31 Best Songs About Chicago (The Windy City)

Chicago is referred to as The Windy City, and there are plenty of tracks that have been written as an ode or tribute to the city through the years. Here is our list of the 31 best songs about Chicago.

1. My Kind Of Town – Frank Sinatra 

My Kind Of Town (2008 Remastered)

First on our list is My Kind Of Town by Frank Sinatra, which is about Chicago, and it’s a tribute to what he considers to be his home. Released in 1964, this song has more than one version including multiple lyrical changes through the years. He talks about how friendly the people are and how everyone is always smiling. 

2. In The Ghetto – Elvis Presley 

Elvis Presley - In the Ghetto (Official Audio)

Next is In The Ghetto by Elvis Presley, which was released in 1969 on the album From Elvis To Memphis. This song is known as his comeback track, and the lyrics are haunting.

Written about a younger boy in Chicago, the song details how he grew up with a single mother and how hungry and poor his family is. He is eventually killed because he steals a car, and it goes into the violence and poverty that has stricken the community. This reached three on the Billboard Hot 100 chart, and it’s still just as relevant today as it was back then.

3. The Night Chicago Died – Paper Lace 

The Night Chicago Died

Calling all fans of That 70s Show, the song The Night Chicago Died by Paper Lace is up next. This track was written in 1974 and reached the top spot on the Billboard Hot 100 chart when it was released. It’s written from the perspective of a son who notices how nervous his mom is waiting for word on her cop husband in The Windy City. It was based on a fake shootout that happened between the Chicago Police Department and the gang of Al Capone.

4. Chicago Bound – Jimmy Rogers 

On our list is Jimmy Rogers with the hit Chicago Bound, which was released in 1970 on the album of the same name. This is a blues song about loving the city, and he calls it the greatest place ever. If you have ever been to Chicago, then you’ll enjoy this masterpiece that details why the city is so awesome. 

5. Take Me Back To Chicago – Chicago 

Take Me Back to Chicago

Next is Chicago with their hit song Take Me Back To Chicago, which is from the 1977 album Chicago XL. It’s a track that talks about the streets and summer breeze that you’ll find in The Windy City, and it’s a tribute song to the city. There are backing vocals on this track, which was by Chaka Khan, and it reached 63 on the Billboard Hot 100 chart.

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6. Bad Bad Leroy Brown – Jim Croce 

Bad, Bad Leroy Brown

One of the most well-known songs from Jim Croce is Bad Bad Leroy Brown, which was released in 1973 on his album called Life And Times. This track reached number one on the Billboard Hot 100 chart and that happened right before he suddenly died. It’s all about a fight in Chicago between a bartender and a shark in the gambling community. The barmaid is the subject of the fight, and it’s a song that you’ll go around singing all day. You can find this track in movies and television shows such as Friends. 

7. Dear Chicago – Ryan Adams 

Calling all soft rock fans, we’re going to talk about Ryan Adams and his song Dear Chicago, which is a sentimental track that talks about the city. He also talks about some of his previous loves and where he finds comfort. He still plays this song in his concerts even though it was initially released on his 2002 album Demolition. 

8. Born in Chicago – Paul Butterfield Blues Band 

In the movie Blues Brothers 2000, the song Born In Chicago is played, which is a great track about the Windy City. You may not know of Paul Butterfield Blues Band, but it’s a very good band that first released this song in 1965. It’s all about friends who ended up dying from what we can only assume was the gun violence that has long plagued the city. 

9. City In A Garden – Fall Out Boy 

Fall Out Boy - City in a Garden

Calling all punk fans, you might want to check out Fall Out Boy with the song City In A Garden, which was released in 2018 on the album Lake Effect Kid. This track is nothing short of a love song to the city. If you didn’t know, they are from Chicago, and during a tour, the band got to play at Wrigley Field to wrap up their tour, which they found to be mesmerizing. This track celebrates the city and what it has to offer, so it’s upbeat and could be considered an anthem for The Windy City. 

10. Chicago At Night – Spoon 

Up Next is Spoon with Chicago At Night, and it’s a song about what you might find in the city at night. The track was released in 2001 on the album Girls Can Tell, and it’s a timeless song that is mysterious and also very entertaining. 

11. Sweet Home Chicago – The Blues Brothers 

The Blues Brothers - Sweet Home Chicago (Official Audio)

In 1980, The Blues Brothers released Sweet Home Chicago, which can be found in the movie of the same name. Robert Johnson originally recorded this song in 1936, but The Blues Brothers’ version is amazing and deserves to be on this list. So many artists have covered this track through the years including Eric Clapton, but the fun and dance vibe from The Blues Brothers’ version reigns supreme.

12. Pulaski At Night – Andrew Bird 

'Pulaski at Night' - Andrew Bird

Next is the 2013 song Pulaski At Night by Andrew Bird, who is a local musician and the track is an ode to his hometown. This song comes from the album I Want To See Pulaski At Night. If you know anything about Chicago, then you know there is a Pulaski Avenue, and this track details his love of this area in The Windy City. He also is pleading with someone to come back to the city, although we don’t know who he is pleading with. 

13. Chicago – Crosby, Stills & Nash 

In 1971, Crosby, Stills & Nash released the song Chicago on their album 4 Way Street. This is a protest track about the 1968 convention and how the protesters were handled in Chicago. There is also mention of the Chicago 8, and it’s a heavy song that has a little gloom and doom but also some hope for the future with the refrain being about how we can change the world. 

14. Windy City – Phish 

PHISH : Windy City : {LIVE DEBUT} : {ONLY TIME PLAYED} : {720p HD} : Chicago, IL : 8/11/2009

Next is Phish with their song Windy City, which was released in 2009, and this track is special because it was only played live one time. The concert was at Toyota Park, and they sang this song to the crowd. In the track, a couch potato is just sitting there ordering things from the television, and it mentions how snowy the city is from the perspective of this guy sitting on his couch. 

15. Chi-City – Common 

Released in 2005 on the album Be, Chi-City by Common featuring Kanye West is all about Chicago and how much he loves his hometown. The grooves may be chill in this song, but the lyrics are anything but. It’s a look into what he experienced while in The Windy City.

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16. Only In Chicago – Barry Manilow 

Next on our list is Barry Manilow who released Only In Chicago in 1980, and this song is about everything you can find in Chicago that it’s known for, including deep dish pizza and the Sears Tower. Funnily enough, Earth, Wind & Fire’s Maurice White composed both the music and wrote the lyrics for this track. This upbeat funky song is a tribute to The Windy City and one of the best to listen to if you want to know what the city feels like. 

17. Showtime In Chicago – Joe Jackson 

Showtime In Chicago

Joe Jackson released Showtime In Chicago in 1988 on the album Tucker. As the name suggests, this song can be found in the movie Tucker: The Man And His Dream. It’s a cool track that is upbeat and has the jazz elements he was known for. 

18. Chicago Morning – Chris Rea 

Up next is Chicago Morning by Chris Rea, which was released in 2005 on his album Blue Guitars. This song is very blues-heavy and goes into all of the things you’ll find if you walk down the streets in Chicago. The track mentions Kingston Mines, which is a bar you can check out while you’re visiting. 

19. Sweet Home Chicago – Robert Johnson 

Robert Johnson - Sweet Home Chicago [1937]

Robert Johnson released Sweet Home Chicago in 1936, and this song references a lot of the streets and things that are found in Chicago. We had to mention the original version of the track since we brought up The Blues Brothers’ version, and this is where it all began. 

20. Meet Me In Chicago – Buddy Guy 

Meet Me in Chicago

Released in 2013, the song Meet Me In Chicago by Buddy Guy from the album Rhythm & Blues is going to make you want to visit all of the cool and trendy spots that Chicago has to offer. It’s a track that is a tribute to the city and will inspire you to go there and see it all for yourself.

21. Homecoming – Kanye West

Kanye West - Homecoming

Next on our list is Kanye West with his 2007 track Homecoming on the album Graduation. This is a must-listen song about Chicago, as we all know where he is from by now. This track reached 69 on the Billboard Hot 100 chart, 53 on the Hot R&B/Hip-Hop Songs chart, and 15 on the Hot Rap Songs chart. 

22. Tonight, Tonight – Smashing Pumpkins 

The Smashing Pumpkins - Tonight, Tonight (Official Music Video)

In 1995, Smashing Pumpkins released Tonight, Tonight on the album Mellon Collie And The Infinite Sadness, and this was one of the biggest tracks from this rock band. The song talks about how Chicago is the city by the lake, and it’s their hometown, so you know it’s going to be a positive anthem about The Windy City. 

The video for Tonight, Tonight was a huge staple of MTV in the 90s, and it won six different MTV awards. The track reached four on the Mainstream Rock chart and five on the Alternative Airplay chart. It peaked at 14 on the Adult Alternative Songs chart and hit 36 on the Billboard Hot 100 too. 

23. Lake Shore Drive – Aliotta Haynes Jeremiah 

Next on our list is Aliotta Haynes Jeremiah with the song Lake Shore Drive, which was the only track for this band to become a hit. This song was popular in the 60s and is an implication of LSD, based on the title of the track. The band claimed it has nothing to do with the drug, but it still became a song that people relate to LSD and the highways around Chicago. You can find this track in movies such as Guardians Of The Galaxy Vol 2 and Don’t Make Me Go

24. Via Chicago – Wilco 

Wilco released Via Chicago in 1999 on the album Summerteeth, and it talks a lot about Chicago, including the desire to go back home and missing people from that area. The song was inspired by the Henry Miller murder, and it’s an emotional track that’ll leave you inspired yet sad at the same time. A lot of people consider it to be their best song of all time. It has been featured in television shows such as The Bear. 

25. Chicago – Sufjan Stevens 

Sufjan Stevens - Chicago [The Politician Soundtrack Theme Song — OFFICIAL AUDIO]

Up next is Sufjan Stevens with the song Chicago from the 2005 album Illinois, and this is one of the best tracks about Chicago because it’s so beautiful. There are a lot of sentimental elements to this song, and it talks about starting over again and just leaving it all to create new beginnings.

26. Somewhere On Fullerton – ALLiSTER

ALLiSTER「Somewhere On Fullerton」

We have to mention Somewhere On Fullerton by ALLiSTER because this 2002 song from Last Stop Suburbia is awesome and an ode to The Windy City. They were a local punk band, and they talk about Fireside Bowl, which used to be where the punk rockers would have their shows, although it now hosts bowling instead. The band talks about how sad they are that this venue where all the bands used to play is now a bowling alley, and they aren’t happy about it at all. 

27. Boogie Woogie Bugle Boy – The Andrews Sisters 

Boogie Woogie Bugle Boy

Next is the 1941 song Boogie Woogie Bugle Boy from The Andrews Sisters, and this track is a big band song that is all about Chicago. In the track, the person from The Windy City has moved on from playing instruments in the city to playing for Company B in the army. It’s an infectious song that takes you back to that time in music, and while it has been covered a lot over the years, this version was put into the Grammy Hall of Fame

28. The El – Rhett Miller 

Rhett Miller released The El in 2002 on the album The Instigator, and this song is about the trains that go through Chicago and goes into funny detail about how the train rails sound. The lyrics also talk about how two people have been making out on the train and how they then broke up on the train, which sounds like it might be coming from personal experience although we don’t know that for sure. 

29. Chicago Bound Blues – Bessie Smith 

Chicago Bound Blues (Digitally Remastered)

Bessie Smith released Chicago Bound Blues in 1923, and she was one of the most well-known blues and jazz singers of that era. It’s a song that is about a woman taking her own life after she was left alone, and it’s sad and very dark. In the track, the narrator is talking about their feelings and thoughts after this experience.  It’s an ode to Chicago and fits the vocally-deep style that made her a sensation as one of the only African-American musicians to really make it big back then.

30. Sunshine In Chicago – Sun Kil Moon 

Sunshine in Chicago

Next up is a 2012 song called Sunshine In Chicago by Sun Kil Moon from the album Among The Leaves. This is a track that talks about the pleasant side of Chicago, and it’s very dream-like and has a lot of indie elements to it that you’ll enjoy. 

31. Crook County (Bone Crusher Mix) – Twista Feat. Newsense

Crook County (Bone Crusher Mix feat. Newsense)

Twista released Crook County (Bone Crusher Mix) in 1998 on his album Mobstability, and he is from that area, so he knows all of the bad things about Chicago. Given he has seen the horrible side of the city his entire life, this song is a warning about how you shouldn’t visit because it’s a risk to your health to do so.

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