108 Songs About Chicago (Pop, Rap & More)
Contents
I. Country Songs About Chicago
1. Saturday in the Park by Chicago
The song is about a man who is enjoying a Saturday in the park with his friends and family. He is happy and content with his life, and he is looking forward to the future.
2. Hard to Say I’m Sorry by Chicago
The song is about a relationship that is on the rocks and the person singing is trying to save it. They admit they were wrong and are willing to do whatever it takes to make things right.
3. You’re the Inspiration by Chicago
The song is about a couple that has been through a lot together and has come out stronger because of it. They attribute their strength to each other, and say that they are the inspiration for each other.
4. Look Away by Chicago
The song is about a man who is in love with a woman who is in love with someone else. The man is trying to get the woman to look away from the other man and see him instead.
5. 25 or 6 to 4 by Chicago
The song is about a musician who is up all night trying to write a song. He is struggling to come up with the right words and is feeling frustrated. However, he eventually comes up with the perfect melody and lyrics.
6. If You Leave Me Now by Chicago
The song is about a man begging his lover not to leave him. He pleads with her to stay and promises that he will change and make things right. He is willing to do anything to keep her from leaving.
II. Latest Songs About Chicago
1. Dialogue by Chicago
“Dialogue” is a song by the American rock band Chicago. It was released as a single in 1971 and peaked at number 30 on the Billboard Hot 100 chart. The song was written by band member Robert Lamm and was included on the band’s fourth studio album, Chicago IV (1972).
2. If This Is Goodbye by Chicago
The song is about a couple breaking up and the man trying to convince the woman to stay. He talks about all the good times they’ve had together and how he’s going to miss her.
3. Chicago Lyrics by Chicago
The song is about the city of Chicago and how it is a great place to live. The lyrics talk about all the different things that make the city great, including the people, the food, the architecture, and the skyline.
4. Magic by Sprado
The song is about a young man who is in love with a girl who is in love with someone else. The young man is trying to use magic to make the girl fall in love with him, but he is having trouble because he doesn’t know how to do it.
5. 65th & Ingleside by Chance the Rapper
“65th & Ingleside” is a song by American rapper Chance the Rapper. It was released on October 31, 2016, as the lead single from his third mixtape, Coloring Book (2016). The song features guest vocals from singer-songwriter Saba. The song was produced by Nate Fox, Peter Cottontale, and Francis Starlite of the band Francis and the Lights.
6. City in a Garden by Fall Out Boy
“City in a Garden” is a song by American rock band Fall Out Boy. It was released on May 6, 2013, as the fourth single from their fifth studio album, Save Rock and Roll (2013). The song was written by the band’s lead vocalist and guitarist Patrick Stump and produced by Butch Walker. “City in a Garden” is a power pop and pop punk song with influences of new wave and synth-pop. Lyrically, the song is about the band’s hometown of Chicago and its relationship with the rest of the world.
The song received positive reviews from music critics, who praised its anthemic nature and catchy hook. Commercially, “City in a Garden” peaked at number 24 on the US Billboard Alternative Songs chart. The song’s accompanying music video was directed by Nathan Frankowski and features the band performing in various Chicago landmarks.
7. Chicago by Win and Woo, Bryce Fox
The song is about a relationship that ended badly and the singer is reflecting on what went wrong. He blames himself for not being able to make it work and wonders if he will ever find love again.
8. Jackson Park El Train by Harold Mabern Trio
The song is a jazz composition by Harold Mabern. It is a slow, mellow tune with a smooth, flowing feel. The melody is simple and catchy, and the overall mood of the song is peaceful and calming.
9. Vacation In Chicago by Cold War Kids
The song is about a person’s experience vacationing in Chicago. The person talks about all the different things they did while in the city, including visiting the zoo, going to the top of the Sears Tower, and riding on the Ferris wheel. They also mention all the different food they ate, including hot dogs, pizza, and ice cream.
III. Christian Songs About Chicago
1. Hillsong UNITED by Hillsong UNITED
The song “Hillsong UNITED” is a worship song written and performed by the Australian band Hillsong UNITED. The song is a declaration of the band’s faith in God, and a call to worship Him. The song is based on the scripture from Psalm 95:6, which says, “Oh come, let us worship and bow down; let us kneel before the Lord our Maker.” The song is a powerful and uplifting anthem of praise and worship, and is sure to inspire listeners to worship God with all of their heart.
2. Chris Tomlin by Chris Tomlin
The song ‘Chris Tomlin’ by Chris Tomlin is a song about the singer’s faith in God. Tomlin sings about how God has been there for him through everything, and how He is the only one who can provide peace and comfort.
3. Chris Tomlin by Chris Tomlin
The song ‘Chris Tomlin’ by Chris Tomlin is a song about the singer’s faith in God. Tomlin sings about how God has been there for him through everything, and how He is the only one who can provide peace and comfort.
IV. Rock Songs About Chicago
1. You’re the Inspiration by Chicago
The song is about a couple that has been through a lot together and has come out stronger because of it. They attribute their strength to each other, and say that they are the inspiration for each other.
2. Saturday in the Park by Chicago
The song is about a man who is enjoying a Saturday in the park with his friends and family. He is happy and content with his life, and he is looking forward to the future.
3. Make Me Smile by Chicago
The song is about a person who is struggling and feeling down, and how the person they love can make them smile again.
4. Dear Chicago by Ryan Adams
“Dear Chicago” is a song by Ryan Adams from his album Gold. The song is written as a letter to the city of Chicago, and Adams reflects on his time living there. He talks about the good times and the bad times, and how the city has changed over the years.
5. In the Ghetto by Elvis Presley
The song is about the struggles of living in the ghetto and the cycle of poverty and violence that exists there.
6. Somewhere on Fullerton by Allister
The song is about a guy who is in love with a girl who is in love with someone else. The guy is trying to figure out what to do and how to tell the girl that he loves her.
7. Chicago by Sufjan Stevens
The song is about the city of Chicago and how it is a great place to live. The singer talks about how the city has a lot to offer and how it is a great place to raise a family.
8. Born in Chicago by The Paul Butterfield Blues Band
The song is about growing up in Chicago and the tough times that the city can offer. Despite the hardships, the city is still home to the singer and they wouldn’t want to live anywhere else.
9. Lake Shore Drive by Aliotta Haynes Jeremiah
“Lake Shore Drive” is a song written by Aliotta Haynes Jeremiah and performed by Aliotta Haynes Jeremiah. The song is about a drive down Lake Shore Drive in Chicago.
10. Take Me Back to Chicago by Chicago
The song is about a person who is homesick for Chicago. They miss the city and all it has to offer. They want to go back and experience it all again.
11. 25 or 6 to 4 by Chicago
The song is about a musician who is up all night trying to write a song. He is struggling to come up with the right words and is feeling frustrated. However, he eventually comes up with the perfect melody and lyrics.
12. Sweet Home Chicago by Robert Johnson
The song is a blues ballad about a man’s love for the city of Chicago. The man is homesick for the city and its people, and he sings about how much he misses it.
13. Colour My World by Chicago
The song is about being in love and the various colors that represent different aspects of that love. The colors represent different emotions and situations that the person experiences while in love. The song is about the different stages of love and how each color represents a different stage.
14. Beginnings by Chicago
The song is about starting over and beginning again. It is about taking chances and making mistakes. It is about learning and growing.
15. Via Chicago by Wilco
“Via Chicago” is a song by Wilco from their fourth album, Summerteeth. The song is about a man who is struggling with his mental health and feeling like he’s losing touch with reality. The song is written in the first person and is written in a stream of consciousness style. The song reflects on the city of Chicago and how it can be a tough place to live. The song also touches on themes of addiction and depression.
16. If You Leave Me Now by Chicago
The song is about a man begging his lover not to leave him. He pleads with her to stay and promises that he will change and make things right. He is willing to do anything to keep her from leaving.
17. Pulaski at Night by Andrew Bird
The song ‘Pulaski at Night’ by Andrew Bird is about a man who is driving through the city at night. He is thinking about his life and how it has changed. He is thinking about the people he has met and the places he has been. He is also thinking about the future and what it might hold for him.
V. R&B Songs About Chicago
1. Do I Do by Peter White
The song is about a man who is in love with a woman who does not love him back. He is trying to figure out what he did wrong and why she does not love him.
2. All Night Long by Mary Jane Girls
The song is about a woman who is talking about how she is going to party all night long. She is going to dance and have a good time.
3. Born in Chicago by The Paul Butterfield Blues Band
The song is about the city of Chicago and how it is the birthplace of the blues. The song talks about how the city has a rich history of blues music and how it has influenced many artists.
4. For the Love of Money by The O’Jays
The song is about the love of money and how it can corrupt people. The song talks about how money can make people do things that they would never do otherwise, and how it can make them lose sight of what is important in life.
5. Chi‐City by Common
“Chi-City” is a song by American rapper Common, released on February 7, 2005 as the lead single from his sixth album, Be (2005). The song, which was produced by Kanye West, features a sample of the 1971 song “I’m New Here” by Gil Scott-Heron. Common’s lyrics discuss his hometown of Chicago and its residents, as well as his own experience growing up in the city. The song received positive reviews from music critics, who praised its production and Common’s lyrics.
6. Lake Shore Driving by Duran Duran
The song is about a man who is driving along the shore of a lake, thinking about the woman he loves. He recalls the times they spent together and how she made him feel. He is hoping to see her again soon.
7. We’re Gonna Make It by The Staple Singers
The Staple Singers sing of hope and resilience in the face of adversity in “We’re Gonna Make It.” Despite the challenges they face, the group remains optimistic and believes that they will overcome whatever obstacles come their way. They encourage listeners to stay positive and keep fighting, because eventually things will get better.
8. I’ll Take You There by The Staple Singers
The song is about taking someone to a better place, free from all the troubles of the world. The singer assures the person that they will be safe and happy there.
9. Crook County by Speedknot Mobstaz, Twista
The song is about the harsh realities of living in Crook County, which is located on the south side of Chicago. It paints a picture of a place where violence is a way of life, and where drugs and gangs are rampant. The song also talks about the hope that exists in spite of the tough circumstances, and how people can make it out of Crook County if they are determined to do so.
10. Homecoming by Ye
“Homecoming” is a song by American rapper Ye about his return to his hometown after a long time away. The song is a reflection on his life and how it has changed since he left.
11. My Kind of Town by Frank Sinatra
The song is about a person who loves their hometown and is content living there. They don’t care about the fancy things in life, they just want to be surrounded by the people they love in a place that feels like home.
12. Lake Shore Drive by Aliotta Haynes Jeremiah
“Lake Shore Drive” is a song written by Aliotta Haynes Jeremiah and performed by Aliotta Haynes Jeremiah. The song is about a drive down Lake Shore Drive in Chicago.
13. Sweet Home Chicago by Robert Johnson
The song is a blues ballad about a man’s love for the city of Chicago. The man is homesick for the city and its people, and he sings about how much he misses it.
14. Via Chicago by Wilco
The song is about a man who is reflecting on his life and how it has changed since he left his hometown of Chicago. He is now living in New York City and is struggling to adjust to the fast-paced lifestyle. He misses the slower pace of life in Chicago and the people he left behind.
15. Have You Seen Her by The Chi-Lites
The song is a heart-wrenching ballad about a man who is desperately searching for the love of his life. He has lost all hope and can’t seem to find her anywhere. The lyrics are full of emotion and paint a picture of a man who is lost without the love of his life.
16. Love Train by The O’Jays
“Love Train” is a song by The O’Jays. It was released in 1972 as a single from the album Back Stabbers. The song was written by Kenny Gamble and Leon Huff. It peaked at number one on the US Billboard Hot 100 and number five on the UK Singles Chart.
17. Ribbon in the Sky by Stevie Wonder
The song is about a man who is looking up at the stars and dreaming about being with the woman he loves. He is hoping that someday they will be together again.
18. Sweet Home Chicago by The Blues Brothers
The song is about a man’s love for his city, Chicago. He talks about all the things he loves about the city, from the food to the people.
VI. Pop Songs About Chicago
1. If You Leave Me Now by Chicago
The song is about a man begging his lover not to leave him. He pleads with her to stay and promises that he will change and make things right. He is willing to do anything to keep her from leaving.
2. Make Me Smile by Chicago
The song is about a person who is struggling and feeling down, and how the person they love can make them smile again.
3. Color My World by Chicago
The song is about the simple pleasures in life and how they can make the world seem more vibrant. The singer reflects on how a loved one’s smile can color their world and make everything seem more beautiful. They express their gratitude for the small moments that make life worth living.
4. 25 or 6 to 4 by Chicago
The song is about a musician who is up all night trying to write a song. He is struggling to come up with the right words and is feeling frustrated. However, he eventually comes up with the perfect melody and lyrics.
5. Beginnings by Chicago
The song is about starting over and beginning again. It is about taking chances and making mistakes. It is about learning and growing.
VII. Rap Songs About Chicago
1. Homecoming by Ye
“Homecoming” is a song by American rapper Ye about his return to his hometown after a long time away. The song is a reflection on his life and how it has changed since he left.
2. Chicago by Michael Jackson
In the song, Jackson talks about his love for the city of Chicago and how it has helped him become the man he is today. He talks about the city’s skyline and how it has inspired him to reach for the stars. He also talks about the city’s people and how they have always been there for him.
3. I Ain’t Even on Yet by GLC
The song is about the rapper not being “on yet,” meaning he hasn’t reached his full potential. He talks about how he’s been grinding and working hard, but he knows he still has a long way to go. He’s not bragging or boasting about his success, but instead is motivating himself to keep going.
4. Po Pimp by Do Or Die
The song is about a pimp who is very successful at what he does. He has many women who work for him and he is very proud of his accomplishments. He is also very generous with his money and gives to those who are less fortunate.
5. Walk Wit Me by DA Smart
The song is about a young man who is trying to find his way in life and asking for guidance from a higher power. He is struggling with making the right choices and is looking for someone to walk with him on his journey.
6. Juice by Chance the Rapper
The song is about Chance the Rapper’s love for Juice, a girl he once knew. He talks about how he misses her and how she was the best thing that ever happened to him.
7. Da B Side by The Notorious B.I.G.
The song ‘Da B Side’ by The Notorious B.I.G. is about the rapper’s experiences with women in the music industry. He talks about how he has been able to sleep with many famous women and how they often throw themselves at him. He also talks about how he is not looking for a relationship and how he is just in it for the sex.
8. Still Po Pimpin’ by Do Or Die
Still Po Pimpin’ is a song about continuing to be a pimp despite the odds. The song talks about how pimping is a way of life and how it’s not easy to just stop. Despite the difficulties, the speaker in the song is determined to keep pimping because it’s what he knows best.
9. Wetter by Twista
The song is about a man who is trying to convince a woman to have sex with him. He talks about how the weather is perfect for it and how he is feeling.
10. Chicago Nigga by L.E.P Bogus Boys
The song is about the city of Chicago and how it is full of violence and crime. The song talks about how the city is full of “niggas” who are responsible for the crime and violence.
11. Why They Mad by Sasha Go Hard
The song is about Sasha Go Hard’s haters and why they are mad at her. She talks about how she is a boss and how she does not need anyone’s approval.
12. Overdose by Twista
The song is about a man who is addicted to a woman and cannot get enough of her. He compares his addiction to a drug addiction and describes how he is always thinking about her and how she makes him feel.
13. Chi-Town by Bump J
The song is about the city of Chicago and how it is full of violence and crime. Bump J is from the city and he talks about how he has seen people get killed and how there is always someone getting shot. He also talks about how the city is full of drugs and how he has seen people get addicted and how they end up losing their lives.
14. How We Chill by Molemen
The song is about how the Molemen chill and enjoy life. They are not concerned with the material things in life, but rather focus on having fun and enjoying the moment.
15. Move Around by Bump J
The song is about moving around and not being stagnant in life. It is about taking chances and making decisions that will lead to a better future.
16. OTF by Lil Durk
“OTF” is a song by American hip hop recording artist Lil Durk, released on March 11, 2016, as the first single from his second studio album, Lil Durk 2X. The song features production from C-Sick and assistance from Durk’s frequent collaborator and OTF label-mate, King Von. The song peaked at number 89 on the Billboard Hot 100.
The song is about the members of Durk’s OTF (Only the Family) crew, and how they are willing to die for one another. Durk pays tribute to his fallen comrades, and vows to never forget them. The song is full of street violence and drug references.
17. Kick, Push by Lupe Fiasco
The song is about a young boy who loves skateboarding. He is constantly pushed around by others, but he never gives up. One day, he finally learns how to kick and push himself, and he becomes a successful skateboarder.
18. Chi‐City by Common
“Chi-City” is a song by American rapper Common, released on February 7, 2005 as the lead single from his sixth album, Be (2005). The song, which was produced by Kanye West, features a sample of the 1971 song “I’m New Here” by Gil Scott-Heron. Common’s lyrics discuss his hometown of Chicago and its residents, as well as his own experience growing up in the city. The song received positive reviews from music critics, who praised its production and Common’s lyrics.
19. Stratford On Guy by Liz Phair
The song is about a woman who is in love with a man who is in love with someone else. She is trying to figure out what to do and how to tell him.
20. The Real Weight by No I.D.
The song is about a person who is struggling to keep up with the demands of life. They feel like they are carrying the weight of the world on their shoulders and they can’t keep up. The song is about the struggles of life and how sometimes it feels like you are carrying the weight of the world on your shoulders.
21. Fiesta by R. Kelly
Fiesta is a song by R. Kelly. It is about a party that is happening. There is a lot of excitement and energy in the song. Kelly encourages the listener to let loose and have a good time.
22. Funkdafied by Da Brat
The song is about a woman who is confident and proud of her sexuality. She is not afraid to flaunt her body or her skills in the bedroom. She is confident and knows what she wants.
23. Drivin’ Down the Block by Kidz in the Hall
The song is about a young man driving around his neighborhood, thinking about the girl he loves and how he can’t wait to see her again. He talks about how the city looks different at night, and how he feels like he’s the only one awake.
24. Sexy Lady by Hitmaka
This song is about a woman who is very attractive and the speaker is trying to woo her. He talks about how she makes him feel and how he wants to be with her. The song is very sexual in nature and describes the speaker’s physical desires for the woman.
25. Val Venis by King Louie
“Val Venis” is a song by American rapper King Louie. It was released on June 30, 2017, as a single from his album Tony 2. The song features production from frequent collaborator and fellow Chicago native, ChaseTheMoney.
26. Hip-Hop Saved My Life by Lupe Fiasco
The song is about how Lupe Fiasco was saved by hip-hop music when he was growing up in a tough neighborhood. He talks about how hip-hop was there for him when no one else was, and how it helped him stay out of trouble. He also talks about how hip-hop has helped other people in similar situations, and how it can be a force for good in the world.
27. Hay by Crucial Conflict
The song is about a group of friends who are trying to have a good time despite the struggles they face in their lives. They talk about the things they enjoy doing together, and how they support each other through thick and thin. Despite the hard times, they know that they can always count on each other.
28. Southside by Common
The song ‘Southside’ by Common is a tribute to the south side of Chicago, where the rapper grew up. He reflects on the tough times he’s faced in his life, but also the positive moments and people that have shaped him. Despite the challenges, he’s proud to be from the south side and grateful for everything it has taught him.
29. Here I Go by Infamous Syndicate
The song is about a person who is struggling with addiction and is trying to get clean. The person is telling their story about how they got into addiction and how it has ruined their life. They are trying to stay strong and not give up, but it is a struggle.
30. 65th & Ingleside by Chance the Rapper
“65th & Ingleside” is a song by American rapper Chance the Rapper. It was released on October 31, 2016, as the lead single from his third mixtape, Coloring Book (2016). The song features guest vocals from singer-songwriter Saba. The song was produced by Nate Fox, Peter Cottontale, and Francis Starlite of the band Francis and the Lights.
31. L’s Anthem by Lil Durk
L’s Anthem by Lil Durk is a song about the street life in Chicago. Durk talks about the struggles of growing up in the city and the violence that he has seen. He also talks about the people who have been killed in the city and how it has affected him.
32. Crook County by Speedknot Mobstaz, Twista
The song is about the harsh realities of living in Crook County, which is located on the south side of Chicago. It paints a picture of a place where violence is a way of life, and where drugs and gangs are rampant. The song also talks about the hope that exists in spite of the tough circumstances, and how people can make it out of Crook County if they are determined to do so.
33. On Ill by E.C. Illa
The song is about a person who is struggling with their mental health, and how they feel about it. They talk about how they feel like they’re not good enough, and how they’re constantly fighting against themselves. They talk about how they feel like they’re losing their mind, and how they’re scared of what they might do.
34. Love Sosa by Chief Keef
Love Sosa is a song by American rapper Chief Keef. It was released on October 18, 2012, as the lead single from his debut album Finally Rich. The song was produced by Young Chop. The song peaked at number 91 on the Billboard Hot 100.
35. Chicago Freestyle by Drake
The song is about a man who is from Chicago and is now living in Toronto. He is talking about how he misses his hometown and the people there.
36. Gettin’ Some by Shawnna
The song is about a woman who is attracted to a man who is already in a relationship. She is trying to convince herself that it is okay to go after him, even though she knows she is going to hurt the other woman.
37. Bitch Bad by Lupe Fiasco
In the song, Lupe Fiasco talks about how society looks down on women who are “bitchy” or “ghetto.” He argues that these women are often misunderstood and that they should be respected. He also talks about how men are often to blame for the way women are treated, and how they need to step up and be better role models.
38. Failure by Lupe Fiasco
The song is about how society tells people that they have to be a certain way in order to be successful, and how this pressure can lead to failure. Lupe Fiasco raps about how he has seen people around him succumb to this pressure, and how it has led to them making bad decisions and ultimately failing. He also talks about how he has been able to overcome these pressures himself, and how he is now successful because of it.
39. What You Be About? by E.C. Illa
The song is about a guy who is trying to figure out what his girlfriend is up to. He is asking her questions and she is not giving him any answers. He is getting frustrated and wants to know what she is up to.
40. Soul by the Pound by Common
The song is about the value of soul, or inner strength and integrity. Common raps about how soul is more valuable than money, and how it is the key to success in life. He encourages listeners to stay true to themselves and to never give up.
41. Hey Ma by Chance the Rapper
Hey Ma is a song about a young man who is in love with a girl who is in love with someone else. The young man is trying to tell the girl that he is the one for her and that she should forget about the other guy.
42. Angels by Chance the Rapper
The song is about a young man who is struggling with making ends meet. He turns to drug dealing in order to make some extra money. He is eventually caught by the police and is facing a long prison sentence. However, he is given a second chance when the judge offers him a chance to go to rehab instead. The young man is grateful for this opportunity and is determined to make the most of it.
43. I Don’t Like by Chief Keef
I Don’t Like is a song by Chief Keef. The song is about Keef’s disdain for people who don’t like him. He talks about how he doesn’t care about what they think and how they’re not worth his time.
44. Lookin Boy – Main Version by Hotstylz
The song is about a boy who is not very good looking, but who is confident in himself and his abilities. He is not afraid to approach girls and is always looking for a good time.
45. Freestyle or Written by Molemen
The song ‘Freestyle or Written’ by Molemen is a track that showcases the group’s rapping ability. The lyrics are written in a way that allows the rappers to show off their lyrical prowess, and the beat is catchy and will keep listeners hooked. The song is a great example of the group’s talent, and it is sure to please fans of their music.
46. 50 Years by All Natural
“50 Years” by All Natural is a song about a man who is looking back on his life and reflecting on all that he has accomplished. He talks about how he has worked hard all of his life and how he is proud of all that he has accomplished. He also talks about how he is looking forward to the next 50 years and what he hopes to accomplish in that time.
47. Chiraq by Chief Keef
The song is about the violence in Chicago, and how it is compared to the war-torn city of Iraq.
48. City To City by Al’tariq, Lil Ray, Grav
This song is about the city life and how it can be tough sometimes. The artists rap about how they have to hustle to make it in the city. They also talk about how the city can be dangerous and how they have to watch their back.
49. Black Mags by The Cool Kids
The song is about a group of kids who are into a street gang lifestyle. They are “black mags” which is a term for a specific type of street gang. The song talks about their lifestyle and how they are able to get away with things because they are in a gang.
50. Emotions by Twista
The song is about the emotions that come with a break-up. The first verse is about the hurt and pain that the person feels, and how they are trying to cope with it. The second verse is about how the person is trying to move on, but they still have feelings for their ex. The chorus is about how the person is trying to hide their emotions, but they keep coming back.
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