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15 Beautiful Songs About Chicago

Carson suffers from a serious case of melophilia. Geeking out on her favorite music artists is her guilty pleasure.

These songs about Chicago best represents what the Windy City is all about.

These songs about Chicago best represents what the Windy City is all about.

Chicago is a city with a long and rich musical history. From the early days of jazz to the rise of rock 'n' roll, many different genres have called the Windy City home. As a result, there are many songs about Chicago, each of which captures a unique aspect of the city's character.

Whether you're looking for a slice of history or just a good tune, here are some of the best songs about Chicago that you will enjoy.

1. “My Kind Of Town” by Frank Sinatra

“My Kind of Town” is undoubtedly one of the most popular songs about Chicago. Frank Sinatra’s raspy voice and feel-good melodies are iconic, and the lyrics mention many of the things that make Chicago an incredible city.

From the “Union Stockyard” to Sinatra’s kind of “raz-ma-taz”, the song captures the essence of Chicago perfectly. It’s no wonder that the song has become an anthem for many locals and visitors alike. Whether you were born and raised in Chicago or just visiting for a weekend, “My Kind of Town” is sure to put a smile on your face.

2. “Take Me Back to Chicago” by Chicago

It's been said that home is where the heart is. And for the members of the band Chicago, there's no place like home. The band's song “Take Me Back to Chicago” is a nostalgic ode to their hometown, filled with images of simpler times and warm summer breezes.

The lyrics capture the essence of what it means to be from Chicago – from the city's bustling streets to its proud history. With its catchy melody and memorable lyrics, “Take Me Back to Chicago” is sure to strike a chord with anyone who has ever longed for a taste of home.

3. “Dear Chicago” by Ryan Adams

Ryan Adams’ “Dear Chicago” is a sentimental ballad about the comfort of living in Chicago and past loves. The song opens with a simple acoustic guitar melody, which is soon joined by Adams’ plaintive vocals.

The lyrics describe the speaker’s longing for a former love, and how the city of Chicago has become a symbol of their relationship. Throughout the song, Adams refers to the times he spent with his lover in different parts of the city. These references add an extra layer of meaning to the lyrics and help to paint a picture of the speaker’s nostalgia.

4. “Chicago” by Sufjan Stevens

Sufjan Stevens' song “Chicago” is a beautiful ode to the city of its namesake. The song speaks to the feeling of starting a new life after leaving everything behind, something that many people can relate to.

The lyrics are poignant and uplifting, and the overall tone of the song is one of hope and nostalgia. It is clear that Stevens has a deep love for Chicago, and this comes through in his music. “Chicago” is a moving tribute to a city that holds a special place in many people's hearts.

5. “Chicago at Night” by Spoon

“Chicago at Night” by Spoon is one of the more alternative songs about the city of Chicago. It was released back in 2001 as a part of the album ‘Girls Can Tell’. The song has a hint of both anticipation and mystery, which makes it a good choice for exploring Chicago at night.

The opening guitar riff is reminiscent of the band’s earlier work, but the rest of the song takes a turn into more atmospheric territory. The song reflects the band’s growth as artists and highlights their willingness to experiment with new sounds.

6. “Sweet Home Chicago” by The Blues Brothers

“Sweet Home Chicago” is a song written by American bluesman Robert Johnson in 1936. Ever since its release, the song has become a hit among Chicago residents.

The song is a typical dance number but the lyrics talk about how the singer wants to return to his sweet home in Chicago. In the early 1960s, the Blues Brothers recorded a cover of the song, which helped to popularize it among a new generation of listeners.

7. “Meet Me in Chicago” by Buddy Guy

“Meet Me in Chicago” by Buddy Guy is a love letter to the city of Chicago. The song captures the essence and charm of the city, and it mentions all the essential spots. The lyrics are full of pride and nostalgia, and it will make you want to visit the spots mentioned in the song right away.

The song starts with a question “Baby, don't you wanna go home” and then goes on to describe different places in the city. The song ends with a plea for the object of his affections to meet him in Chicago. “Meet Me in Chicago” is a fun and catchy song that will leave you wanting to visit the Windy City.

8. “Chicago Morning” by Chris Rea

Chris Rea's “Chicago Morning” is the perfect musical representation of the city of Chicago. The bluesy track transports listeners to the Windy City, evoking the feeling of walking along its bustling streets.

The song also captures the vibrancy of Chicago's nightlife, with a mention of the famous Kingston Mines nightclub. Rea's lyrics paint a picture of a city that is full of life and energy, making “Chicago Morning” the perfect ode to the Windy City.

9. “In the Ghetto” by Elvis Presley

“In the Ghetto” is a song written by Mac Davis and originally recorded by Elvis Presley. The song tells the story of a young boy growing up in the ghetto, and how he is ultimately killed in a gang-related shooting.

While the lyrics are bleak, they are also filled with hope, as the boy’s spirit lives on through his music. The melody is dreamy and sentimental, and Presley’s vocals are emotive and powerful. “In the Ghetto” is a beautiful and moving song that highlights the plight of inner-city youth.

10. “Sunshine in Chicago” by Sun Kil Moon

Sun Kil Moon's "Chicago" is a track off the band's 2012 album Among the Leaves. The song is a mellow, indie rock tune with solemn lyrics.

Mark Kozelek, the man behind Sun Kil Moon, wrote the song backstage before a show. He talks about the violence in Chicago and how it affects him personally. In spite of the dark subject matter, the music is dreamy and soothing.

The song has become a favorite among fans of alternative music. It is a unique and moving track that captures the city of Chicago in all its complex beauty.

11. “Back to Chicago” by Styx

In 1990, the rock band Styx released their album Edge of the Century. The final track on the album, “Back to Chicago,” told the story of a love affair between a singer who is constantly traveling and his lover whom he had left behind.

The lyrics were written by lead singer Dennis DeYoung, and the song was inspired by his own experience of being on the road and away from his family. While the song was a hit with fans, it was not well received by critics, who accused the band of selling out to commercialism.

12. “Chicago” by Michael Jackson

Five years after the death of Michael Jackson, Xscape released that had unreleased songs that he had recorded between 1983 and 2001. One of the songs on that album was “Chicago” that told the story of his passionate encounter with a Chicago girl.

The song starts with a simple, acoustic guitar riff that sets the tone for the rest of the track. Jackson's vocals are soft and emotive, giving the impression of a man telling a story by the fireside. However, as the song progresses, the instruments become more upbeat and electrified, culminating in a catchy chorus that is sure to get listeners singing along.

13. “The Night Chicago Died” by Paper Lace

“The Night Chicago Died” by Paper Lace is a song that describes the shootout between the Chicago police department and Al Capone’s gang in the 1920s. Although this is a fictional event, the lyrics make it feel real.

The song has been described as “an ode to classic gangster movies” and “a piece of American pop culture history.” It’s written from the perspective of a policeman’s son who watches anxiously as his mother waits for her husband on a night that doesn’t seem to end quickly.

14. “Leader of the Band” by Dan Fogelberg

Dan Fogelberg always looked up to his father and admired his talent as a musician. In 1981, Georgie passed away from cancer, and Dan decided to write a song in his honor. The result was “Leader of the Band,” a simple but beautiful ballad that told the story of Georgie’s life as a musician.

In the song, Dan referenced his father’s love for Chicago, which was where one of his brothers had moved after college. “Leader of the Band” remains a touching tribute to Georgie Fogelberg and is a reminder of the lasting influence a parent can have on their child.

15. “Only in Chicago” by Barry Manilow

“Only in Chicago” is a ballad written and composed by Maurice White and sung by Barry Manilow. The song tells the story of a love affair set against the backdrop of the city of Chicago.

The song describes the cityscape and how the love grew between two lovebirds. It’s a dream song about how two people fell in love and the impact of Chicago’s charm that brought them closer. Many people also consider this as a love letter to the city of Chicago because of its beautiful lyrics.

Chicago, Muse of Pop Culture

Chicago, the Windy City, has been the muse of popular culture for decades. From it’s humble beginnings as a trading post to it’s status today as one of the most populous and influential cities in the United States, Chicago has long held a place in America’s heart.

Songs about Chicago run the gamut from love letters to odes to specific neighborhoods, but they all share a common theme: this city has something special that keeps people coming back, again and again.

© 2022 Carson McQueen