The city of Chicago has inspired hundreds of musicians, as seen through the many songs about the city released over the years. Here are the best songs about Chicago ever.
“My Kind of Town” by Frank Sinatra
Song Year: 1964
There's always something good about the oldies, and “My Kind of Town” by Frank Sinatra tells it all. Chicago is the kind of town you can call it home. Sinatra describes the City of Chicago and why he's proud to call it home.
He admits the city is where people smile at you. According to the song, Chicago is the kind of town full of music. Sinatra sings that Chicago has all the jazz one might be looking for.
Sinatra also notes that Chicago will never let you down. From this track, one can conclude that Chicago is a great city to live and work in.
“Bad, Bad Leroy Brown” by Jim Croce
Song Year: 1973
“Bad, Bad Leroy Brown” is a song about a man called Leroy Brown. Jim Croce sings about how Leroy was the meanest man in the city. One can argue that Leroy was the villain in the city of Chicago that Croce sings about.
Croce describes Leroy as mean, and he says he even looked scary. He notes that he was mean, and no one wanted to mess around with him. He carried his gun in his pocket and a razor in his shoes.
“Chicago” by Sufjan Stevens
Song Year: 2005
It's easy to fall in love with the big city of Chicago. Sufjan Stevens sings about his love of the town in his track “Chicago.” While the song doesn't directly talk about Chicago, one can associate the track with the good life of the city.
Stevens sings about how he fell in love again. The lyrics leave listeners wondering whether he fell in love with someone or the city.
“In The Ghetto” by Elvis Presley
Song Year: 1969
“In The Ghetto” is a track that describes the brutal ghetto life most young men and women experience while growing up. Presley sings about a boy born in the ghetto, forced to fight for his life right from a tender age.
The mother has nothing to offer the young boy, and the worst part is that society doesn't provide the much-required helping hand.
As the boy grows up in the streets, he adapts and learns how to steal to survive. However, the story doesn't end well, as the boy is shot dead while trying to steal a car. The song sums up a sad story about surviving in the ghetto.
“Chicago Bound” by Jimmy Rogers
Song Year: 1970
Blues of the 1970s hit differently, and “Chicago Bound” by Jimmy Rogers will surely leave you reminiscing about Chicago. Rogers sings about moving from one city to another for a better life.
He left Georgia and thought he was Memphis bound. But he soon realizes Memphis isn't his place to be. He feels there's no love in the city, and he moves to Louis.
The same thing happens to him; he later feels Louis is not the best place for him. So, he moves to Chicago, where he finally feels it's the right place.
“Back to Chicago” By Styx
Song Year: 1990
“Back To Chicago” is a song about a man intending to move back to Chicago as he thinks about reconciling with his lover. Styx sings about a man ready to leave his lover but suddenly realizes he is unfair.
The man feels guilty about his actions towards the woman he loves and regrets everything. Styx sings about the man willing to make it up to his woman and ensure things work out for the better.
“Chicago” by Michael Jackson
Song Year: 2014
Michael Jackson maintained his fame even after his untimely death in 2009. In 2014, the track “Chicago” was released and went on to top the Billboard charts.
“Chicago” is about an encounter with a beautiful lady in Chicago. Michael sings that he met her on his way to the city.
The encounter was love at first sight, as Michael says he was surprised the girl fell for him. While the girl was truly in love, he lied to Michael, perhaps because of his money.
The two lovebirds kick things off, but Michael later realizes the woman is married with kids.
When her husband is at work and the kids are at school, she spends time with Michael.
The track illuminates a sad story of a married woman trying to live a double life, thinking dating a celebrity is cool. As such, it's one of the many songs about villains.
“Think” by Aretha Franklin
Song Year: 1968
While jamming on the songs about Chicago, “Think” by Aretha Franklin should be included in your playlist. Aretha was later nicknamed “Queen of Soul” in Chicago because she loved and had many ties to the city.
The track “Think” is about freedom in relationships. It talks about the freedom to make decisions even after one settles down in a relationship. Aretha says one should let their minds run wild and feel free despite the changes one might be going through.
“Take Me Back To Chicago” by Chicago
Song Year: 1977
The song “Take Me Back to Chicago” talks about a better life once in Chicago. Chicago, the band, sings about going back to Chicago when the times were greater and much more fulfilling.
The band admits that there was a time in Chicago when life was free and easy. As a result, they sing about returning to Chicago since life in Los Angeles is hard.
One can tell that the band sang about a dream of a better life when they were young. Life was easy when we were young, and growing up to adulthood and taking responsibility isn't easy.
“Chicago (That Toddlin' Town)” by Frank Sinatra
Song Year: 1957
Ever wondered how Chicago is different from other cities? Well, “Chicago” by Frank Sinatra tells it all – it's a city where you would want someone to show you around.
Sinatra joyfully sings that Chicago is a great city where people are full of life. He loves the city because the locals know how to let it loose and enjoy themselves fully. Chicago is his hometown, and he acknowledges there's so much to discuss in the great city.
While most people think of New York as the best city in the world, Sinatra sings that people do things differently in Chicago.
“Dear Chicago” by Ryan Adams
Song Year: 2002
“Dear Chicago” is an exciting and sad track about someone going through a breakup. Ryan Adams sings about an old love that he recalls.
Perhaps the term “Chicago” refers to the first love he remembers. He sings that life is simpler than ever but fluctuates between happy and sad moments.
It's also ironic that despite being happy love didn't work out, Ryan says he thinks about committing suicide. He continues to say he's sorry for all the good times and the warm kisses they shared. He even admits that he might die alone and sad at some point.
The man doesn't cope well with the breakup. It hurts him to think about the good times with his lover.
“The Night Chicago Died” by Paper Lace
Song Year: 1974
“The Night Chicago Died” is another interesting track about Chicago that tells the story of Al Capone, a gangster back in the day, and his shootout with the police.
The song was released during the 1970s, a time when the police had difficulty dealing with gangsters. Whether true or not, the story sheds light on what used to happen when gangsters tried to run the streets.
Like in the movies, people watched real battles between villains and the police. Paper Lace, the band, says the war only ended when the gang surrendered.
That's how dangerous the streets were in the 70s. But at the end of the day, innocent people lost their lives or were affected by the gruesome experience.
“Chicago At Night” by Spoon
Song Year: 2001
If you want to explore Chicago nightlife, this is the perfect track to add to your playlist. “Chicago At Night” by Spoon is a track about a girl who goes to the city for the first time.
She doesn't know her way around, and she finds herself lost. While there's a lot to interpret about this song, it's evident that one can lose a lot if they are new to the city and need help knowing where to go.
“Born In Chicago” by Paul Butterfield Blues Band
Song Year: 1965
This track hits differently if you were born in Chicago. The Paul Butterfield Blues band talk about the brutal way of life during their early days. They sing about surviving in the streets with guns. The band also sings, saying most of their friends went down.
The social message one can draw from the track is that crime left many innocent people dying. Teenagers had to survive and fight for their lives. But the good news is that the streets are now safer than before. The band even acknowledges that the rules are alright.
“Sweet Home Chicago” by The Blues Brothers
Song Year: 1980
“Sweet Home Chicago” is the perfect jam to add to your playlist if you're traveling home to Chicago. This track was a major hit in the 1980s as it topped the charts.
The Blues Brothers trigger an exciting feeling about going home to Chicago. It's a great feeling to know that you're traveling to a place where you created memories with the person you love.
Did you know that the former president, Barrack Obama, sang this song in a memorable live performance in 2014?
“Meet Me In Chicago” by Buddy Guy
Song Year: 2013
Do you think about the sweet old blues from Chicago? Well, “Meet Me In Chicago” is a track that reminds one of the great songs released about Chicago.
Most artists sang about the great city of Chicago as it was the best place to be. This track also reinforces the same message about touring the great city. Buddy Guy tells his lover to meet him in Chicago, the only place to create the best memories and enjoy their lives together.
“Dancing in the Street” by Martha and the Vandellas
Song Year: 1964
“Dancing In The Street,” written by Marvin Gaye, Ivo Jo Hunter, and William Stevenson, was one of the best R&B/Soul music of 1964. The track ranked top 5 on the UK Singles Chart right after its release.
The title of the track gives you a hint that the song is about dancing to the groove. It centers around dancing in Chicago streets and other cities like New York and New Orleans.
The song's release sparked a growing interest in the R&B/Soul genre of music. Martha and her band sing about the idea that the time is right to sing in the streets with great upcoming songs.
“Somewhere” on Fullerton by Allister
Song Year: 2002
Rock lovers will find “Somewhere on Fullerton” quite interesting. The track deserves a spot on this list as it discusses The Fireside Bowl in Chicago.
According to the lyrics, this is a place the band used to visit while they tried to escape everything happening around them and find themselves.
“Tonight, Tonight” by Smashing Pumpkins
Song Year: 1995
“Tonight, Tonight” is another perfect rock song to add to your list of songs about Chicago. The track describes the city by the lake, which is Chicago. The lyrics indicate that the band sings about the amazing Chicago nightlife.
The band sings, saying they'll make memorable moments tonight. It's about letting go, enjoying yourself in the city, and taking in all it has to offer.
“Chicago Morning” by Chris Rea
Song Year: 2005
The “Chicago Morning” song describes the city as the city of dreams. Chris Rea asks the questions in this track, wondering whether you're up for the challenge in Chicago.
There are many ways to interpret the lyrics of this song. Chris talks about taking advantage of opportunities in the city.
“Sunshine in Chicago” by Sun Kil Moon
Song Year: 2012
“Sunshine in Chicago” is a happy yet sad jam about the good and the bad things to remember about Chicago. Sun Kil Moon sings about what the sunshine in Chicago reminds him about.
It's his father's hometown, where his old band used to play and have fun. But things have changed, and all the good times are nothing but memories.
“Via Chicago” by Wilco
Song Year: 1999
“Via Chicago” is a sad song that is somewhat distressful as the lyrics talk about killing someone and feeling good about it. Wilco sings about watching someone bleed to death and burying them alive.
The track is about the bitter emotions a man has towards his ex-lover. Now that they parted ways, Wilco sings that he's going home via Chicago.
“Only in Chicago” By Barry Manilow
Song Year: 1980
Barry Manilow has a long list of amazing tracks that topped the charts in the 1980s. “Only In Chicago” is a song about the city's uniqueness near the lake.
According to Barry, it's only in Chicago where love is in the air. There's plenty of magic in Chicago, and it's the ideal city to fall in love with another person or the city itself.
“This City” by Patrick Stump and Lupe Fiasco
Song Year: 2011
In this soul-punk genre of music, Patrick Stump pays tribute to his hometown, Chicago. Stump, a Fall Out Boy member, sings about being born and raised in a city he loves.
While he doesn't mention the city's name in the track, it's where he grew up alongside other band members.
“Boogie Woogie Bugle Boy” by The Andrews Sisters
Song Year: 1941
The song “Boogie Woogie Bugle Boy” might be old, but it has been performed by many artists worldwide, and it's one of the most popular songs about Chicago.
The song is about a famous trumpet man from Chicago with a unique style. Based on the song's lyrics, the man was good at his craft. The talented fellow took his craft to the army, where he entertained men in the military.
“Chelsea Dagger” by The Fratellis
Song Year: 2006
Folks from Chicago can easily resonate with the “Chelsea Dagger” song.
Over the years, the track has been the Chicago Blackhawks' theme song. If you're a fan of ice hockey sports, then you must have heard this rock song.
It's a fun song that used to drive fans of other hockey teams mad during the Blackhawks' great Stanley Cup wins in 2013 and 2015.
“Stratford‐on‐Guy” by Liz Phair
Song Year: 1993
It feels good when you're flying above a water body that transforms the appearance of the sky. That's part of the Chicago's beauty Liz sings about in this track.
From above, the city by the lake is very beautiful. Generally, the track offers a good description of how Chicago feels from the air when all its neighborhoods are presented to the eye.
“Homecoming” by Kanye West
Song Year: 2007
“Homecoming” was, and still is, one of the best songs about the great city of Chicago. Kanye doesn't mention “Chicago” in the lyrics but uses the city's nicknames, such as Windy and Chi-Town.
He sings about coming home to a place he keeps thinking about. The rich lyrics also describe Kanye's love for the city and how much he enjoyed living there.
“Lake Shore Drive” by Aliotta Haynes Jeremiah
Song Year: 1971
“Lake Shore Drive” is a song about the Lake Shore Drive expressway in the Windy City. The track talks about the road's uniqueness and why it's one of the best places to be.
Jeremiah shows how he has never found a road like Lake Shore Drive. This song has been featured in top movies like Don't Make Me Go and Guardians Of The Galaxy 2.
“Sweet Home Chicago” by Robert Johnson
Song Year: 1937
Unsurprisingly, songs about Chicago can be traced back to the 1930s. Robert Jackson sings to his girlfriend, urging her to go home to Chicago.
He describes Chicago as a “sweet home,” indicating that it's an old place with sweet memories of his past. Returning with a lover, he wants to start living in the city again and be at peace.
“65th and Ingleside” by Chance The Rapper
Song Year: 2018
Chance the Rapper sings about Ingleside Avenue in Chicago. It's a place he used to live with his ex-girlfriend. He went through a breakup, but he sings believing that everything will be okay despite the challenges he's going through.
Relationships can be complicated, but from this song, you can learn that it's all about looking at things from the positive side. Expecting things to work out for the best gives you hope.
“Lido Shuffle” by Boz Scaggs
The song “Lido Shuffle” also talks about Chi-town and why it deserves a visit. Boz Scaggs sings, saying the city is worth experiencing.
As a musician, Chicago is the best place to host shows and various entertaining activities. The city is the land of opportunities, which is what most of the artists in this list sing about.
“City In A Garden” by Fall Out Boy
Song Year: 2018
Fall Out Boy hails from Chi-City, and with this track, the band can't stop expressing their gratitude and sincere love for the city.
From their perspective, Chicago is like going home to a place that makes them feel the summer fling. The band expresses an undying love for the city that lights them up.
“Leader of the Band” by Dan Fogelberg
Song Year: 1981
“The Leader Of The Band” by Dan Fogelberg is a tribute to his father, thanking him for the love and support he gave him growing up. Dan says that without him, he would never have pursued his music career and might have headed off to Chicago like his brother.
He says his father passed him a special gift he can't repay. Dan s ings, saying that despite his father growing old, his song remains in his soul, and that's what he is most grateful for.
“Chi-City” by Common feat. Kanye West
Song Year: 2005
Common and Kanye West collaborated to release this hit song about Chi-City.
The song doesn't talk much about Chicago, but it's a message to other rappers that they should release songs with substance and purpose. However, it is Chicago-centric since Kanye has always had a great deal of love for the city in his heart – and goes so far as to say that the future of rap is Chicagoan.
“South Side” by Moby feat. Gwen Stefani
Song Year: 1999
Moby and Gwen Stefani sing about their experience touring South Side, Chicago. The thrilling experience is well explained in the lyrics.
The artists sing about taking a wild adventure all night long with their friends. Their excitement and fear of possibly dying suggest their fun is going to be raucous.
“Chicago” by Bryce Fox and Win and Woo
Song Year: 2017
“Chicago” by Bryce Fox and Win and Woo is a song about a war that's still not over. It's unclear what the artists meant in the lyrics, but they express their desire for something greater.
The dark lyrics suggest whatever they’re going through can’t easy be blown away, even with all the wind Chicago is famous for.
“Pulaski at Night” by Andrew Bird
Song Year: 2013
It's quite clear Andrew Bird sings about Chicago as the title of the track “Pulaski” refers to a street in the city and reflects on returning to the city of light. He also mentions the idea of starting over, perhaps hinting that the person he cares about was once disappointed with Chicago.
“Cold Windy City Of Chicago” by Boxcar Willie
Song Year: 2000
In this track, Boxcar Willie admits that Chicago wonders how one could ever be alone in the Windy City. With so many people, he expects that one should have many friends in a city as big as Chicago. Despite that, the narrator quips about not being able to afford a cup of coffee – ironic, given coffee stores are a great place to meet people.
“All That Jazz” by Chicago the Musical Australia
Song Year: 2019
“All That Jazz” was written in 1975, but it was performed by Chicago the Musical Australia in 2019. This jazz track describes all the good things about Chicago, including its culture and amazing nightlife. Despite praising the city, the song also mentions something about the bad side of the city, including issues like corruption and crime.
“Jesus Just Left Chicago” by ZZ Top
Song Year: 1973
“Jesus Just Left Chicago” has a spiritual dimension to it as it talks about Jesus leaving Chicago and he's bound for New Orleans. If you're a blues fan, this track will surely bring back some good old memories about the city. It ends on a positive note, highlighting that you shouldn't worry because Jesus is taking care of everything.
“The El” by Rhett Miller
Song Year: 2002
In this track, Rhett Miller sings about “The El,” which is Chicago's train system. He sings about the different feelings and thoughts a traveler has when using the train system. For instance, he talks about riding next to a stranger or making out under the El. The lyrics of this track will leave you curious about what really happens when one travels along the El in Chicago.
“We're All Crazy in Chicago” by Jonathon Brandmeier
Song Year: 2021
Jonathon Brandmeier sings about the wild fun that is in Chicago. He talks about the excitement of being associated with the great city. Jonathan repeats one line, saying everybody is crazy in Chicago. If you're looking to reveal the crazy side of you, then Chicago is the place to be.
Top Songs About Chicago, Final Thoughts
At this point, you can tell that Chicago is indeed a great city. Musicians have been singing about the city by the lake since the 1930s, and stories are still left to tell.
Today, contemporary songs still talk about the marvelous land of opportunity that is Chicago. Besides adding these tracks to your playlist, Chicago is worth visiting!