The 15 Most 'Chicago' Songs Ever Recorded

While some songs may contain a quick reference or two to Chicago (“When the Levee Breaks”) or make you think about Chicago (“Chelsea Dagger”), some songs simply capture the essence of city from front to back. We've ranked the top 15 most 'Chicago' songs ever recorded weighing factors of local authenticity and overall quality -- apologies to Jim McMahon's rapping abilities -- and capped it off with an all-star Chicago Spotify playlist for your listening pleasure.

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Drive Thru Records/YouTube

15. “Somewhere on Fullerton” by Allister

Most Chicago line: “Somewhere down on Fullerton / There's a place that meant / So much to everybody like me.”
While Fall Out Boy shrieks out plenty of songs about Chicago, this lesser-known track by local punks Allister makes the cut due to its dedication to the Fireside Bowl, which today hosts bowling but used to serve as one of the nation’s top venues for up-and-coming punk and indie talent. When Fireside announced it would stop regularly hosting shows, Allister’s response pretty much sums it up: “But I'm still trying / Just to figure out why / This feels so wrong / When it felt so right.”

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Atlantic Records/YouTube

14. “Crook County” by Twista

Most Chicago line:“In the Chi / It's kill or be killed / Hussle or die / You gotsta take the pie / Momma didn't lie.”
West Side native Twista deserves style points for this grooveworthy take on “this county of crooks” that comes with this warning: “Don’t come to the Chi, it’s just risking your health.”

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13. “The El” by Rhett Miller

Most Chicago line: “Let's say you're in Chicago and you're rattling along on the El / Yeah and the one who rides beside you is a stranger to herself / Nobody knows her own heart / You might have been introduced but you drifted apart.”

You have to admire an artist who writes a song about public transit and even more so when that artist somehow manages to make the rolling petri dish on rails sound romantic. While Rhett Miller seems to always be penning songs of love and heartbreak, he earns bonus points for lyrics about making out and breaking up on the train... acts all of us unfortunately have been exposed to at some point or the other.

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Asian Man Records/YouTube

12. “A Guided Tour of Chicago” by The Lawrence Arms

Most Chicago line: “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 Boystown. He was Ed from the South Side who gave me cigarettes and hope at Walgreen’s on Belden and Clark where inspiration dies alone.”
Few songs pack in more references to Chicago than this lightning-paced track from local punk goofballs The Lawrence Arms. Any song that references Uptown, the Aragon, Streetwise, and Boystown (along with specific 7-11, White Hen and Walgreen’s locations) automatically makes this list. That’s just the rules.

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Wegawam Music Co./YouTube

11. “Pulaski at Night” by Andrew Bird

Most Chicago line:“I paint you a picture / Of Pulaski at night / Come back to Chicago / City of, city of light.”
This track by local singer/songwriter/glockenspiel impresario Andrew Bird drips with love of his hometown, with emotional lines about Pulaski Ave at night and plaintive pleas (perhaps to a lover) to come back to Chicago. Themes of returning to the city seem to be a mainstay in many songs about Chicago, not just this one.

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10. “Born in Chicago” by Paul Butterfield Blues Band

Most Chicago line:“I was born in Chicago, in nineteen and forty-one / I was born in Chicago, in nineteen and forty-one / Well my father told me, son you had better get a gun.”
Paul Butterfield Blues Band is quite probably the best blues band you’ve never heard of, and their 1965 song “Born In Chicago” could not be more relevant today. With lyrics that run though young friends who “went down” presumably to gun violence, the song could serve as a soundtrack to today’s gun violence debate. 

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9. “Chi-City” by Common feat. Kanye West

Most Chicago line:“And ya say Chi-City / We don't stop, naw, we don't quit.”
“Chi-Raq” may get more attention, but Common has been penning tunes about his beloved hometown long before anyone was familiar with Nicki Minaj or her backside. Common brings on producer Kanye West and DJ A-Trak for a star-studded collaboration whose lyrics are much more pointed than its laid-back grooves might otherwise indicate.

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Chess Records/YouTube

8. “Chicago Bound” by Jimmy Rogers

Most Chicago line: “I’m gonna tell you somethin’ 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.”

This old blues standard may not be as famous as “Sweet Home Chicago,” but it packs more love for the city in a tighter space by declaring it “the greatest place around.” The song was later popularized by Canned Heat and remains a more under-the-radar Chicago classic.

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7. “Via Chicago” by Wilco

Most Chicago line:“I'm coming home / I'm coming home / I’m coming home / Via Chicago.”
While this popular Wilco track isn’t littered with overt references to the band’s hometown, the emotional content of this Henry Miller murder-inspired ballad is clearly all about Chicago. The song was first performed live at legendary shuttered local venue Lounge Ax in 1998 and has even inspired the popular Wilco fan site

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6. “Chicago (We Can Change the World)” by Crosby, Stills & Nash

Most Chicago line:“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 that we can bring.”
One of the top protest songs in an era of protest songs is all about the ’68 convention and the hell unleashed on protesters in the streets of Chicago. It also makes heavy references to the subsequent trial of the Chicago 8, with Graham Nash dedicating the song to Mayor Daley. But the positive refrain of “We can change the world” is the song’s strongest element.

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Roc-A-Fella Records/YouTube

5. “Homecoming” by Kanye West

Most Chicago line:“If you don't know by now, I'm talking 'bout Chi-Town.”
No hip-hop song plays out more like an anthem for the city than this insanely listenable track by Chicago’s biggest egomaniac (sorry, Rahm.) If you think a song all about coming home to Chicago that name-checks fireworks on Lake Michigan might struggle to reach a wide audience, see the 50 million hits on YouTube.

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4. “Lake Shore Drive” by Aliotta Haynes Jeremiah

Most Chicago line:“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.”
Lake Shore Drive’s most famous song scored the one and only hit for local group Aliotta Haynes Jeremiah in the late ‘60s, largely due to the naughty wordplay of the highway’s initials with the era’s number one psychedelic drug of choice. Despite the band’s denial that lyrics like “slippin’ on by on LSD” had nothing to do with acid, the song likely would have been forgotten without it.

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Reprise Records/YouTube

3. “My Kind of Town (Chicago Is)” by Frank Sinatra

Most Chicago line: “The Wrigley Building, Chicago is / The Union Stockyard, Chicago is / One town that won't let you down / It's my kind of town.”
We're pretty much required to put this one on the list. Everyone’s heard the song. If not, ask your grandparents.

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Reprise Records/YouTube

2. “Chicago” by Fred Fisher (popularized by Frank Sinatra)

Most Chicago line:“Say, you'll have the time / The time of your life / Bring all your friends / Your kids and your wife to / Chicago, Chicago / My hometown.”
Yes, Frank Sinatra is quite possibly the cheesiest artist who ever lived (sorry, dad). But that doesn’t stop his popular rendition of the 1922 song about the greatness of “that toddling town” by obscure artist Fred Fisher from being one of the most well known songs about Chicago. Maybe Old Blue Eyes sang it while downing steaks with Sam Giancana at Twin Anchors. It could have happened.

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1. “Sweet Home Chicago” by Robert Johnson

Most Chicago line:“Oh baby don't you want to go / Back to the land of California / To my sweet home Chicago.”

No surprise here, “Sweet Home Chicago” is easily the most well known song about Chicago, despite the original 1936 rendition by Robert Johnson containing more references to California than Chicago. Some have theorized that the Cali references refer to California Ave, but the altered version that replaces the “Back to the land of California” line with “Back to that same old place” is the better known version thanks to bands like The Blues Brothers who helped popularize the song for the modern era. Hey, they were on a mission from God.

Honorable Mentions:

“Chicago” by Sufjan Stevens
“Chicago Seemed Tired Last Night” by The Hold Steady
“Chi-Town” by The Cribs
“Back to Chicago” by Styx
“Southside” by Common
“Welcome to Chicago” by Kill Hannah
“Chicago” by Portugal. The Man.
“Chicago at Night” by Spoon
“Chi-Raq” by Nicki Minaj
“Chicago Is So Two Years Ago” by Fall Out Boy
“Living In Chicago” by the Bee Gees
“LAX to O’Hare” by The Academy Is…
“Tonight, Tonight” by Smashing Pumpkins
“When the Levee Breaks” by Kansas Joe McCoy and Memphis Minnie (popularized by Led Zeppelin)
“In the Ghetto” by Elvis Presley
“We’re All Crazy in Chicago” by Jonathon Brandmeier
“Super Bowl Shuffle” by the Chicago Bears
“Go Cubs Go” by Steve Goodman
“Chelsea Dagger” by The Fratellis

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Jay Gentile is a Thrillist contributor and, like the Paul Butterfield song, was born in Chicago. Follow @innerviewmag.