To some, the Windy City is one of the best places in the world. To others, it’s a nice place. But unlike New York or LA, Chicago isn’t a place you hear many people complaining about.
Instead, many songs have come down the pike, extolling the virtues of the place as artists who grew up there reminisce and songwriters use it as a setting for their tales. With such great energy, it’s no surprise that Chicago has inspired so much creativity.
Here are 22 songs about Chicago. It’s not the definitive list, but it’s a good place to start.
1. “Take Me Back to Chicago” by Chicago
You simply can’t have a list of songs about Chicago without a song by Chicago. The fact that this Chicago song has Chicago in the title and is a great song on its own makes it the perfect song about Chicago to top a list of songs about Chicago. By the way, if you say “Chicago” a bunch of times, it stops having any meaning at all.
With their timeless horns and skillful songwriting, Chicago the band made hit after hit, and even today, after 50-plus years, they’re still touring. “Take Me Back to Chicago” remains one of their biggest hits.
2. “Homecoming” by Kanye West
Love him or hate him, most people have to admit that “Homecoming,” West’s ode to his hometown of Chicago, is a pretty incredible piece of music.
The guest appearance by Chris Martin (another musician for whom many people have strong feelings) brings a Martin-esque piano line to the chorus. Over West’s beat, it makes for an excellent combination.
West raps about Chicago, comparing it to the feelings one has about one’s first love. There’s no doubt where the man’s loyalties lie.
3. “Meet Me in Chicago” by Buddy Guy
Guy mentions all things Chicago, from Wrigley Field to the legendary wind to Al Capone in this tribute to the Second City. He sings about the city with a wistfulness that almost seems at odds with the driving blues riff he plays on the guitar.
With the rhythm section laying down a beat that’s almost zydeco, it’s a mishmash of elements that probably shouldn’t work, but it does. It really does.
Add Guy’s blistering guitar solo that comes screaming in at around the three-minute mark, and you’ve got a cool piece of music.
4. “Sweet Home Chicago” by Robert Johnson
As the universally recognized god of Delta blues, Robert Johnson left a giant legacy despite setting foot in a recording studio only twice in his life. Legend has it that Johnson sold his soul to the devil at a Delta crossroads in exchange for music, ability, or fame—the stakes vary depending on who’s telling the story.
“Sweet Home Chicago” may be the most widely known song about the city, but even when Johnson recorded it (he may have written it, but we’ll probably never know for sure), fame and fortune eluded him. He was a working musician, playing dances and on street corners.
Before dying a suspicious death, Johnson was a relative unknown. It wasn’t until years after his death that musicologists rediscovered his small but influential catalog, and now, he’s hailed as one of the progenitors of the blues.
“Sweet Home Chicago” is one of those standards that any blues player worth his salt knows and probably plays live at most gigs.
5. “My Kind of Town (Chicago Is)” by Frank Sinatra
Written for Sinatra to sing in his 1964 film Robin and the Seven Hoods, “My Kind of Town (Chicago Is)” doesn’t make any social commentary. It doesn’t make subtle nods to any underlying issues the city might have.
Instead, it’s a straight-up puff piece about how great Chicago is. Most people who visit the city end up agreeing with the sentiment, as Chicago is, in fact, a pretty great place.
It was a big enough hit that Sinatra recorded it two more times over the rest of his career. Even if you don’t recognize the title, it’s one of those songs that, when you hear it, you go, “Oh, yeah. I know that song.”
6. “Bad, Bad Leroy Brown” by Jim Croce
During his stint in the National Guard, Jim Croce met a man named Leroy Brown. The guy wasn’t from Chicago, but Croce kept the name in his head because he thought it might work well in a song.
He was right. The piece tells the story of a bruiser of a bully from the rough part of Chicago who finally picks a fight with the wrong guy and comes out of it much worse for the wear. The song hit number one in the summer of 1973, and Croce died in a plane crash less than three months later.
He had a posthumous number one with “Time in a Bottle,” which remains a song with staying power fifty years after its release, but “Bad, Bad Leroy Brown” stands as Croce’s signature song.
7. “Back to Chicago” by Styx
Released at the tail end of Styx’s 1980s run of superstardom, “Back to Chicago” was the B-side of the 1990 single “Show Me The Way.” The band had just reformed after splitting up with the departure of guitarist Tommy Shaw.
Dennis DeYoung led the new line-up in the more synthesizer-driven direction that he’d begun with 1983’s album “Kilroy Was Here.”
“Back to Chicago” echoes a common theme in songs about cities—I was in a place I loved with the girl of my dreams. Then, for some dumb reason, I left, thinking I’d find greener pastures, but boy, was I wrong. I sure hope she’ll take me back.
While the tune starts with a schmaltzy, melodramatic opening, it gives way to a driving, 80s-adjacent power ballad. It ends up being a fun listen, even though the only Chicago reference outside the city’s name is a passing mention of walking on Lake Shore Drive.
8. “Chicago (We Can Change the World)” by Crosby, Stills & Nash
Graham Nash wrote “Chicago (We Can Change the World)” for his solo album, but it quickly became a CSN song they performed for many years.
It’s a protest song, which is not surprising because:
- CSN was a pretty socially conscious group.
- It came out in 1971 when protest songs were everywhere.
- It’s about the violence at the Democratic National Convention in Chicago in 1968.
There are references to Bobby Seale and the Chicago Eight, and you can hear in the men’s voices the outrage many people felt about the state of the country and the world at the time.
9. “Dear Chicago” by Ryan Adams
The Chicago in this song represents a person, so when Adams sings “Dear Chicago,” he’s speaking to someone specific, perhaps an old flame. Through the song, he’s processing emotions and seems to be addressing the person in Chicago about a different person in New York.
It’s a sad song, even though Adams goes back and forth in his discussion of being sad or not, finally deciding that he won’t cry anymore.
This is a song about loss and indecision. While the narrator misses Chicago and the person the city represents, he doesn’t know what to do with the feelings.
10. “Chicago Bound” by Jimmy Rogers
The title track of the criminally little-known bluesman Jimmy Rogers’ 1970 album, “Chicago Bound” features a classic blues bassline and mean, mean harmonica work from Big Walter Horton.
The lyrics detail a rambling man moving north through Memphis and St. Louis until he finally arrives in Chicago, “the greatest place around,” where he plans to stay.
“Chicago Bound” isn’t a wholly original piece of music, as Rogers openly admitted to adapting it from Memphis Slim’s “Memphis Bound,” but that doesn’t take anything away from one of the more celebratory songs about Chicago.
11. “Born in Chicago” by Paul Butterfield Blues Band
Paul Butterfield took his harmonica and his love for the blues—particularly Chicago-style blues—and showed the world that a white man could actually play the form. The Paul Butterfield Blues Band greatly impacted the genre even though, like Jimmy Rogers, they’re not as well-known as they should be.
The song’s lyrics tell of friends “going down,” presumably in violent deaths. This presumption is backed up by Butterfield’s assertion near the song’s beginning when he sings that his father told him he had better get a gun.
This is the band that gave the world Elvin Bishop, so it’s not like PBBB remains a complete unknown.
12. “Boogie Woogie Bugle Boy” by The Andrews Sisters
Written for an Abbott and Costello war movie, “Boogie Woogie Bugle Boy” remains the Andrews Sisters’ enduring contribution to pop culture. Though it’s a fun, jump-blues piece of music, at its heart, it’s a piece of World War II propaganda. Here’s why.
A Chicago-based trumpet player gets drafted but is reduced to playing reveille in the morning. He’s bummed out about it until a superior officer recognizes the problems, hunts up some other musicians, and the bugler gets to play in his own style with a band.
The message to prospective soldiers was that you could be in the army and still be true to yourself and that the armed services were for everybody.
Did it work? Well, we won the war, so…
13. “Southside” by Common
Common welcomes fellow Chi-town son Kanye West on this ode to his hometown. With references to infamous Chicagoans like domestic terrorist Jeff Fort, which is something of an inside-baseball callout, Common extols the city while admitting that there are problems there like anywhere else.
The presence of West adds more credibility to the love letter to the city, though Common isn’t someone who needs help. Still, who’s going to turn down help from a rap superstar?
14. “Stratford-On-Guy” by Liz Phair
Indie darling Liz Phair is one of rock’s most distinctive voices, and “Stratford-On-Guy” is no exception. The “Guy” in the title references the 80s music scene in Chicago, which was pejoratively called Guyville by many.
The song’s title combines the birthplace of Shakespeare, Stratford-Upon-Avon, and Guyville. But it doesn’t take potshots at the boys’ club that Chicago’s late-20th-century music scene was. Instead, the narrator, on a plane to the Windy City, looks out over the world out her airplane window and realizes the majesty of nature.
She sings about how all the random stress and noise of life fell away, and she had this epiphany in the skies over the City of Big Shoulders.
15. “Via Chicago” by Wilco
Frontman Jeff Tweedy was suffering from migraines and an opiate addiction when “Via Chicago” came out in 1999’s Summerteeth and the lyrically opaque song seems to be about Tweedy struggling with parts of himself he doesn’t like very much.
The writings of Henry Miller may also inspire it, but again, its lyrics, on some level, approach the indecipherable.
Still, the recurring idea of getting back home via Chicago, the band’s hometown, resonates.
16. “Sidewalks of Chicago” by Merle Haggard
“Sidewalks of Chicago” isn’t exactly a love letter to the Windy City. Rather, it tells the story of a man who left his small-town home for the big city and encountered only hardship and failure.
He meets a woman, falls hard, and then loses her. He never fully recovers and must admit that he’s lying to his family and the folks back home who voted him Most Likely to Succeed. The address they have to send him letters to is a homeless shelter.
The narrator is broke and broken, wandering the Chicago sidewalks and questioning where he went wrong in life.
17. “Living in Chicago” by the Bee Gees
Barry Gibb and his brothers aren’t exactly renowned for their treacly ballads, but that doesn’t mean they’re not nice to listen to. “Living In Chicago” is far away from “Stayin’ Alive” or “Nights on Broadway,” but it still contains the group’s signature harmonies.
It paints a lonely picture of a man who finds himself isolated in Chicago, where it’s paradoxically his home but also the loneliest place in the world for him.
It’s not that band’s biggest hit, and the strings seem a little over-produced, but it’s a soothing piece of music.
18. “In the Ghetto” by Elvis Presley
Mac Davis wrote “In the Ghetto” for the King of Rock and Roll, and those two men seemed to be the only ones who believed in it. Presley’s label wasn’t crazy about it as a single, but he stood his ground because he wanted to sing more serious songs than much of his earlier work.
“In the Ghetto” is not a glowing recommendation for living in Chicago. It’s a ballad, meaning it tells a story about a poor kid born in a rough part of the city. His mom already has too many kids to support, so the boy grows up living a life of crime.
He’s inevitably killed due to his life choices, and at the song’s end, another baby is born in the same neighborhood under the same circumstances. It was a downer, but it was Elvis’ first number one hit in four years when it came out in 1969.
19. “Jesus Just Left Chicago” by ZZ Top
ZZ Top’s 1973 album Tres Hombres contained the band’s smash hit “La Grange” and this classic piece of blues. It’s not really about Chicago other than Jesus just left there, but it’s still a quintessential Chicago song.
Though never released as a single, its power couldn’t be stopped, and it was one of the band’s most popular songs, and they played it live as much as they did their charting hits.
Billy Gibbons’ screaming guitar and gritty voice make the song a hard-hitting piece of blues. Nobody has replicated that sound, but the song has been covered by the likes of Phish, Daughtry, and Hank, Jr.
20. “Only in Chicago” by Barry Manilow
Like Jesus in the last entry, the narrator of “Only in Chicago” has left the city. The problem is that once he and his girl left the city together, everything fell apart.
He bemoans the loss of the laughter and love in their relationship and implies that it was all there because of the city where they lived. After all, there was love and magic in the air in Chicago.
Released as the B-side to Manilow’s 1980 single “I Made It Through the Rain,” “Only in Chicago” couldn’t have been more different from its A-side. It’s upbeat with sad lyrics, while “I Made It Through the Rain” is a soulful ballad that sounds pretty sad but is actually about getting over some hard times.
21. “The Night Chicago Died” by Paper Lace
This number one hit for Paper Lace takes artistic license to the extreme. Ostensibly about the St. Valentine’s Day massacre—a shootout involving men loyal to Al Capone and Bugs Moran—the tale told is about violence between gangsters and police.
One hundred officers die in the song, though the real-life violence had no police involvement. Legend has it that the band sent the song to then-mayor Richard Daley, who hated it so much that he told them to jump into the Chicago River.
Since its 1974 release, “The Night Chicago Died” has developed a following outside of the US. Artists from Korea, Mexico, Finland, and Venezuela have covered it in the years since its release.
22. “Super Bowl Shuffle” by the Chicago Bears
No list of Chicago songs would be complete without this ridiculously self-serving and murderously catchy hit from an NFL team. The Bears of the 1980s were a cultural phenomenon led by the divisive and charismatic quarterback Jim McMahon.
The song made it to number 42 on the charts and was inexplicably nominated for a Grammy, though it lost to Prince’s “Kiss.” Somewhat surprisingly, after recording “Super Bowl Shuffle,” the Bears won the big game two months later.
Hearing Mike Singletary rap about how he’s been jammin’ is worth the price of admission.
Conclusion
Chicago is a great city that has inspired a lot of art. Some of that art exists in songs about the place, and then some other songs may not be art but certainly have a place in a discussion of songs about Chicago.
We had to leave some off the list, but did we include your favorite?
