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The 20 Best Rappers From Chicago

Photograph of the blog post author, Sebastian Wolf

Sebastian Wolf


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Best rappers from Chicago

Chicago has a rich history in hip-hop, with some of the genre’s most influential and talented artists hailing from the Windy City. From the early days of Common and Kanye West to the modern sounds of Chance the Rapper and Noname, Chicago has produced a diverse range of rappers who have left their mark on the industry. In this article, we’ll be taking a look at the 20 best rappers from Chicago, exploring their unique styles, lyrical prowess, and impact on the city’s music scene. From drill music to conscious rap, Chicago has it all, and we’ll be delving into the careers of artists who have become household names, as well as those who are still making their mark on the industry. 

Whether you’re a die-hard hip-hop fan or simply curious about the Chicago rap scene, this article will provide an in-depth look at the city’s most talented and influential rappers. So, without further ado, let’s dive into the world of Chicago hip-hop and explore the 20 best rappers the city has to offer.

The Chicago Rap Scene

Chicago rap scene

Emerging in the late 1980s and early 1990s, Chicago rap was heavily influenced by the city’s rich history of blues and jazz music. The early pioneers of the genre, such as Twista and Do or Die, helped establish Chicago as a major player in the rap world. However, it wasn’t until the mid-2000s that the scene really began to take off, with the emergence of artists such as Kanye West, Lupe Fiasco, and Common. These artists brought a new level of creativity and innovation to the genre, blending elements of soul, funk, and electronic music with traditional hip-hop beats and rhymes.

The impact of the Chicago rap scene can be seen in the way it has influenced other artists and genres. Many of today’s most popular rappers, such as Chance the Rapper and Vic Mensa, hail from Chicago and have been heavily influenced by the city’s rich musical history. Additionally, the Chicago scene has helped pave the way for other regional rap scenes, such as those in Atlanta and Houston, by demonstrating the power of local talent and the importance of community support. Overall, the impact of the Chicago rap scene on hip-hop music and culture cannot be overstated, and its legacy will continue to be felt for years to come.

The 20 Best Rappers From Chicago

From international megastars to underground heroes, the Windy City has it all. Here’s our list of the 20 best rappers from Chicago:

World Famous Rappers From Chicago: Kanye West

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Kanye West is an American rapper, producer, and fashion designer known for his innovative and controversial approach to music and art. He first gained recognition in the early 2000s for producing hit songs for artists such as Jay-Z and Alicia Keys before launching his own successful solo career. West’s music often features themes of personal struggle, faith, and social commentary, and he has been praised for his ability to blend genres and push the boundaries of traditional hip-hop. However, his outspoken and sometimes erratic behaviour has also garnered criticism and controversy throughout his career, including his public support of controversial political figures, allegations of anti-semitism, and his public feuds with other artists and media outlets.

Lupe Fiasco

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Lupe Fiasco is a rapper, producer, and entrepreneur from Chicago, Illinois. He first gained recognition for his mixtapes in the mid-2000s and signed with Atlantic Records in 2006. His debut album, “Lupe Fiasco’s Food & Liquor”, was critically acclaimed and earned him three Grammy nominations. He continued to release successful albums, including “The Cool” and “Lasers”, and collaborated with other artists such as Kanye West and Pharrell Williams.

Fiasco is known for his socially conscious lyrics and has been involved in various activism efforts, including supporting education and raising awareness about food insecurity. He has also pursued business ventures, including founding his own record label and a non-profit organisation.

Chief Keef

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Chief Keef rose to fame in 2012 with his debut single “I Don’t Like”, which was remixed by Kanye West and propelled Keef into the mainstream. Keef’s music features aggressive and often violent lyrics, which reflect his experiences growing up in Chicago’s South Side. He has been credited with popularising the drill subgenre of hip-hop, famous for its dark and menacing beats. Despite his success, Keef has had a turbulent personal life, including legal issues and conflicts with other rappers.

Chance the Rapper

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First gaining widespread recognition with his 2013 mixtape “Acid Rap” 2013. Chance the Rapper’s music is known for its positive and uplifting themes. He often addresses social issues such as gun violence and education reform with his lyrics. He has won several awards, including three Grammy Awards, and has collaborated with artists such as Kanye West, Justin Bieber, and Childish Gambino. 

Chance is also known for his philanthropic efforts, particularly in his hometown of Chicago, where he has donated millions of dollars to public schools and other charitable causes.

Emo Rappers From Chicago: Juice WRLD

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Juice WRLD was an American rapper, singer, and songwriter. He gained popularity with his emo-rap style and introspective lyrics, often touching on themes of heartbreak, mental health, and drug use. Born Jarad Anthony Higgins, he was famous for his freestyle flows and ability to incorporate a wide range of musical influences in his music. He released his debut studio album, “Goodbye & Good Riddance”, in 2018, along with the hit single “Lucid Dreams”.

Tragically, Juice WRLD passed away in December 2019 at the age of 21 due to a drug overdose. Despite his short career, he left a lasting impact on the music industry and his fans.

King Louie

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King Louie is a Chicago-based rapper known for his unique style and sound. He first gained recognition in the early 2010s with his mixtapes and collaborations with fellow Chicago artists, such as Chief Keef and Lil Durk. King Louie’s music often features heavy bass and trap beats. His lyrics touch on topics such as street life, drugs, and violence. 

He has faced his own share of struggles, including being shot multiple times in 2015. Despite these challenges, King Louie has continued to release music and maintain a loyal fanbase. He remains a prominent figure in the Chicago rap scene.

Lil Durk

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Lil Durk began his career with a series of mixtapes, including the “I’m a Hitta” series and “Life Ain’t No Joke”. He signed with Def Jam Recordings in 2018 and has since released several successful albums, including “Signed to the Streets 3” and “Just Cause Y’all Waited 2”. Lil Durk is known for his emotional and introspective lyrics, often detailing his experiences with poverty, violence, and loss. 

He has collaborated with many notable artists, including Drake, Polo G, and Lil Baby, and has become a prominent figure in the current wave of melodic rap.

Da Brat

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Da Brat, born Shawntae Harris, is an American rapper and actress from Joliet, Illinois. She first gained attention in the early 1990s with her debut album “Funkdafied”, which went platinum and earned her a Grammy nomination. Da Brat’s unique flow and confident delivery made her stand out in a male-dominated industry. She continued to release successful albums throughout the 90s and early 2000s, collaborating with artists such as Mariah Carey and Missy Elliott. 

In addition to her music career, Da Brat has also made appearances in several films and television shows, including “Empire” and “Growing Up Hip Hop: Atlanta”. She remains a respected figure in hip-hop and a trailblazer for female rappers.


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Twista, born Carl Terrell Mitchell, gained recognition in the 1990s with his rapid-fire flow and intricate rhyme schemes. Known for his unique style and ability to deliver complex lyrics at lightning-fast speeds, he earned the title of “fastest rapper in the world” by the Guinness World Records in 1992. Twista released his debut album, “Runnin’ Off at da Mouth”, in 1991. However, it was his third album, “Adrenaline Rush”, that brought him mainstream success in 1997. 

He has since released several successful albums, collaborating with notable artists such as Kanye West, Ludacris, and Jamie Foxx.

Soulja Boy

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Soulja Boy, also known as DeAndre Cortez Way, is an American rapper, record producer, and entrepreneur. He rose to fame in 2007 with his hit single “Crank That (Soulja Boy)”. The track topped the US Billboard Hot 100 chart and became a viral dance craze. Soulja Boy has released several successful albums and mixtapes throughout his career, including “iSouljaBoyTellem” and “Young Drako”. 

In addition to his music career, Soulja Boy has also ventured into other industries, such as fashion and gaming. He has been praised for his entrepreneurial spirit and ability to adapt to changing trends in the entertainment industry.


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Dreezy is an American rapper, singer, and songwriter from Chicago, Illinois. She gained popularity with her debut mixtape “Schizo” in 2014, featuring collaborations with fellow Chicago artists such as Common and Jeremih. Dreezy’s music often explores themes of empowerment, relationships, and social issues. She has since released two studio albums, “No Hard Feelings” in 2016 and “Big Dreez” in 2019, both of which received critical acclaim. 

Dreezy has also collaborated with a variety of other artists, including Gucci Mane, 6LACK, and Kash Doll. She is famous for her versatile flow and ability to seamlessly switch between rapping and singing.

Underground Rappers From Chicago: Psalm One

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Psalm One, also known as Hologram Kizzie, is a rapper and record label owner. She has been active in the underground hip-hop scene since the early 2000s and has released several critically acclaimed albums, including “The Death of Frequent Flyer” and “Flight of the Wig”. Psalm One is known for her clever wordplay, introspective lyrics, and unique flow. She has collaborated with a variety of artists, including Open Mike Eagle, MF DOOM, and Atmosphere. 

Further to her music career, Psalm One is also a teacher and mentor, helping young people in Chicago to develop artistic skills.

Earl Sweatshirt

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Earl Sweatshirt is an American rapper, songwriter, and record producer. He gained popularity as a member of the hip-hop collective Odd Future and later as a solo artist. Earl’s music is known for its introspective and often dark themes, as well as its intricate lyricism and unconventional production. He has released several critically acclaimed albums, including “Doris” and “Some Rap Songs”. 

Earl is also known for his reclusive nature and reluctance to engage with the media or public events. Nevertheless, he has a loyal fanbase and is widely respected in the community for his unique style and artistic vision.

Influential Rappers From Chicago: Common

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Common, born Lonnie Rashid Lynn Jr., is an American rapper, actor, and writer. He first gained recognition in the early 1990s as part of the underground hip-hop scene in Chicago and later achieved mainstream success with his album “Like Water for Chocolate” in 2000. Common is known for his socially conscious lyrics, receiving praised for his ability to address issues such as race, poverty, and injustice in his music. 

He has won multiple Grammy Awards and has also acted in films such as “Selma” and “John Wick: Chapter 2”. In addition to his music and acting career, Common is also an author and activist, working to promote education and social justice.

Open Mike Eagle

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Open Mike Eagle is a rapper, comedian, and podcast host. He’s famous for his unique style of socially conscious and introspective hip-hop, often exploring themes of race, identity, and personal struggles. Eagle has released several critically acclaimed albums, including “Dark Comedy” and “Brick Body Kids Still Daydream”. Furthermore, he’s collaborated with a wide range of artists, from indie rockers to fellow rappers. 

In addition to his music career, Eagle has made a name for himself as a comedian. He has appeared on shows like “The Eric Andre Show” and hosts his own podcast, “What Had Happened Was”.


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Noname is a rapper, poet, and activist from Chicago, Illinois. She gained recognition for her features on Chance the Rapper’s early mixtapes, releasing her own debut mixtape, “Telefone”, in 2016. Noname’s music is known for its introspective and socially conscious lyrics, as well as its jazzy and soulful production. Her style blends elements of spoken word poetry, neo-soul, and hip-hop, creating a unique sound that has earned her critical acclaim. Noname has also been vocal about her political beliefs and activism. She uses her platform to advocate for issues such as police brutality and racial justice.

Polo G

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Polo G, born Taurus Bartlett in Chicago in 1999, is an American rapper and songwriter. He first gained attention with his debut single “Finer Things”, in 2018, which quickly went viral on social media. His debut album, “Die a Legend”, was released in 2019, peaking at number six on the US Billboard 200 chart. 

Polo G is famous for his introspective lyrics and his ability to tell stories about life in the inner city. He has collaborated with several artists, including Lil Tjay, Juice WRLD, and The Kid Laroi. In 2021, he released his Billboard 200 chart-topping third studio album, “Hall of Fame”.


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Calboy, whose real name is Calvin Woods, is a rising rapper from Chicago. He came to attention with his 2018 viral hit “Envy Me”, peaking at number 31 on the Billboard Hot 100. Calboy’s music is characterized by his emotive and melodic flow, often touching on themes of pain, struggle, and perseverance. He has collaborated with several notable artists, including Polo G, Lil Tjay, and Meek Mill. Calboy’s debut studio album, “Wildboy”, was released in 2019 and received positive reviews from critics. He continues to gain popularity and is considered one of the most promising young artists in the rap scene.

Up-and-Coming Rappers From Chicago: Queen Key

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Queen Key is a rising female rapper who has been making waves in the hip-hop scene. Known for her bold and unapologetic lyrics, she has gained a loyal following with her unique style and confident delivery. Queen Key’s music often touches on themes of empowerment, sexuality, and street life. Her lyrics frequently reflect her own experiences growing up on the South Side of Chicago. She released her breakout mixtape in 2017, showcasing her raw talent and potential as an artist. Since then, she has continued to release music and collaborate with other artists, solidifying her place as a force to be reckoned with in the rap game.

Montana of 300

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Montana of 300, born Walter Anthony Bradford, is an American rapper, songwriter, and record producer from Chicago, Illinois. He gained fame for his unique style of rap, which features fast-paced and complex rhymes over trap beats. Montana of 300 first gained attention with his viral “Chiraq” remix, helping him to gain a significant following.

He has since released multiple mixtapes and albums, including “Fire in the Church” and “A Gun in the Teacher’s Desk”. Montana of 300’s music often touches on themes of struggle, perseverance, and success. Additionally, he is famous for his high-energy live performances.

Impact of the Best Rappers From Chicago

Impact of the best rappers from Chicago

Chicago has consistently produced some of the most influential and innovative voices in hip-hop, and their impact is undeniable. These artists have not only put their city on the map but also brought attention to the issues facing their communities, from gun violence to poverty. They have used their platforms to advocate for change, inspiring a new generation of artists to follow in their footsteps. 

Furthermore, the impact of Chicago’s rap scene extends beyond just music. It has influenced fashion, art, and culture at large. The city’s unique blend of sounds and styles has helped to shape the genre as a whole. In doing so, Chicago has proven that hip-hop is about more than just East Coast vs West Coast. As it continues to produce talented and socially conscious artists, it’s clear that the Chicago rap scene will further grow and shape the future of hip-hop itself.


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