic tribute to Chicago, celebrated for its catchy melody and affectionate portrayal of the city.

9. “Back to Chicago” by Styx

“Back to Chicago” is a song by the American rock band Styx, featured on their 1990 album Edge of the Century. The song, written by band member Dennis DeYoung, reflects a theme of returning to one’s roots and finding solace in familiar surroundings. The lyrics convey a sense of humility and introspection, as the narrator acknowledges past mistakes and expresses a genuine desire to return to Chicago, a place that represents comfort and redemption. The song’s melodic rock style, combined with its heartfelt lyrics, makes it a poignant tribute to the city of Chicago and the personal significance it holds for the narrator.

10. “Stratford-On-Guy” by Liz Phair

“Stratford-On-Guy” is a track from Liz Phair’s critically acclaimed 1993 debut album Exile in Guyville. The song captures the experience of flying into Chicago at night, reflecting on the surreal and contemplative nature of air travel. The title is a play on Stratford-upon-Avon, combined with “Guyville,” a term used to describe the indie rock scene in Chicago. Phair’s lyrics are vivid and introspective, painting a picture of the city’s lights from above and the sense of detachment and clarity that comes with being physically removed from the ground. The song is celebrated for its simplicity and evocative imagery, making it a standout track in Phair’s discography.

11. “Born in Chicago” by Paul Butterfield

“Born in Chicago” is a blues song written by Nick Gravenites and performed by the Paul Butterfield Blues Band. It was the opening track on their self-titled debut album released in 1965. The song features a powerful blues harmonica and guitar riff, capturing the raw energy and spirit of Chicago’s blues scene. The lyrics tell a story of growing up in Chicago and the harsh realities faced by young people in the city, touching on themes of violence and survival. The song has become a blues standard, covered by numerous artists, and remains a significant piece in the history of Chicago blues music.

12. “Tonight, Tonight” by Smashing Pumpkins

“Tonight, Tonight” is a song by the Smashing Pumpkins, released as the third single from their 1995 album Mellon Collie and the Infinite Sadness. Written by lead singer Billy Corgan, the song is an orchestral rock anthem that speaks to themes of hope, change, and perseverance. The lyrics evoke a sense of renewal and optimism, with Corgan urging listeners to believe in themselves and embrace the possibilities of the future. The music video, inspired by Georges Méliès’ silent film A Trip to the Moon, adds a whimsical and nostalgic visual element to the song. “Tonight, Tonight” is a powerful and uplifting track that captures the band’s connection to their hometown of Chicago and its influence on their music.

13. “Lido Shuffle” by Boz Scaggs

“Lido Shuffle” is a song by Boz Scaggs from his 1976 album Silk Degrees. Co-written with David Paich, the song tells the story of a drifter named Lido who is constantly on the move, seeking his next big score. The lyrics describe Lido’s journey, including a stop in Chicago (“Next stop Chi-town, Lido put the money down, let it roll”), where he engages in gambling and other risky ventures. The song’s shuffle beat was inspired by Fats Domino’s “The Fat Man,” and it features a catchy, upbeat rhythm that complements the narrative of a hustler’s life on the road. “Lido Shuffle” became one of Scaggs’ biggest hits, reaching number 11 on the U.S. charts and showcasing his ability to craft compelling storylines through music.

14. “Bad, Bad Leroy Brown” by Jim Croce

“Bad, Bad Leroy Brown” is a song by Jim Croce, released in 1973 on his album Life and Times. The song became Croce’s biggest hit, reaching number one on the Billboard Hot 100. It tells the story of Leroy Brown, a brash and boastful man from the South Side of Chicago. The lyrics describe Leroy as the “baddest man in the whole damn town,” known for his flashy clothes, fancy car, and tough demeanor. However, his arrogance leads to his downfall when he picks a fight he can’t win. The song’s catchy melody and humorous storytelling make it a memorable tribute to a larger-than-life character from Chicago.

15. “Leader of the Band” by Dan Fogelberg

“Leader of the Band” is a song by Dan Fogelberg from his 1981 album The Innocent Age. The song is a heartfelt tribute to Fogelberg’s father, Lawrence Fogelberg, who was a bandleader and music teacher in Peoria, Illinois, near Chicago. While not explicitly about Chicago, the song reflects the influence of the city’s musical heritage on Fogelberg’s upbringing and career. The lyrics express gratitude and admiration for his father’s dedication to music and the impact it had on his own life. “Leader of the Band” became one of Fogelberg’s most beloved songs, resonating with listeners for its emotional depth and sincerity.

16. “Take Me Back to Chicago” by Chicago

“Take Me Back to Chicago” is a song by the band Chicago, featured on their 1977 album Chicago XI. Written by band member Danny Seraphine and David “Hawk” Wolinski, the song is a nostalgic reflection on the band’s roots in the city of Chicago. The lyrics express a longing to return to the city and recapture the spirit and experiences of their early days. The song features a smooth, jazz-influenced arrangement, highlighting the band’s signature blend of rock and jazz elements. “Take Me Back to Chicago” stands as a tribute to the band’s hometown and the formative role it played in their musical journey.

17. “65th & Ingleside” by Chance the Rapper

“65th & Ingleside” is a deeply personal song by Chance the Rapper, released in 2018 as part of a collection of singles. The song reflects on Chance’s early life and struggles while living on the South Side of Chicago, specifically at the intersection of 65th Street and Ingleside Avenue. The lyrics recount his journey from humble beginnings to achieving success, highlighting the support of his fiancée, Kirsten Corley, during tough times. The song’s hopeful and uplifting tone is underscored by the refrain “Made a way, out of no way,” which is a nod to the gospel saying “God will make a way when there seems to be no way” . The track showcases Chance’s ability to blend personal storytelling with broader themes of perseverance and faith.

18. “Only in Chicago” by Barry Manilow

“Only in Chicago” is a song by Barry Manilow that explores themes of nostalgia and reflection. The lyrics describe a return to Chicago to understand what went wrong in a past relationship and to recapture the feelings of happiness once experienced there. The song paints a picture of Chicago as a place where unique and meaningful moments occur, emphasizing the city’s special place in the narrator’s heart . The emotional depth of the song is enhanced by Manilow’s signature melodic style, making it a poignant tribute to the city and its impact on personal memories.

19. “I’m a Ramblin’ Man” by Waylon Jennings

“I’m a Ramblin’ Man” is a classic country song by Waylon Jennings, released in 1974. Written by Ray Pennington, the song narrates the life of a wandering musician who moves from place to place, leaving a trail of broken hearts. The lyrics mention Chicago as one of the many cities where the narrator has made a mark (“Well, up in Chicago, I was known as ‘Quiet Boy'”). Although the song is not exclusively about Chicago, it includes the city as a significant stop in the rambling man’s journey . The song’s upbeat tempo and Jennings’ charismatic delivery capture the restless spirit of a life on the road.

20. “City in a Garden” by Fall Out Boy

“City in a Garden” is a song by Fall Out Boy from their 2018 EP Lake Effect Kid. The song serves as a love letter to Chicago, the band’s hometown. The lyrics express deep affection and gratitude towards the city, celebrating its beauty and the sense of belonging it provides. The title “City in a Garden” refers to Chicago’s motto, “Urbs in Horto,” which means “City in a Garden” in Latin. The song highlights the band’s connection to Chicago and the inspiration they draw from the city’s vibrant culture and history . With its energetic rock sound and heartfelt lyrics, “City in a Garden” stands as a tribute to the place that shaped the band’s identity.

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