28 Of The Best Songs About Chicago: Windy City Playlist

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It’s known as Chi-town, the Windy City, and Second City (even though it’s the country’s third-largest). So it should be no surprise, then, that Chicago has had hundreds of songs written about it or mentioned within it.

Performers in all genres, from blues and country to rock and rap, have featured the city’s landmarks, neighborhoods, and culture. Some are gritty and some are refined.

So take a tour of Lakeshore Drive in this list of the 28 best songs about Chicago of all time.

Related: Check out our list of the best songs about Illinois here.

1. “Bad, Bad, Leroy Brown” By Jim Croce

The first entry is a classic by folk singer-songwriter Jim Croce. His story is of a barroom fight between a gambling shark and bartender over one of the barmaids on “the southside of Chicago.” You’ll have to listen to find out who wins.

Croce, who was from Philadelphia, wrote several hit songs between 1966 and 1973. His life ended tragically when a single-engine plane he was in with five others hit a tree upon takeoff. He was just 30 years old.

“Bad, Bad, Leroy Brown” was a smash, reaching #1 on the Billboard Hot 100 list for two consecutive weeks in 1973, shortly before his untimely death.

2. “Back To Chicago” By Styx

Styx was the rock-and-roll brainchild of Dennis DeYoung, whose high baritone voice led a string of hit power ballads in the late 1970s and early 1980s.

The band hailed from Chicago, and one of their more successful albums Paradise Theater was built around a fading movie house in the city’s inner core.

In 1990, a reformulated Styx dropped an album called Edge of the Century. The final track was “Back to Chicago.”

Its lyrics tell of a love story between a singer on the road and a woman he has left behind. Soon, the band will be off the bus and back in the town his girlfriend lives in.

3. “Chicago” By Michael Jackson 

Five years after Michael Jackson’s death, an album called Xscape was released with previously unreleased tracks the singer had made between 1983 and 2001. In 2014, it debuted at #2 on the Billboard Hot 200 album chart.

“Chicago” was one of several songs Jackson recorded in 1999 but which the pop star decided against including on his hit album Invincible. 

The song is a mixture of ballad storytelling and up-tempo dancing about a passionate encounter with a beautiful Chicago girl. As he reflects on the night, and the favorable outcome, he can’t wait to see her again in the iconic city.

4. “Chicago (That Toddlin’ Town)” By Frank Sinatra

Originally published in 1922, it took about 35 years before Old Blue Eyes made “Chicago (That Toddlin’ Town),” the song by Fred Fisher, famous.

While toddling is a casual way of walking, in this case, the word refers to a style of jazz dance popular when the song was written.

Over the years, the song’s lyrics have been updated to reflect the city’s growing character. Some versions reference the Drake Hotel, Mrs. O’Leary’s cow, the Loop, and Marshall Field’s. Sinatra’s take was more classical, and he gave it his distinctive big-band croon.

5. “The Night Chicago Died” By Paper Lace

The next song on our list is a bit different. It’s by the British pop-rock band Paper Lace who wrote “The Night Chicago Died,” a song about a fictional shootout between Al Capone’s gang in the 1920s and the Chicago Police Department.

The song’s narrator is the son of a Chicago policeman who recounts the nervousness of his mother awaiting word of her husband’s fate on the night in question. Was he one of “about 100 cops” who died that night?

The song reached #1 on the Billboard Hot 100 list in 1974 and was later featured in season one of That 70s Show. Its opening synthesizer riff was meant to echo a police siren.

6. “Southside” By Common, Featuring Kanye West 

Common is the stage name for rapper and actor Lonnie Rashid Lynn. Underground for most of the 1990s, Common earned his first Grammy award in 2007 for “Southside.”

The song is about the working-class section of Chicago, and it mixes urban themes with the hopes of future wealth. 

A live version was performed with Kanye West just hours before the Chicago Bears made their last Super Bowl appearance.

Unfortunately, the Bears didn’t win that game, but you sure can’t blame Common for trying to inspire his hometown team.

7. “Leader Of The Band” By Dan Fogelberg

Dan Fogelberg wrote this simple and beautiful storytelling song as a tribute to his father, whose life as an itinerant musician left an indelible mark on him and his siblings.

Chicago gets referenced when he wonders how one of his brothers moved there after college.

Fogelberg has said that if he only had one song to write, this would be it. He was the only son to follow in his dad’s musical footsteps.

He, too, barnstormed the country playing gig after gig, showing how his father’s “blood runs through my soul.”  

8. “Dancing In The Street” By Martha And The Vandellas

This song is simply a great Motown classic. Marvin Gaye wrote it, and the Vandellas—a female trio led by Martha Reeves—took it to #2 on the Billboard Hot 100 list in 1964. Numerous artists have covered it over the years, including the Mamas and the Papas, Van Halen, and a Mick Jagger/David Bowie duet.

Among many cities to be mentioned, Chicago is one where infectious teenagers dance in the street to the new beats and music of their youth. It’s a joyful reminder of how music can unite everyone.

9. “All That Jazz” From The Musical Chicago 

The opening scene of one of Broadway’s most successful musicals of all time—and the Oscar-winning movie rendition—is the piano bar song that sets the stage for murder and mayhem.

“All That Jazz” starts nice and soft but then gets into the rhythm and blues section. Before you know it, the song is alive and kicking with great lyrics and a belter’s vocals. Add in some energetic dancing, and you have the quintessential scene-setter.

Chicago is now the longest-running revival on Broadway (nonstop since 1996) and you can clearly see and hear why with this song.

10. “City In A Garden” By Fall Out Boy 

Fall Out Boy formed in a Chicago suburb, and this song is their self-described love letter to the Windy City. Fittingly, at the end of a long tour, they got to play it live at Wrigley Field, the home of the Chicago Cubs.

Its chorus is an unabashed celebration of the city and runs throughout this three-and-a-half-minute ode to the hometown of their youth.

With an upbeat and electric vibe, it’s safe to say that it is a song worthy of becoming a city anthem. 

11. “In The Ghetto” By Elvis Presley 

The haunting song by the King of Rock and Roll, “In the Ghetto” was a comeback hit for Elvis. It peaked at #3 on the Billboard Hot 100 list in 1969 after Presley’s four-year absence on the charts.

This story centers on a young boy born in a Chicago ghetto to a single mother with too many kids already. He grows up poor and hungry and is killed after stealing a car as a teenager. As he dies, another boy is born “in the ghetto,” signifying that poverty and violence may be inescapable in the poorest sections of the city.

It doesn’t paint a rosy picture of Chicago, but it tells a sadly truthful tale that may be even more relevant now some 50 years later.

12. “Lido Shuffle” By Boz Scaggs 

There are two ways to look at the song “Lido Shuffle”. First, the protagonist is a down-and-out gambler looking to make one last killing before going straight. Or he’s a traveling musician who’s always one step behind.

In either case, Chicago (in this case, “Chi Town”) is a place everyone should be at least once before heading to the border. We assume that means Canada.

What we do know is this: Lido is a down-and-out loser who seems to miss opportunity after opportunity. He’s always looking for one more hustle before calling it quits.

13. “Only In Chicago” By Barry Manilow 

Barry Manilow may be better known for his “Weekend in New England,” but he also voiced this song as a tribute to Chicago’s better instincts.

Maurice White, of Earth, Wind, and Fire fame, wrote the lyrics and composed the music for this song. It appeared on his self-named solo album in 1980.

By then, Manilow was already a major star with a set of signature radio hits like “I Write the Songs” and “Mandy.”

This up-tempo funk song was largely overlooked, but the sentiment of a Chicago love affair reminds one of Lake Michigan, deep-dish pizza, and the Sears Tower.

14. “Stratford-On-Guy” By Liz Phair 

Another artist who grew up in the Second City, Liz Phair wrote this song about a traveler making it into Chicago on a nighttime plane bound for O’Hare International Airport.

Sitting behind the wing in seat 27-D, she’s wearing headphones, drinking a cocktail, and wondering what lies ahead.

It’s the 17th of 18 songs on Liz Phair’s debut album Exile In Guyville. Her combination of indie rock and low-fidelity recordings has garnered a spot in the top 100 of Rolling Stone Magazine’s list of the best albums of all time.

15. “65th And Ingleside” Ay Chance The Rapper 

His big sister bought a house on the streets mentioned in the title, and Chance the Rapper has said there was a lot of female energy in that house. He’s also lamented that he felt as if he didn’t belong unless he could help pay in some way.

The house in question was nothing to look at from the outside, but Chance remembers it as a beautiful home for all who lived there. Ultimately, Chance was able to repay the love and kindness many times over.

As he observes in the song, no mansions and bling can ever mean as much to him as the house on 65th and Ingleside.

16. “Born In Chicago” By Paul Butterfield

“Born in Chicago” is the opening number on the 1965 debut album for the Paul Butterfield Blues Band and has since become a blues standard.

Many artists have recorded the song including George Thorogood, Joe Louis Walker, and the late Tom Petty.

It’s another song whose lyrics may be more relevant now than five decades ago. Young friends die at the hand of gun violence. As politicians debate gun control legislation today, this song is a stark reminder of life on the tough streets of Chicago.

17. “Dear Chicago” By Ryan Adams 

Singer-songwriter Ryan Adams left the band Whiskeytown in 2000 to record his first solo adventure.

Among his early efforts is this ode to the chilly, almost arctic, winters of Chicago when the wind howls off Lake Michigan and the snowdrifts are high.

The song is likewise somber. The narrator mentions his battles with bipolar when the lows get him thinking of suicide—a real problem in the frigid winter months of the Midwest.

But there’s one bright spot as a girl reminds him of the city he loves.

18. “Lake Shore Drive” By Aliotta, Haynes, Jeremiah 

Locals know Lake Shore Drive in Chicago as LSD, but people outside the Windy City thought the rock trio that wrote and performed this song were talking about the hallucinogenic drug lysergic acid diethylamide.

In fact, one line in the song could be taken as a double entendre to mean both.

Either way, the tune brought the  Chicago-based rock group fame and fortune. “Lake Shore Drive” was recorded on New Year’s Eve 1971 and New Year’s Day 1972.

Over the years, they have updated the lyrics to reflect snowstorms and the holidays.

19. “Showtime In Chicago” By Joe Jackson 

British-born David Ian “Joe” Jackson had breakout success as a jazz-infused pop star in the mid to late 1980s.

In addition to some fancy pop songs, Jackson scored several movies including Tucker: The Man and His Dream in 1988.

One of his arrangements, “Showtime in Chicago,” landed on the soundtrack of the movie about Preston Tucker, a renegade car manufacturer in the 1940s who tried to go up against the Big Three automakers with disastrous results.

The song played under a scene where Tucker made a showing of his personally financed new automobile, the Tucker 48, in Chicago. Only 51 of the cars were ever produced.

20. “Take Me Back To Chicago” By Chicago 

It may have taken us a while, but we finally got around to listing a Chicago song from the Rock and Roll Hall of Fame band named after the city itself.

This title track on a 1985 compilation album was one of the last songs written by Danny Seraphine and David Wolinski. Soon, the band would hand over its songwriting duties to Peter Cetera.

It tells of the band’s ups and downs in Los Angeles, and how they longed for the more carefree lifestyle of their boyhood homes in Chicago.

There, they could sip a shake at the Tasty Freeze or listen to music in a less stressful atmosphere.

21. “Super Bowl Shuffle” By The 1985 Chicago Bears

The only Bears team to win the Super Bowl got a chance to show off its stuff when they performed this trite hit that immediately became a mainstream sensation.

Featuring players such as Jim McMahon, Walter Payton, Mike Singletary, and William “the Refrigerator” Perry, the song reached #41 on the Billboard charts.

Let’s be honest. It’s not the finest song dedicated to Chicago. But it was a phenomenon in its day and brought extra pride to the city after the team’s only championship of the Super Bowl era.

Not only that, more than $300,000 in song profits were donated to help needy families in the Windy City.

22. “Chicago Bound Blues” By Bessie Smith 

A great blues singer of the Jazz Age, Bessie Smith was one of the few African-American female artists to make it big in the early twentieth century. Her deep vocals inspired many jazz and blues singers that followed her.

This song is an ode to a city the Chattanooga-born contralto frequented in her busking days. At the time, she was restricted to black-owned theaters and music halls. Yet she still became the highest-paid entertainer of the time.

Sadly, Smith died in a car crash at only 43.

23. “I’m A Ramblin’ Man” By Waylon Jennings 

Country star Waylon Jennings may have sung this song of traveling around the country as survivor’s guilt. Jennings was supposed to be on the ill-fated small engine plane flight that killed Buddy Holly, The Big Bopper, and Richie Valens. However, he gave up his seat and lived to tell the tale.

On this track, he sings of various locales throughout the USA—West Virginia, California, New Orleans, and Alabama.

Of course, Chicago makes an appearance. In this song, Jennings reminds listeners not to get involved with any ramblin’ man. Otherwise, they might break their heart.

24. “Mrs. O’Leary’s Cow” By Brian Wilson 

Brian Wilson was the brains behind the Beach Boys. After a hiatus with the band, Wilson reemerged in 1966 with an instrumental composition called “The Elements,” which he had planned to be in four stages—Fire, Earth, Air, and Water.

His first effort was Fire, or “Mrs. O’Leary’s Cow.” It’s based on the three-day Great Chicago Fire of 1871 that destroyed 17,000 structures and left more than 100,000 people without homes.

Wilson begins the piece with slide whistles, and it goes off in different directions from there. This record won a Grammy award for Best Rock Instrumental Performance.

25. “Tonight, Tonight” By Smashing Pumpkins 

Another Chicago-based alternative rock band, Smashing Pumpkins had an international smash hit with this song that evocatively references their hometown as the “city by the lake.”

It went to the top of the Icelandic charts while reaching #2 in New Zealand, #7 in England, and #36 in the USA.

But the accompanying video is where “Tonight, Tonight” really shines. It received tremendous play on MTV (back when they aired music videos) and won six MTV awards in 1996, including Video of the Year.

Stylus magazine still ranks it #40 on its list of all-time best videos.

26. “Windy City” By Phish 

This might be the most interesting song on our list because Phish has only played it live once—in a concert at Toyota Park just outside Chicago.

About 30,000 lucky fans were in attendance that August 2009 day to hear it performed.

Otherwise, the studio version is the only official recording of it. The narrator is a couch potato who orders products from his television and references the snow Chicago all too often gets. 

27. “Jesus Just Left Chicago” By ZZ Top 

One of rock and roll’s mainstay acts for more than 50 years, ZZ Top was a three-man wrecking crew of blues and Southern-inspired hard-charging guitar rock that blew the doors off.

This 1973 hit begins with the title line and then tells how Jesus works his way from the Windy City through Mississippi, New Orleans, and California.

The vocals and guitar licks are seriously bluesy on this tune. Jesus turns “muddy waters” into wine before a healthy guitar duet takes center stage.

28. “Boogie Woogie Bugle Boy” By The Andrews Sisters

The final song on our list of Chicago songs goes back to the big band era. That’s when the Andrews Sisters released their classic doo-wop hit about a Chicago trumpeter who’s now playing reveille for the army’s Company B.

Their tight harmonies and infectious tempo make this song one that you’ll sing long after hearing it.

The Andrews Sisters earned an Academy Award nomination for the song, and it has been inducted into the Grammy Hall of Fame. Not a bad way to end our list.

Summing Up Our List Of Songs About Chicago

We’ve only scratched the surface of songs written about or mentioning Chicago.

But you can see there are tunes from just about every genre of popular music over the past 100 years that have drawn inspiration from the iconic Windy City.

Many of the artists mentioned above got their starts in and around Chicago. Others who haven’t still have plenty to write and sing about this extraordinary Midwest city. 

Do you have a favorite on this list, or is there a song you think is worth including?

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Written by Laura Macmillan
Laura has over 12 years experience teaching both classical and jazz saxophone and clarinet. She now resides in California where she works as a session and live performer.