Chicago is a city that is full of life, culture, and history. It’s no wonder that so many artists have written songs about it! Whether you’re a Chicago native or just visiting for the first time, these 10 songs will make you fall in love with the city.

From soulful ballads to upbeat anthems, these tunes will have you feeling like a local in no time. So grab your headphones and get ready to explore all that Chicago has to offer!

Table of Contents

65th And Ingleside By Chance The Rapper.

This song, which features piano accompaniment and Chance The Rapper’s signature rap flow, is an ode to the city of Chicago. He speaks of his time growing up in the city and how much it means to him: “I got my start on 65th and Ingleside, I’m from the city where they don’t let no dreams die.”

The song pays tribute to the Windy City by name-dropping some famous areas, including Wrigley Field and Navy Pier.

It also features a big shout-out to Chance’s hometown of West Chatham—a neighborhood on the Southside of Chicago that he says “raised me right.

A Guided Tour of Chicago by The Lawrence Arms.

Lyrics like, “There’s that giant clock tower in the sky, with neon lights and a glowing cityscape” give listeners an intimate glimpse into the Windy City.

It even features shout-outs to some of Chicago’s iconic landmarks, including “the Picasso sculpture at Daley Plaza” and “Lake Shore Drive, and all that it provides”.

This song is the perfect soundtrack for a Chicago tour, and it paints a vivid picture of the city in its verses.

All That Jazz From The Musical Chicago.

Written by Fred Ebb and John Kander in 1975, the song was originally a part of the musical and featured on stage as one of its opening numbers.

The song is an anthem to the city of Chicago, praising it for its nightlife and culture while still acknowledging some of its more seedy sides such as crime and corruption.

It’s a perfect way to introduce the audience to the setting of the musical and get them in the mood for what’s to come. It also serves as a reminder that behind all its glamour and glitter, Chicago can be a dangerous place if you’re not careful.

The song has been covered by everyone from Frank Sinatra to Cyndi Lauper and continues to be an iconic part of Chicago’s musical legacy. This is one song about the Windy City that you won’t want to miss!

Back To Chicago By Styx.

This classic rock song is all about the city of Chicago, and it captures the feeling of longing for home that many people feel when living away.

The lyrics tell the story of someone who has left their hometown to pursue their dreams but finds themselves missing the familiarity they left behind.

From big-city lights to the wind off Lake Michigan, this song celebrates all that makes Chicago so special. It is a great reminder of why the city is such an incredible place to call home.

Bad, Bad, Leroy Brown By Jim Croce.

Released in 1973, this song tells the story of a “real cool cat” from the Windy City. The lyrics describe him as “the baddest cat in town” and he makes his moves on the South Side.

Although some of the details are exaggerated for dramatic effect, it paints an entertaining and iconic picture of life in the city.

The song has become a staple in Chicago clubs and bars, with locals singing along to its catchy chorus each time it’s played. It captures the spirit of the city and gives people an anthem they can proudly sing along to.

Boogie Woogie Bugle Boy By The Andrews Sisters.

Released in 1941, this classic song is based on a real-life incident at the Drake Hotel in Chicago. The band was playing “Boogie Woogie Bugle Boy Of Company B” when a floor show dancer began twirling and singing along to it.

The Andrews Sisters heard her performance and decided to record their own version with her as part of their act.

It went on to become one of the most beloved songs about Chicago and has been performed countless times by musicians around the world.

Born In Chicago By Paul Butterfield.

“Born in Chicago” is a blues song written by Nick Gravenites and Paul Butterfield for the Paul Butterfield Blues Band’s debut album.

The song tells of the struggles of an African-American man from the South Side of Chicago, and it highlights the raw emotion and rawness of life in The Windy City.

It is one of the most enduring blues songs about Chicago and remains a favorite among fans of the genre.

The song has been covered by numerous artists including Cream, Canned Heat, and Willie Dixon. It is one of the few blues standards that almost all blues musicians know.

Chelsea Dagger by The Fratellis.

This 2006 release is an anthem to the city of Chicago. With its infectious chorus, it has become a popular tune at sporting events throughout Windy City.

The song celebrates the city and gives a shout-out to “the boys in blue” – referring to the Chicago police force. It also name-drops many famous landmarks such as Wrigley Field and Wabash Street.

A great tune to get everyone in the city singing along, Chelsea Dagger is a classic example of a song about Chicago.

Chicago (That Toddlin’ Town) By Frank Sinatra.

This classic is one of the most popular songs about Chicago. It was written by Fred Fisher and first released in 1924 when it quickly became a popular hit, as well as an unofficial anthem for the city.

The song celebrates Chicago’s unique jazz style and its history as a major center of commerce and industry.

With lyrics like “You walk down Randolph Street and you see a sight to behold”, the song paints a vivid picture of what life was like in Chicago during that era.

Sinatra’s version of the song is instantly recognizable, with his smooth crooning making it the perfect background music for any trip to the city.

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

Released in 1977, this classic rock anthem honors Chicago’s long and rich history. The lyrics describe the city as a “city of broad shoulders,” referring to its industrial roots and the spirit of hard work that many of its citizens embody.

It also mentions a variety of landmarks throughout the Windy City such as Navy Pier, Lake Michigan, and the Field Museum.

Chicago At Night by Spoon.

This dreamy song takes listeners on a night-time journey across the city as they explore its sights and sounds.

The lyrics make references to many iconic places, such as Wrigley Field and Navy Pier, while painting a picture of the beautiful skyline that can be seen from the lakefront.

With its slow tempo and introspective lyrics, this song captures the peacefulness of Chicago in the evening and provides a sense of calm to those who listen.

Chicago Bound Blues By Bessie Smith.

Released in 1927, this classic blues song is a compelling story about the journey of a woman heading to the Windy City. She meets some interesting characters along the way, such as a hobo and “Mysterious Rider” who warns her not to go to Chicago.

Despite these warnings, Bessie Smith’s character perseveres and eventually reaches her destination. The song speaks to the ever-present lure of the city and the idea of taking risks in life.

Chicago Bound by Jimmy Rogers.

This classic blues song was written by Rogers in 1950 and released one year later. It’s an upbeat tune that celebrates Chicago and its many charms, from hot days to cold nights, from the Sears Tower to the lakefront.

The lyrics capture a traveler’s excitement at finally reaching his destination: “Oh momma, I’m so happy about what I’m gonna see, when I get to Chicago, that great big city.” The song has been covered by a number of artists over the years, including Muddy Waters.

Chicago by Fred Fisher (popularized by Frank Sinatra).

This classic song about Chicago highlights the city’s most iconic sights and sounds. From references to Navy Pier and Lake Michigan, to the hustle and bustle of downtown streets, this song paints a vibrant picture of life in The Windy City.

Chicago By Michael Jackson.

This classic song by the King of Pop is a tribute to the Windy City. The upbeat tempo and soulful lyrics commemorate Chicago’s landmarks, culture, and famous architecture.

From legendary blues guitarist Willie Dixon’s “Back Door Man” to Michael Jackson’s hit single, this song celebrates everything that makes Chicago great.

Though it was written as an homage to the city, it has also become an anthem of sorts – played at sports stadiums, festivals and concerts. It’s a great way to embrace the spirit of Chicago and show your love for this amazing town.

Chicago by Sufjan Stevens.

This song is an ode to the city of Chicago, recounting some of its history and honoring the people who have lived there.

The lyrics paint a vivid picture of the city with references to various landmarks, such as the Art Institute, Magnificent Mile, Lake Michigan and many more.

Stevens’ upbeat tempo and his heartfelt vocal performance make this song an inspiring tribute to the Windy City.

Chicago Morning by Chris Rea.

This song speaks of the beauty and magic found in the morning in the city. Rea sings about the bustling streets, tall buildings and people walking along the shoreline as they start their day.

He also praises Chicago’s skyline and its diverse cultures that make it such a vibrant place to be. The chorus of “Chicago Morning” is a powerful anthem of the city, singing “Oh, Chicago morning/A beautiful sight to see/From Lake Michigan all around me/A new day’s just begun in this city.”

This is a perfect song for anyone who has ever experienced the beauty of a Chicago morning and loves the city with all their heart.

Chi-City by Common feat. Kanye West.

This classic hip-hop track from the early 2000s captures the soul of Chicago. Common and Kanye trade verses about their hometown, rapping about its beauty, struggles, and resilience.

It’s a great introduction to the city for those who have never been or are just looking for an anthem that represents it. The chorus is unforgettable: “Chi-City, Chi-City. It’s in our blood and that’s why we win.”

City In A Garden By Fall Out Boy.

This song stems from heartfelt nostalgia for the city of Chicago and the band’s hometown. It’s a love letter to their birthplace, praising its beauty and diversity. The lyrics paint a nurturing picture of an oasis-like landscape that offers refuge and solace amidst chaotic times.

The chorus features singer Patrick Stump claiming “Chicago, it’s a city in a garden” – a fitting tribute to the Windy City and its many green spaces.

The song is an example of how art can be used to express admiration for one’s hometown, no matter where it may be. As Fall Out Boy sings, Chicago is “our place of peace, our saving grace”.

Crook County by Twista.

This song highlights the troubling reality of growing up in Chicago’s rural suburbs. In the song, Twista paints a vivid picture of his hometown and the difficulties he faced while coming of age in this environment.

He raps about poverty, gang violence, and drug addiction—all issues that plague many communities across Chicago.

Although it is an honest look at the harshness of life in some parts of the city, it is also a reminder to stay hopeful and have faith in oneself.

This song serves as an important anthem for many young people living in Chicago’s rural suburbs.

Dancing In The Street By Martha And The Vandellas.

This classic Motown tune is all about the joys of celebrating summer in Chicago. The lyrics talk about how people from all over are coming to dance, unify and have a good time in the city.

It serves as an ode to the beauty and spirit of Chicago that has been passed down through generations. Framed by horns, a catchy bassline, and soulful vocals, this song is the perfect representation of Chicago’s spirit.

Dear Chicago By Ryan Adams.

As the title suggests, this song is a tribute to Chicago and its people. The lyrics of the song are filled with emotion, describing a deep reverence for the city that Adams has experienced throughout his travels.

He paints a vivid picture of its lights, sounds and culture while also expressing his admiration for its inhabitants.

The chorus includes the lines; “To the people of Chicago, I’ll never forget you/ You’ve always been so kind to me and true”. It is a captivating song that captures the essence of this great city.

Homecoming by Kanye West.

Released in 2008, the song is an ode to the city of Chicago. The track features Kanye’s signature production style, with a heavy-hitting beat and samples of classic soul songs by Chaka Khan and Marvin Gaye.

In the song, Kanye reminisces on his childhood in Chicago, and how it shaped him into who he is today. He also pays homage to several local landmarks, including the South Side’s basketball courts and the Chicago Bulls.

The track is one of Kanye’s most beloved songs, and it has become an anthem for residents of Windy City.

I’m A Ramblin’ Man By Waylon Jennings.

Released in 1972, this song is a tribute to Chicago, the “Windy City.” It references some of Chicago’s iconic architecture and landmarks such as the El train, Navy Pier, and Wrigley Field.

Waylon Jennings sings about his appreciation for Chicago: “When I’m sad that I can’t go roam, I’m a rambling man but Chicago is my home.”

In The Ghetto By Elvis Presley.

This timeless classic from the King of Rock and Roll is an anthem to the struggles of the city’s South Side. Elvis croons about a young man born into poverty, trying to make it in the tough streets of Chicago.

It’s an emotional yet uplifting ballad that speaks to the power of resilience in even the direst situations.

Jesus Just Left Chicago By ZZ Top.

This classic rock song is a tribute to the city of Chicago and its many interesting sights. The lyrics talk about some of the most famous spots like the Navy Pier and Jackson Park, while also giving nods to some of the lesser-known attractions like the Baha’i Temple.

ZZ Top’s bluesy guitar riffs add an element of soul to the song, making it a great way to express one’s love for Chicago.

Lake Shore Drive By Aliotta Haynes Jeremiah.

This classic tune is an ode to Chicago’s beautiful Lake Shore Drive. The song was released in 1971 and has been embraced ever since as a nostalgic anthem for the city.

The lyrics detail a joyride on Lake Shore Drive, featuring mentions of many of the landmarks along its course.

From Belmont Harbor to Navy Pier, this song perfectly encapsulates the spirit of the Windy City. The song is a must-have for any Chicago music collection, so get ready to take a ride!

Leader Of The Band By Dan Fogelberg.

Dan Fogelberg wrote this song as a tribute to his father, Lawrence Fogelberg, who was a music teacher and leader of an Illinois band.

The song speaks of the love Dan had for his father and the pride he felt in him. It has become one of the most recognizable songs about Chicago, with its melancholy lyrics and memorable melody.

Lido Shuffle By Boz Scaggs.

Released in 1976, this song is all about Chicago. It’s a classic rock hit that has been covered by several other artists throughout the years.

The lyrics tell the story of someone who is “lucky enough to get away” and move from Chicago to Los Angeles. He reflects on his former life in Chicago and the things he misses about it.

Meet Me In Chicago by Buddy Guy.

This blues classic was released in 1959 and has since become one of the most iconic songs about Chicago.

It captures the hustle and bustle of the city, with lyrics like “Let’s meet in old Chicago/There’s a place I know where we can go/A place that never sleeps/Where everyone gathers to hear the blues.”

Buddy Guy has a deep connection to the city and is one of its most beloved musical personalities.

He’s performed countless times at venues throughout the city, and his live shows are always special occasions for fans. This song serves as a reminder of all the amazing music that Chicago has to offer.

Mrs. O’Leary’s Cow By Brian Wilson.

This song tells the story of Mrs. O’Leary and her cow, who is famously attributed to starting the Great Chicago Fire of 1871. Brian Wilson pays tribute to the city of Chicago in this track, describing the fire and its aftermath as he remembers this major event in the city’s history.

The melody has a country feel that perfectly captures the spirit of this story, giving it a unique and memorable sound.

The lyrics to the song also contain references to other landmarks in the city, including The Loop, Navy Pier, and Wrigley Field.

All of these elements come together to create an unforgettable track that truly captures the essence of Chicago.

My Kind Of Town By Frank Sinatra.

This classic ballad was written by Sammy Cahn and Jimmy Van Heusen, and released in 1964.

The song celebrates the city of Chicago, with Sinatra crooning lines like “My kind of town/Chicago is/My kind of people too” and “That toddlin’ town/Chicago is/It’s my home sweet home.”

The song has been used in countless movies and television shows, cementing itself as one of the most iconic songs about Chicago ever written.

Only In Chicago By Barry Manilow.

This song, released in 1973 and written by Barry Manilow, is a nostalgic ode to the Windy City. The lyrics tell the story of an immigrant who immigrated to Chicago from a far-away land, and all of the things he loves about it—from its old-time music that makes him “want to dance,” to its hot dogs that make him “smile with glee.”

Manilow paints a picture of the city as a deep and rich culture, one with deep roots in both music and food.

The song is an uplifting reminder of why Chicago is still loved by so many around the world—its vibrant culture and the people who make it so special.

Pulaski at Night by Andrew Bird.

This song is a beautiful tribute to the city of Chicago and its people. The song speaks of the winding road that follows along Pulaski, a highway that runs through Chicago’s Northwest Side.

Bird paints a picture of the city at night, describing how it looks from his view “as headlights fly like silver arrows in the moonlight”.

He talks about how the city has been “repaved and rearranged” but still maintains its unique character.

The song also mentions some of Chicago’s beloved landmarks such as Wrigley Field and the Sears Tower, which is now known as the Willis Tower. This nostalgic, melancholy track serves as a reminder to always appreciate where you come from, no matter how much it changes.

Showtime In Chicago By Joe Jackson.

Joe Jackson’s Showtime In Chicago is a rock/pop song about his experiences living and touring in the Windy City. The track was released on Jackson’s 1982 album Night And Day II, which featured some of his biggest hits such as Steppin’ Out, Breaking Us In Two and Real Men.

Showtime In Chicago paints a vivid picture of Jackson’s life in the city, from taking a train to walking down the Magnificent Mile. The song is full of energy and optimism, highlighting the beauty and potential of life in one of America’s greatest cities.

While mentioning some of Chicago’s iconic landmarks such as Lake Michigan and Marshall Field’s department store, Jackson questions why he ever left the city in the chorus.

The song has become a beloved classic in Chicago, with many locals singing along whenever it comes up on the radio or at concerts. It is an ode to the city and all its inhabitants, showing that no matter where you go, Chicago will always have a special place in your heart.

Sirius (Chicago Bulls Theme Song) by The Alan Parsons Project.

A tribute to the Chicago Bulls, this upbeat tune was written in 1986. It opens with a fast-paced beat and horn section before transitioning into a signature rock guitar solo.

The track includes lyrics that pay homage to some of the most beloved players in Bulls history, like Michael Jordan and Scottie Pippen. It has become synonymous with the city of Chicago, and is an integral part of the team’s history.

Somewhere on Fullerton by Allister.

2004 hit single paints a classic picture of Chicago through the eyes of an out-of-towner. The song captures the sights, sounds, and energy that make Chicago such a unique city.

From echoing el trains to massive skyscrapers, Everywhere on Fullerton gives listeners an intimate glimpse of the Windy City.

There’s even a mention of the city’s famous deep-dish pizza! This song is sure to evoke a sense of nostalgia for anyone who calls Chicago home. Country Grammar by Nelly.

Southside By Common Ft. Kanye West.

Southside is a hip-hop song by rapper Common and record producer Kanye West. It was released on October 19, 2005 as the lead single from Common’s sixth studio album Be (2005).

The South Side of Chicago serves as the backdrop for this track which pays homage to their hometowns. The song features references to several landmarks in the city including Wrigley Field and the Art Institute of Chicago.

Common raps about his childhood memories growing up in the south side of Chicago while Kanye provides an intense hook that speaks to their love for the city.

The song is a tribute to all those who are from or have been touched by the south side of Chicago, highlighting both its positive and negative aspects.

Stratford-On-Guy By Liz Phair.

This alternative rock song is about Liz Phair’s childhood memories of her hometown in Chicago. The catchy chorus includes the line “Chicago, my hometown” and lyrics that take listeners on a trip through the city’s various neighborhoods.

The song celebrates the spirit of Chicago and its diverse cultures, which are described with wistful nostalgia. The song peaked at number 44 on the US Billboard Hot 100 chart in 2003. It also earned Liz Phair a Grammy nomination for Best Female Rock Vocal Performance in 2004.

Sunshine in Chicago by Sun Kil Moon.

This song is a tribute to the city of Chicago and its people. It’s an upbeat track full of optimism, as lead singer Mark Kozelek sings: “Oh, be brave and take life by the hand / Love your city it’s nothing like Hail Mary Chicago land.”

The song celebrates all that makes Chicago unique — from its architecture to its people — and recognizes the struggles that come with living in a big city. With its infectious chorus, “Sunshine in Chicago” will remind listeners why they love the Windy City.

Super Bowl Shuffle By The 1985 Chicago Bears.

This song is often considered one of the most iconic songs to come out of Chicago. Released in 1985, it was written and performed by the members of the championship-winning Super Bowl XX team consisting of Walter Payton, Jim McMahon, and William Perry.

The track offers a unique look at the personalities of this legendary squad and their quest for gridiron glory. It’s a classic that will never get old.

Sweet Home Chicago by Robert Johnson.

It was written in 1936 and has become a classic blues song about the city. It is often performed by the American rock band The Blues Brothers, who made the song popular with their renditions of it on Saturday Night Live in 1978.

Take Me Back To Chicago By Chicago.

This song is classic Chicago and its music video shows off the city’s iconic skyline. It was released in 1982 on their album “Chicago 16” and has since become a fan favorite.

The lyrics describe a heartwarming longing to go back home: “Take me back to Chicago, where I can see my friends/Where the lake is like a shining sea/Oh how I’d love to be free, once again.”

The song paints a vivid picture of the people and places that make Chicago so special.

The El by Rhett Miller.

This upbeat, uptempo song captures the feeling of a Chicago summer. The singer recounts all the wonderful things he loves about the city – from its beaches to its pizza and hotdogs.

He describes his time in Chicago as “like a dream” and celebrates the city for being simply “The El”. A perfect tune for an evening drive along Lake Michigan or a summer party in the park.

The Night Chicago Died By Paper Lace.

The Night Chicago Died is an upbeat rock song by the British band Paper Lace. The lyrics describe the fictional story of a police officer whose family is killed in the riots that occurred on July 24, 1919 in Chicago.

The song paints a vivid picture of the chaos and destruction caused by the riots and serves as a cautionary tale about its destructive power.

Think by Aretha Franklin.

Aretha Franklin’s song “Think” stands out as a tribute to the city of Chicago. The soulful track, written and produced by Aretha herself is an ode to the Windy City and its inhabitants.

With lyrics like “No one can love you better than Chicago can / No matter how much you try they’ll understand”, it’s clear that Aretha wanted to honor the city with her music.

The song features heavy brass instruments and a funky bassline, giving it an upbeat feeling that captures the energy of Chicago’s culture.

It also has a strong message of unity and resilience, reminding listeners of the power of people when working together for common goals. In this way, “Think” celebrates the city of Chicago and all who live there.

This City by Patrick Stump and Lupe Fiasco.

This song is about Chicago and the struggles it deals with as a city. The lyrics talk about poverty, crime, and racism that are still prevalent in the city.

Lupe Fiasco raps about how he grew up in the South Side of Chicago and was surrounded by violence, drugs, and poverty. Patrick Stump sings about how there is hope in the city despite all of the struggles, and how everyone is working together to make it a better place for future generations.

The song is a powerful reminder that Chicago has overcome difficult times before and can continue to do so in the future. It also reminds us of the importance of standing together as a community and fighting for what’s right.

Tonight, Tonight By Smashing Pumpkins.

Released on the 1996 album Mellon Collie and the Infinite Sadness, “Tonight, Tonight” is one of the most popular songs by Smashing Pumpkins. The alternative rock band’s frontman Billy Corgan wrote the song about two lovers who run away to Chicago in search of a better life.

With its anthemic chorus, ‘Tonight, tonight, the world is wide and tomorrow / We can all run free; tonight, tonight; the fires of forever shine’, this song captures the romanticized view of Chicago as a city of hope.

The lyrics also explore themes such as freedom, escape from reality, and a new beginning. In addition to its positive message about Chicago, “Tonight, Tonight” is also praised for its unique arrangement and instrumentation.

A combination of guitar-driven riffs, strings, and percussion gives the song a driving rock sound that makes it one of Smashing Pumpkin’s most beloved songs. This timeless track continues to be a favorite among fans of all ages.

Via Chicago by Wilco.

This track is part of the alt-country band Wilco’s third album, Summerteeth. It’s a song about frontman Jeff Tweedy’s experience in Chicago and his reflections on the city and its people. The lyrics are eclectic and spare; reflecting on more abstract themes such as “the worm of doubt” that makes it hard to feel at home.

The song has a quiet and sparse arrangement, recalling the folk-rock style of Bob Dylan’s Blood on the Tracks album. It captures the melancholy mood of living in an urban environment while simultaneously expressing love for its vibrant culture.

Via Chicago serves as a testament to Wilco’s incredible knack for storytelling, with its emotionally raw and honest lyrics. The song is a great representation of the band’s unique style, and its melancholic atmosphere will leave you feeling both inspired and reflective.

Windy City By Phish.

This rock song by the American rock band Phish pays homage to Chicago, celebrating its unique and captivating spirit. The chorus is a direct nod to the Windy City with lines like “Oh, windy city keep my feet on the ground” and “The windy city soon will be mine.”

The guitar riffs and driving drums of the song offer an energetic and upbeat ode to this great city.


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