20 Best Songs About Chicago

September 12, 2019

From rock and blues to rap and jazz, here are the best songs written about Chicago:

1. Sweet Home Chicago

By Robert Johnson (1936)

By the Blues Brothers (1980)

It’s a popular Chicago Blues anthem and has several versions, but the original is credited to Robert Johnson. The song is a favorite reference for most Chicagoans and was even performed in the Blues Brothers movie. What’s more, a rendition of the song was (partially) performed by President Barack Obama at the White House in 2012. The Obamas hosted the In Performance at the White House: Red, White, and Blues,” to celebrate music. The audience was serenaded by jazz greats like Buddy Guy and B.B. King, and President Obama joined them in singing the first verse of Sweet Home Chicago — it’s (partially) home to him too.

2. My Kind of Town (Chicago) by Frank Sinatra (1964)

This number was written for the 1964 musical Robin and the 7 Hoods starring Frank Sinatra who also did the vocals for the single. Written by Sammy Cahn and composed by Jimmy Van Heusen, the song was nominated for the 1964 Academy Award for Best Original Song and for a Grammy. My Kind of Town praises Chicago and its institutions.

3. Chicago by Graham Nash (1971)

This song is rife with political and social allusions. The lyrics call attention to the anti-Vietnam protests during the 1968 Democratic Convention in Chicago and the trial of the Chicago 8. The chorus goes, “We can change the world / Rearrange the world,” a line that applies to the world as much today as it did back then.

4. Lake Shore Drive by Aliotta Haynes Jeremiah (1971)

The song gained popularity for its innuendo-filled lyrics. The band took advantage of Lake Shore Drive’s initials and penned lines like, “Slippin on by on LSD”. They claimed it has nothing to do with acid, but this track was produced in the 60s, so we’ll take those claims with a pinch of salt.

5. Chi-City by Common feat. Kanye West (2005)

Common has been writing lyrics for and about Chicago for a while, but this collaboration with Kanye West is our favorite. Its grooves might be chilled-out, but its lyrics pack a punch.

6. Homecoming by Kanye West (2007)

It’s a love letter from the rapper to his hometown. His lyrics tell his story about growing up on the Southside, moving away, and his love for Chicago. It’s featured on West’s Graduation album and is one of our favorites on this list.

7. Meet Me in Chicago by Buddy Guy (2013)

Because what song list about Chicago is complete without the blues? These electric blues melodies capture the spirit and charm of Chicago in a way that only soul music can.

8. Born in Chicago by Paul Butterfield Blues Band (1965)

They were schooled in the same gritty Chicago bars as greats like Muddy Waters, Little Walter, and Howlin Wolf. The lyrics of Born in Chicago are rife with references to the city’s mob culture of the 1940s, but we love it for its groovy guitar riffs.

9. Chicago Bound by Jimmy Rogers (1970)

It’s not as famous as Sweet Home Chicago, but this old blues standard is a great example of classic Chicago Blues by one of the masters of the Chicago blues scene.

10. Take Me Back to Chicago by Chicago (1985)

Its lines are replete with references to the laid back life of the Midwest. The groove starts as romantic but then the horn section breaks in for the chorus and that’s when you realize that this worthy number by an iconic rock group.

11. Lake Shore Driving by Duran Duran (1988)

If you’re in Chicago, a drive along Lake Michigan is a must-do. The perfect soundtrack to that drive? Lake Shore by Duran Duran. This instrumental piece is replete with obscure synth sounds that the band is famous for.

12. Tonight, Tonight Smashing Pumpkins (1995)

The Smashing Pumpkins made some of the most epic music videos and Tonight, Tonight was frontman Billy Corgan’s ode to Chicago. Corgan grew up in the Windy City’s Elk Grove Village and reminisced about his hometown in lines like “the city by the lake.” The video is fantastic too!

13. A Guided Tour of Chicago by The Lawrence Arms (1999)

It would be criminal not to put this song on a list of songs about Chicago — it probably has the most references to the city on this list. It has references to Uptown, Aragon, Streetwise, and Boystown, as well as specific 7-11, White Hen and Walgreen’s locations — that’s as Chicago as it can get.

14. Via Chicago by Wilco (1999)

It inspired Wilco’s fan site called viachicago.org, and while the song doesn’t have obvious references to Chicago, it’s all about the city and is on this list because it sounds so good!

15. The El by Rhett Miller (2002)

Can a song about public transport and a petri dish sound upbeat? Rhett Miller made it happen with The El. This number tells the story of making out and then breaking up on Chicago’s El. It happens.

16. Somewhere on Fullerton by Allister (2002)

This song is about the Fireside Bowl, a bowling alley in Chicago that was made famous for hosting punk shows. You can feel the enthusiasm for having the venue which perfectly fits the punk culture’s do-it-yourself ethos. This true blue collar bowling alley (sans disco balls and tech distractions) is still open for business.

17. Chicago by Sufjan Stevens (2005)

The centerpiece of his album Illinois, this song boasts an ensemble of violins, trumpets, and choir singers, with stunning vocals from Stevens. The lyrics reference his visits to Chicago during his numerous cross-country road trips. Chicago is where he saw his first concert- and where he had some run-ins with the law.

18. Chicago by Tom Waits (2011)

This song about experiencing hard-luck and wishing for a better life is all too familiar in urban centers like Chicago. The music is rife with horns, harmonica, banjo, electric guitars, and Tom Waits’ guttural, melancholic voice.

19. The Night Chicago Died by Paper Lace (1974)

The lyrics tell the story of a fictional shoot-out between the Chicago police and Al Capone’s thugs. The singer alludes to his mother’s anxiety as she waited for his father, a policeman, to come home. The song was featured in the classic Chicago film High Fidelity (2000) and Season 1 of That 70s Show:

20. When the Levee Breaks

By Kansas Joe McCoy and Memphis Minnie (1929)

By Led Zeppelin (1971)

The original version was a blues version by duo Kansas Joe McCoy and Memphis Minnie. The song was written as an ode to the tragedy of the Great Mississippi Flood of 1927, but it also had themes of rebirth. The Zeppelin version that made this song famous was featured on their fourth album and had a new guitar riff by Jimmy Page and drumming by John Bonham. Critics called “When the Levee Breaks” the greatest achievement of Zeppelin’s fourth album, and we agree. While it is a tale of woe Down South, the promised land in the song is Chicago- and we like it like that!


Super Bowl Shuffle by the Chicago Bears

Back in the days of Walter Payton, Jim McMahon, and William “The Fridge” Perry, the Chicago Bears were the first sports team to have their own rap song. It was released two months before they won the Superbowl. It came into being when a die-hard fan and his cheerleader girlfriend decided to write, produce, and choreograph this song. The single became an instant phenomenon when it was released in 1985 — it was nominated for a grammy and reached #41 on the US Billboard Hot 100.

Go Cubs Go by Steve Goodman

Written by musician Steve Goodman – a lifelong Cubs fan, it is the official Cubs victory song. It reached #3 on the Billboard’s Bubbling Under Hot 100 Single chart after the Cubs won the 2016 World Series. It’s a great sing along fit for the best baseball stadium on Earth.


The above article was written for this Chicago blog hosted by the Carlton Inn MidwayMidway Airport’s Best Value Hotel. The blog is meant to educate and entertain. Management does not warrant the accuracy or completeness of the information on this website. Carlton Inn Midway may make changes to the content or policies at any time without prior notice. That which was written above does not represent the voice of hotel management. Rather, it is the lone voice of the writer.