Last Updated on December 29, 2025 by Christian Adams
Chicago is my hometown. Born on the West Side and raised in the suburbs of DuPage County, I spent the first 30 years of my life in the Windy City, including a five-year stretch on the North Side (Bucktown). I miss my city every day. To be honest, I mostly miss the food and the people, not the weather.
Before You Start: 25 Songs About Chicago Edition
I’m assuming you’ve arrived at the post from a Google search and you haven’t read any of my other Songs About… listicles (e.g., Songs About California, Songs About New York, et. al.) There are two things you need to know.
- You’re gonna be disappointed if you came here expecting to see Frank Sinatra’s “My Kinda Town (Chicago Is)”.1
- My choices are not “the best” songs about Chicago. They’re songs I find strange, interesting, or representative of my hometown.
Super Bowl Shuffle – Chicago Bears Shufflin’ Crew
We are the Bears Shufflin’ Crew
Shufflin’ on down, doin’ it for you
We’re so bad we know we’re good
Blowin’ your mind like we knew we would
You know we’re just struttin’ for fun
Struttin’ our stuff for everyone
We’re not here to start no trouble
We’re just here to do the Super Bowl Shuffle
It’s difficult to articulate how much the 1985 Bears meant to the people of Chicago. The last major Chicago professional sports team to win a title before the Bears was the Chicago Blackhawks (hockey), who won the Stanley Cup in 1961. Twenty-four years of losing. A legacy of failure for the Cubs, White Sox, and Bulls fans, too. Fuckin’ losers across the board.
Chicago is a tremendous sports town, but much of our success happened long before you and I were born. Throughout the 1960s, ’70s, and into the ’80s, the Chicago Bears had one of the most miserable fanbases in the world. Our identity was wrapped up with the Bears, and we sucked. Many people blamed the Bears ownership, the McCaskey family, who seemed to care about everything except the Bears and their fans.
Finally, a miracle. One man, coach Mike Ditka, built one of the most dominant teams in NFL history. For many years, I could name every member of the Shufflin’ Crew and the position they played.
Forty years later, the Bears have been back to the Super Bowl once (in 2006), and they got destroyed by Payton Manning and the Indianapolis Colts. But it doesn’t matter. We were alive to see William “Refrigerator” Perry score a touchdown.
Chicago – Graham Nash
Though your brother’s bound and gagged
And they’ve chained him to a chair
Won’t you please come to Chicago
Just to sing
In a land that’s known as freedom
How can such a thing be fair
Won’t you please come to Chicago
For the help we can bring
We can change the world
Originally appearing on Nash’s 1971 solo debut album, Songs for Beginners, “Chicago” (aka “We Can Change the World”) was written as a response to the 1968 Democratic Convention protests and the legal battle of the Chicago Eight, a group of men arrested and charged with conspiracy to incite a riot.
In the lyrics, Nash specifically invites his fellow musicians to “come to Chicago” to perform at a fundraiser for the Chicago Eight. It was a pointed message to Neil Young and Stephen Stills regarding the proposed benefit concert. They never made it to the event, but the single went to #19 on the Billboard Hot 100.
Sweet Home Chicago – The Blues Brothers
Come on
Baby don’t you wanna go
Hi-de-hey
Baby dont you wanna go
Back to that same old place
Oh sweet home Chicago
Honest to goodness, I hate this fuckin’ song, but there was a brief window in the late 1970s when I loved the Blues Brothers.
People don’t believe me, but I never liked blues music. It’s incongruous. Chicago is “the home of the blues”, so to speak. I should like it.
As much as I don’t like it, “Sweet Home Chicago” is our theme song.
Chicago Bound – Jimmy Rogers
I didn’t need no steam heat by my bed
The little girl I had kept it cherry red
But I left that town
You know I left that town
When I left St. Louis you know I was Chicago bound
I’m gonna tell you something that you all should know
Chicago is the best place I ever know
I’m gonna stay in this town
I’m gonna live in this town
I’m gonna live in Chicago, it’s the greatest place around
If I’m gonna listen to the blues, it’s gonna be stuff like this, not the Blues Brothers or ZZ Top.
Saturday in the Park – Chicago
Saturday in the park
I think it was the Fourth of July
Saturday in the park
I think it was the Fourth of July
People dancing, people laughing
A man selling ice cream
Singing Italian songs
Bands named after cities, states, and countries sometimes have a song that namechecks their hometown (or moniker). For example, Boston has at least one song that mentions Boston (“Rock and Roll Band”). Chicago has a song called “Take Me Back to Chicago”, which stinks. “Saturday in the Park” is about Central Park in New York, so it’s misplaced on the list, but I’m not listening to “Take Me Back to Chicago” again. Pretend they’re singing about any one of a dozen major parks in Chicago. Pick one.
I might argue that every Chicago song is about the city of Chicago.
Lake Shore Drive – Aliotta Haynes Jeremiah
There’s a road I’d like to tell you about, lives in my hometown
Lake Shore Drive, the road is called and it’ll take you up or down
From rats on up to riches, fifteen minutes you can fly
Pretty blue lights along the way, help you right on by
And the blue lights shining with a heavenly grace, help you right on by
And there ain’t no road just like it
Anywhere I found
Running south on Lake Shore Drive heading into town
Just slippin’ on by on LSD, Friday night trouble bound
Chicago has a rich tradition of homegrown bands that could headline (and sell out) local venues like The Thirsty Whale and Park West, but didn’t make a dent in the national market. I’m talking about groups like Off Broadway, The Kind, Pezband, B’zz, The Insiders, The Effigies, Naked Raygun, et. al.
“Lake Shore Drive” was a modest regional hit played on late night classic rock radio after 2:00 a.m. It’s from the 1972 album of the same title. But I’m telling you, man, nobody knew Aliotta Haynes Jeremiah. They were the answer to an expert level trivia quiz. “Who wrote and performed the 1972 minor hit, “Lake Shore Drive”?
The song went global after being featured on the 2017 Guardians of the Galaxy, Vol. 2: Awesome Mix soundtrack.
The LSD reference is cheesy, but overall, it’s a vivid description of the most famous road in town and a nice bit of nostalgia for homers.
Born in Chicago – The Paul Butterfield Blues Band
I was born in Chicago, 1941
I was born in Chicago in 1941
Well, my father told me
“Son, you had better get a gun”
For the record, Paul Butterfield was born in Chicago, but he didn’t write the song, which is pretty gruesome if you listen closely.
Tonight, Tonight – Smashing Pumpkins
And the embers never fade
In your city by the lake
The place where you were born
Smashing Pumpkins have sold in excess of 30 million albums worldwide. Many people enjoy their music.
Borrowed Time – Styx
On borrowed time (On borrowed time)
Livin’ high (Whoohoo!)
Livin’ fine (Ahhh!)
Livin’ high
On Lake Shore Drive (Midnight ride)
If you remove “Babe” and “First Time” from Cornerstone (1979), it’s not a bad album. “Borrowed Time” isn’t about Chicago per se except the band was formed in Chicago, the album was recorded at Pumpkin Studios in Oak Lawn, and they namecheck Lake Shore Drive on the final chorus.
The Night Chicago Died – Paper Lace
Daddy was a cop on the east side of Chicago
Back in the USA, back in the bad old days
In the heat of a summer night
In the land of the dollar bill
When the town of Chicago died
And they talk about it still
A fictionalized account of a shootout involving Al Capone’s gang. I hated this song almost as much as the folk song, “There’ll Be a Hot Time in the Old Town Tonight“.
Late last night when we were all in bed
Mrs. O’Leary left her lantern in the shed
Well, the cow kicked it over, and this is what they said:
“There’ll be a hot time in the old town tonight!”
We used to mock the first line of “The Night Chicago Died” because there’s no east side of Chicago, jackass. Paper Lace was from Nottingham, England. They didn’t know any better.
In theory, Chicago is mainly divided into four sections: Downtown, North Side, West Side, and South Side. But even hardcore Chicago natives don’t know about East Side, one of the 77 official community areas of the city. Located on the far south side, between the Calumet River and the Illinois-Indiana state line, it’s 13 miles south of downtown Chicago.
Chicago – Sufjan Stevens
I fell in love again
All things go, all things go
Drove to Chicago
All things know, all things know
From Stevens’ chamber pop indie rock concept album, Illinois (2005). I’m hearing it for the first time today.
Dear Chicago – Ryan Adams
Nothing breathes here in the cold
Nothing moves or even smiles
I’ve been thinking some of suicide
But there’s bars out here for miles
I don’t know much about Ryan Adams’ music because the indie Americana genre is not my thing. What I’ve heard about Adams hasn’t been good. However, “Dear Chicago” is surprisingly evocative, and he’s right about one thing: bars are everywhere.
- As of October 15, 2025, there were 3,129 bars in Chicago.2
- Roughly 80 percent (or 2,500) are single-owner operations, while the remaining are part of larger brands.
- With 8–10 bars per square mile, Chicago has the fourth most bars per square mile in the U.S.3
- Only San Francisco, New York, and Boston have (slightly) higher densities.4
Peace Frog – The Doors
There’s blood in the streets, it’s up to my ankles
(She came) blood in the streets, it’s up to my knee
(She came) blood in the streets, the town of Chicago
(She came) blood on the rise, it’s following me
Just about the break of day
Another song about the 1968 Democratic National Convention, when Mayor RIchard Daley ordered his cops to squash the anti-Vietnam War protestors.
In the Ghetto – Elvis Presley
As the snow flies
On a cold and gray Chicago mornin’
A poor little baby child is born
In the ghetto
(In the ghetto)
“In the Ghetto” was written by Mac Davis and recorded by Elvis Presley in 1969 as a part of Presley’s comeback album, From Elvis in Memphis, and was also released as a single.
The question for Mac Davis, who was from Lubbock, Texas, and wrote the song while living in Atlanta, Georgia: Which ghetto are you talking about? We had several to choose from.
Via Chicago – Wilco
I printed my name on the back of a leaf
And I watched it float away
The hope I had in a notebook full of white, dry pages
Was all I tried to save
But the wind blew me back via Chicago
In the middle of the night
And all without fight
At the crush of veils and starlight
Wilco joins the Grateful Dead, Nick Cave & the Bad Seeds, and Deep Purple at the top of the list of artists that “I never got.” And I’ve given Wilco more chances to win me over than Tim Buckley, so, call it 20 attempts. I even tried to watch the documentary, I Am Trying to Break Your Heart (2002). Oops. That didn’t help.
Therefore, I apologize to all Wilco fans in advance for what I’m about to say. Country rock is unbearable (to me) unless it’s funny, like C.W. McCall’s “Convoy”. I don’t hear the genius of Tweedy’s songwriting at 84 beats per minute, regardless of the squeaky pedal steel parts. If anything, I’m envious of his success.
Mercy, sakes alive. Looks like we got us a convoy.
Except for two cheeky noise sections, “Via Chicago” sounds like every Bob Dylan record of the 1970s, especially Blood on the Tracks (1975), which everybody seems to love.
In fairness, I respect Jeff Tweedy and everybody involved in the band. They made the music they wanted to make. I think I’d like them if they didn’t take themselves and the music so seriously.
Lincoln Park Pirates – Steve Goodman
The streetlamps are on in Chicago tonight
And lovers are gazing at stars
The stores are all closing
And Daley is dosing and the fatman’s counting the cars
And there’s more cars than places to put ’em, he said
But I’ve got room for them all
So round ’em up boys
’cause I want some more toys
Hit the lot by the grocery store
Steve Goodman was massively influential at Chicago’s Old Town School of Folk Music, where he met, mentored, and later co-wrote songs with his friend, John Prine. This tune is about a predatory towing company on the North Side with cozy connections to Mayor Richard Daley, who ruled the city with corruption and intimidation.
Lincoln Park is Chicago’s “gold standard” North Side neighborhood. Named after the massive 1,200-acre park on the city’s lakefront. It is home to some of the city’s most expensive real estate, from historic Victorian brownstones to modern mansions.
In the 1970s, this neighborhood became the primary hunting ground for the Lincoln Park Towing Service. Because parking was (and still is) a nightmare, residents frequently found themselves at the mercy of towing companies that operated with aggressive, often borderline-illegal efficiency. Goodman found a specific irony in seeing wealthy, influential residents rendered completely powerless by a tow truck driver with a “hook.”
Every car owner in Chicago has been towed. If you haven’t been towed yet, just wait. You will.
Chicago X 12 – Rogue Wave
Gone are the good old days
Of painting young Courtney Pine
Listened to the taunts and the shouts
Of celebration wine
I never could make it work out right
Her milk glows in the blacklight
But it don’t matter
Because no one comes out to see us
Lake Michigan – Rogue Wave
Heaven is a switchboard that you want to fight
She would even miss you if you taught her sight
Power politician leaning to the right
Baby’s got a trust fund
That she’ll want to go off like that
Get off of my stack
Leave a little window
Get off of my stack
Rogue Wave was a pretty cool indie rock band from Oakland, California, so I don’t know why they’ve got two songs that reference Chicago on one album, Asleep at Heaven’s Gate (2007). However, I know:
- “Lake Michigan”, the first single from the album, was featured in a TV commercial for Microsoft’s second-generation Zune music players, and included on the OST5 of The Secret Life of Walter Mitty (2013) starring Ben Stiller.
- Courtney Pine is a British jazz musician and the principal founder of an influential jazz group, Jazz Warriors.
- The video for “Chicago x 12” was directed by Bob Odenkirk, a hometown hero from Berwyn via Naperville, Illinois. The song is also featured in the eighth season of Scrubs in the episode “Their Story II”.
When the Levee Breaks – Led Zeppelin
Oh, don’t it make you feel bad
When you’re trying to find your way home?
You don’t know which way to go
If you’re going down south
They got no work to do
If you’re going north to Chicago
It’s not impossible to estimate the number of times I’ve heard “When the Levee Breaks”, and I think it’s fun to try. Let’s do some Zeppelin math.
I’ve been alive for 20,787 days, and a Zeppelin fan for 17,137 days. For a period of 3,650 days, I probably listened to some form of Zeppelin every day. However, I can state confidently that I didn’t listen to any Zeppelin for 7,300 days. So, let’s round everything up and call it 10,000 days of listening to Led Zeppelin (or 27.3 years).
If you include the post-Bonham collection of outtakes, Coda (1982), the band released 81 original songs. I typically listened to entire albums in one sitting, with a preference for albums from Led Zeppelin II through Presence, but let’s also account for radio airplay and unintentional Zeppelin listening sessions when it was out of my control.
Statistical Analysis: Led Zeppelin Listening Simulation
| Album | Year | Song Count |
| Led Zeppelin I | 1969 | 9 |
| Led Zeppelin II | 1969 | 9 |
| Led Zeppelin III | 1970 | 10 |
| Led Zeppelin IV | 1971 | 8 |
| Houses of the Holy | 1973 | 8 |
| Physical Graffiti | 1975 | 15 |
| Presence | 1976 | 7 |
| In Through the Out Door | 1979 | 7 |
| Coda | 1982 | 9 |
| Total | 81 |
Building a probability analysis using both human and AI calculations, I came up with these results. After listening to Zeppelin at random for 10,000 days:
| Metric | Value |
| Daily probability of hearing “When the Levee Breaks” | 11.11% |
| Expected total plays | 1,111 times |
| Likely range (95% probability) | Between 1,048 and 1,174 times |
| Probability of 0 plays in 10k days | Approx 0 (essentially impossible) |
I think about that “going to Chicago” line almost every day.
A Guided Tour of Chicago – The Lawrence Arms
He’s Darren in front of 7-11 on Walton and State
She’s Babs up and down on Belmont right by the train
He’s Buddy and his wife in Uptown by the Aragon
He’s Andy selling Streetwise at the White Hen in Boys Town
I’d heard of these kids, but I’d never heard their music until today. They’re not my thing. But they namecheck Walton and State, Belmont Avenue, Uptown, the Aragon Ballroom, Streetwise, and White Hen…in four lines!
If you know White Hen Pantry, then you know Chicago.
Chicago – The Doobie Brothers
From the Doobie’s debut album (1971), produced by Ted Templeman, who signed Van Halen to Warner Bros.
Chicago – Michael Jackson
I met her on my way to Chicago
Where she was all alone and so was I
So I asked her for her name
She smiled and looked at me
I was surprised to see
That a woman like that was really into me
The Jackson family was from Gary, Indiana, which, at the time, was an extension of Chicagoland, and perhaps it remains. I dunno. But I was pretty fuckin’ surprised to learn that Michael wrote a song called “Chicago.” Turns out, he didn’t. The song was written by Cory Rooney and called “She Was Lovin’ Me”. Jackson retooled and recorded the track for his final studio album, Invincible (2001).
The track was not selected for Invincible and remained unreleased until 2010. Following Jackson’s death, Rooney revived the song for a posthumous release, but got nowhere. In 2014, the track was reworked yet again, this time by producer Timbaland. The Timbaland version of the track was ultimately included on Jackson’s second posthumous album, Xscape (2014), under the title “Chicago”.
Stratford-on-Guy – Liz Phair
I was flying into Chicago at night
Watching the lake turn the sky into blue-green smoke
The sun was setting to the left of the plane
And the cabin was filled with an unearthly glow
In 27-D, I was behind the wing
Watching landscape roll out like credits on a screen
I’d pay top dollar for a Liz Phair Christmas album. Top dollar.
Have You Seen Her – The Chi-Lites
Have you seen her
Tell me have you seen her
Oh, I hear her voice as the cold winds blow
In the sweet music on my radio
Another song that probably isn’t about Chicago per se, but the Chi-Lites were Chicago’s premier late 1960s to early 1970s R&B and soul group. They had had nearly 30 pop and R&B chart hits from 1969 until 1974.
Their major hits came in 1971 and 1972, “Have You Seen Her” and “Oh Girl”, the latter becoming a number one single on the Billboard Hot 100 in 1972.
Chicago – Tom Waits
The seeds are planted here
But they won’t grow
We won’t have to say goodbye
If we all go
Maybe things will be better in Chicago
Footnotes and Sources
- Frank Sinatra was probably a great guy who helped a lot of people during his life. He’s got more clout than Jesus. I just never liked Sinatra’s brand of mid-century scoobie-doobie music. I left him off the list of songs about New York, too, mainly because “New York, New York” is too obvious. And I think “My Kinda Town” is a shitty knock-off of “New York, New York”. ↩︎
- https://rentechdigital.com/smartscraper/business-report-details/united-states/illinois/list-of-bars-in-chicago ↩︎
- The 3,129 figure seems to be the most complete count of bars in Chicago currently available online — though it’s aggregated from business listing databases, not an official government registry. It encompasses a wide range of bar formats (standalone bars, lounges, etc.) and is updated as of late 2025. ↩︎
- This data is synthesized from Yelp Economic Research and City-Data reports. ↩︎
- Original soundtrack, sometimes called the original motion picture soundtrack. ↩︎
2 Comments
Pulaski at Night, Andrew Bird. Just the best.
That song was on the original list! But I listened a few times and really didn’t connect with it. I know Andrew Bird is a genius and everything. Just between you and me, I’ll probably sneak “Pulaski at Night” onto the list as an honorable mention or something.