27 Best Chicago Rappers Of All Time

Rappers from Chicago are part of a long tradition of great music. Rap, in particular, is a significant part of Chicago’s musical contribution to the world. If you’re a fan of finding new rap artists to follow, it’s best to watch out for this city. They always have someone new and exciting to listen to.

We have put together a list of the 27 best Chicago rappers. You’ll find established stars on this list, but there may also be some new names you’ll want to add to your playlist.

Before you start shaking your fists, understand that these artists aren’t necessarily in order of greatness, they are simply some of our favorites from Chicago.

1. Common

Common - Come Close (Official Music Video) ft. Mary J. Blige

Common is one of the most versatile rap artists in the industry. He has won a Golden Globe and an Academy Award for Best Original Song for his work on Glory. He and John Legend wrote that one together. His debut album, Can I Borrow a Dollar? came out in 1992 to great success. He’s followed that up time and time again with seemingly endless creative inspiration. Common is a fountain of talent, and we’re glad it never runs out.

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2. Queen Key

Queen Key - This The way (Official Video)

Queen Key could also be called the Queen of Girl Power and Hip Hop Humor. She takes her music seriously, but she also brings a sense of fun to everything she does. Fans love her irreverent but poetic style and hilarious perspective on the world. When you listen to Queen Key, you should be ready to be shocked until you laugh. That’s why fans have found that listening to her tracks is always a pleasure.

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3. femdot.

femdot. - "Senegalese" (Official Music Video)

Femdot. is known for lyrics that express personal experiences and raw emotions. He’s also open about wanting his work to touch his audience. “Wrote this cause it helped me,” he once said. “But maybe it can help you too,” he added rather than focus on telling his story for himself alone, Femdot. has gained a following by being an empathetic rapper who understands his fans sometimes need music as much as he does. 

4. Taylor Bennett

Taylor Bennett - Grown Up Fairy Tales (feat. Chance the Rapper & Jeremih)

Chance the Rapper’s brother Taylor Bennett came out as bisexual, establishing him as a queer icon for modern rap. However, his artistry is much more than his sexual identity or his relationship to Chance the Rapper. Taylor Bennett is a talented performer in his own right. His work is heavily influenced by other artists, and he is known for including an eclectic mix of styles in his music.

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5. G Herbo

G Herbo - Sessions (Official Video)

G Herbo, also known as Lil Herb, has been featured on Billboard 200 and is known both for his excellent music and his charitable contributions to kids in the community where he grew up. Because of this, his talent and his efforts to give back to kids have made him a fan favorite among rap audiences, especially those in Chicago, where it’s easiest to see his impact. 

6. Lil Durk

Lil Durk - Risky (Official Video)

Lil Durk rose to fame with his mixtape series, Signed to the Streets, in 2013. From then, he signed with Def Jam Recordings until he moved on in 2018. He’s been nominated for an (NAACP) Image Award for his music, and it’s only a matter of time before he takes home a win. 

7. Calboy

Calboy - Envy Me (Official Video)

Also known as 147Calboy, this artist features music that is influenced by a wide variety of performers, including Chance the Rapper, Michael Jackson, and The All American Rejects. The result is a unique sound that is all his own. Fans who are new to him often wonder how they’re supposed to pronounce his name. When you realize that it’s a play on words to combine his name (Calvin) with “cowboy,” it should be clearer.

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8. Joseph Chilliams

Joseph Chilliams - Azula ft. FIG (Lyric Video)

Joseph Chilliams has a special ability to make people laugh and smile. He uses this power for good in his work, from his dancing to his rapping, building a name for himself as one of the best comedy rappers out there. This is a man who puts his heart and soul into his music, and he always aims to put a smile on the audience’s faces. So far, he’s been a roaring success. 

9. Earl Sweatshirt

Earl Sweatshirt - 2010 (Official Video)

Earl Sweatshirt isn’t your average rapper. He’s been noted for his experimental hip hop styles and has been called a Hip Hop Prodigy. Perhaps this isn’t so surprising, considering his mother is an academic, and his father was a poet and political activist. He’s been nominated for a Grammy Award and won an MTVU Breaking Woodie Award

10. Open Mike Eagle

Open Mike Eagle - I'll Fight You produced by Diamond D (official video)

Open Mike Eagle is another in the growing genre of hip hop humor or comedian rap. He’s an established and talented performer who knows how to entertain and get a laugh when he needs it. This genre of funny rap is flourishing with amazing tracks like the ones Open Mike Eagle puts out. Fans have made it clear they need more of this off-beat subgenre. 

11. Fredo Santana

Fredo Santana - Pass Me My Double Cup (Official Video) Shot By @AZaeProduction

Fredo Santana, cousin of rapper Chief Keef, tragically died of a seizure in 2018, cutting short a promising life and career in music. During his active years, he released several amazing songs and is fondly remembered by fans. His songs remain popular today. 

12. Noname

Noname is an important voice in the rap industry today. Poet, performer, and producer, she also runs a book club for radical texts by authors of color. Noname’s efforts to elevate music and poetry to marginalized spaces and broader artistic endeavors have been championed by many of her peers. 

13. Chance the Rapper

Chance the Rapper - Same Drugs (Official Video)

Chance the Rapper has already been mentioned several times on this list. He’s related to important names in the industry, and he has collaborated with many others. Since his start in 2011, Chance the Rapper has gained mainstream success and appeal for his great sound.

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14. Lupe Fiasco

Lupe Fiasco - The Show Goes On

Lupe Fiasco is another performer who has achieved mainstream success. In 2006, GQ Magazine named him one of their Men of the Year. Two years later, he won a Grammy Award. Because he is a genre-crossing super talent, he is also the frontman for the rock band Japanese Cartoon. 

15. Vic Mensa

Vic Mensa - U Mad (Official Music Video) ft. Kanye West

Vic Mensa has been nominated for a Grammy Award and famously speaks out – sometimes in controversial situations – against what he sees as a trend in hip-hop of “championing” men who abuse women. His music is influential in the genre. 

16. Chief Keef

Chief Keef - I Don't Like ft. Lil Reese

Chief Keef has become known as a leader in the drill subgenre of hip hop. This is a trap-influenced interpretation of gangster rap that is a fascinating evolution of the genre. His interest in experimenting with music has led to many fans who can’t get enough of his work.

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17. Psalm One

Psalm One - Need Love Too

Also known as Hologram Kizzie, Psalm One has been prolific in her career. Releasing several albums, mixtapes, singles, and collaborations, she has emerged as a strong voice in the hip hop genre. She’s been a member of several groups, including Nacrobats, Rapperchicks, and Big Silky. 

18. Twista

Also known as Tung Twista, this artist is aptly named for his ability to rap quickly. So quickly, in fact, that he made the Guinness Book of World Records in 1992 for pronouncing 598 syllables in under a minute. He’s used that talent to wow audiences with chopper-style rapping.   

19. Add-2

Add-2 - Stop Play Rewind ft. Rapsody

Add-2 gained popularity with the release of his mixtape A Tale of Two’s City: Volume 2 in 2007. He’s gone on to be featured on MTV and to work with musical giants Kendrick Lamar and The Roots. Now, with several mixtapes, albums, and collaborations to his name, he continues to be a rising star in rap.

20. Qwazaar

Qwazaar & Batsauce - Reach

Known as an underground hip hop artist, Qwazaar co-founded the rap group Typical Cats and is a member of Outerlimitz. Frequently collaborating with others is the name of the game for Qwazaar, and this choice has led to him increasing his visibility as a major player in the rap game.   

21. Joey Purp

Joey Purp - Elastic

Joey Purp is a member of the Leather Corduroys, which is part of his hip hop collective, SAVEMONEY. He’s been influenced by an eclectic range of musical artists, including the Wu-Tang Clan, Sex Pistols, and The Velvet Underground. The result has been a unique sound that has brought something special to his mixtapes and his debut album, Quarterthing.

22. Famous Dex

Famous Dex - Japan (Prod. JGramm) [Official Lyric Video]

Famous Dex released his debut album in 2018. It was called Dex Meets Dexter, and it went to the twelfth position on the Billboard 200 chart, an amazing feat for a new artist. Because of substance abuse issues, he’s had some struggles with legal situations and other controversial topics. However, he has made some steps to get help so that he can continue to thrill audiences with his promising talent.

23. Da Brat

Da Brat - That's What I'm Looking For

Da Brat is another queer icon in the rap industry, which is important to fans because there isn’t significant representation for LGBTQ+ fans. Though she dated Allen Iverson for a while, she eventually came out as a lesbian and talked about why it took her a long time to be honest with herself and her fans. Now, she’s still a relevant player in the rap industry, collaborating with some of the top names and releasing hit tracks. In 1994, her debut album, Funkdafied, became the first female solo rap album to be certified Platinum.

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24. Polo G

Polo G - RAPSTAR (Official Video)

Polo G’s first album, Die a Legend, went Platinum after jumping to number six on the Billboard 200 chart. His second album, The Goat, reached number two on the Billboard 200 chart. At that point, he was officially a repeat mainstream success. Since then, he’s been nominated for two MTV Video Music Awards and a Brit Award for International Song of the Year. This is a rap artist who knows his craft and knows how to get his music out in ways that have strong emotional impacts on his audience. 

25. Supa Bwe

When Supa Bwe was a kid, he preferred bands like Rage Against the Machine and Korn. In other words, his early influences were not rap or hip hop at all. It was his father who introduced him to some of the greatest names in rap history and rounded out his musical education. Now, Supa Bwe makes music that stands out because it is born of punk, rock, and hip hop influences, creating a sound that is genuinely his own. 

26. Chuck Inglish

Chuck Inglish - "DAMAGE" (Official Music Video)

Chuck Inglish is mostly known for his work in The Cool Kids, but he also released an album, Convertibles, that was well received by fans. He has collaborated with some of the top names in the business. Though he takes his time on releases, fans know they can trust Chuck Inglish to truly deliver when it’s time for some great music.

27. Kanye West

Kanye West - Stronger

We can’t do a list of Chicago rappers without including Kanye. Though he has often found himself the source of intense controversy, there is little debate about his musical talent. Kanye West’s tracks are among the greatest hits of our time, not only in his genre, but in music in general. He has collaborated with top talent from around the world, often blurring genre lines and putting on amazing live performances as large-scale visual events. He may have a troubled history in many ways, but he is also possibly a musical genius.

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