Chicago, also known as the Windy City or Chi-town , is home to some of the most influential artists in the American rap scene. These hip-hop artists have adopted both the East Coast's lyricism and the West Coast's swagger. Some of the top Chicago rappers who have influenced the global drill scene include Kanye West , Polo G , and Common .

Key takeaways

Who are the top Chicago rappers?

Compiling the list of the top Chicago rappers who changed the game and influenced the global Hip-hop scene is subjective and not exhaustive. It includes both late and living artists and is based on a combination of factors such as chart performance, critical acclaim, and societal influence. Below is an unordered list of Chi-Town legends who forever changed the landscape of rap for their hometown.

1. Polo G

Polo G is a prominent American rapper born and raised in Chicago, Illinois. He rose to fame with his hit singles Finer Things and Pop Out . Polo G released his debut album Die a Legend in 2019 and has since released three subsequent albums.

2. Chance the Rapper

Chance the Rapper is a rapper, singer, songwriter, and record producer from the United States. He gained widespread recognition as one of the underground Chicago rappers through his two mixtapes, Acid Rap and Coloring Book . His Coloring Book mixtape was the first streaming-only album to win a Grammy Award for Best Rap Album.

3. Lupe Fiasco

Lupe Fiasco is a respected and intellectual American rapper from Chicago. He is best known for his complex lyrics and thought-provoking music , which uses intricate wordplay and metaphors.

Lupe Fiasco was a guest star on Kanye West's single Touch the Sky in 2006. He released his debut album Lupe Fiasco's Food & Liquor in 2006, receiving widespread critical acclaim.

4. Twista

Twista is a well-known rapper from Chicago, Illinois. He is widely recognized for his incredibly fast rapping, known as the "chopper" style of rapping. Twista held the 1992 Guinness World Record holder for the fastest English-speaking rapper.

Twista debuted his career in 1992 when he released his first album Runnin' Off at da Mouth under the moniker Tung Twist. The rapper's 2004 album Kamikaze hit number one on the Billboard 200 chart thanks to the single Slow Jamz featuring Jamie Foxx and Kanye West.

5. Common

Common, formerly known as Common Sense is one of the most respected figures in American hip-hop. He is widely known for his thoughtful lyrics, versatile artistic expression, and smooth delivery.

Common has earned accolades, including Grammy Awards, an Academy Award, and an Emmy Award, both in music and film. Some of his albums include Can I Borrow a Dollar? , Finding Forever , Black America Again , and A Beautiful Revolution .

6. Famous Dex

Famous Dex is an American rapper best known for his energetic style and presence in the rap scene. He gained widespread recognition with his mixtape Dexter's Laboratory .

The rapper is also known for hit singles like Pick It Up and Japan , which charted on the Billboard Hot 100. He has collaborated with notable rappers like A$AP Rocky, Lil Yachty, and Rich The Kid.

7. Tink

Tink is a versatile artist known for her ability to blend rap and R&B vocals. She has risen to become one of the top female Chicago rappers.

The singer-songwriter is known for her numerous mixtapes and albums, including Winter's Diary , Dex Meets Dexter , Pillow Talk , and Think Tink . Tink has collaborated with notable artists including 2 Chainz, Muni Long, Fabolous, Russ and G Herbo.

8. CupcakKe

CupcakKe is a female Chicago rapper known for her unique style and explicit lyrics. She gained widespread attention for her unapologetically humorous lyrics challenging social norms, and pushing boundaries. The rapper has released numerous albums including Audacious , Ephorize , and Dauntless Manifesto .

9. Lil Eazzyy

Lil Eazzyy is a Chicago-based rapper and businessman. He gained traction with his single Onna Come Up , which was very successful.

Eazzyy's early success led him to sign a deal with Atlantic Records. He has released numerous mixtapes and albums, including Rookie Of The Year , Too Eazzyy , and Underrated . Besides music, Lil Eazzyy is the president of Rich & Ruthless Records.

10. Kanye West

Kanye West, also known as Ye, is perhaps the most famous rapper and producer from Chicago. He is a highly influential and controversial figure in the music and fashion scenes.

Ye rose to prominence as an artist and producer for Roc-A-Fella Records in the early 2000s. His works include Late Registration , Graduation , 808s and Heartbreak , and My Beautiful Dark Twisted Fantasy .

11. Saba

Saba is a renowned rapper and record producer from the United States. He grew up in the Austin West Side of Chicago rising to become one of the best Chicago rappers.

In 2013, he joined Chance the Rapper on his mixtape Acid Rap , performing the song Everybody's Something . Saba's albums include Bucket List Project , Care for Me , and Few Good Things .

12. Da Brat

Da Brat is one of the top 90s rappers who was born and raised in Chicago. She debuted her music career in 1992 after signing with Jermaine Dupri's So So Def Recordings in 1994. Da Brat released her debut album, Funkdafied the same year. The album made her the first female solo rap artist to have a platinum-selling debut album.

13. Chief Keef

Chief Keef is a highly influential and one of the new Chicago rappers. He is widely recognised for popularizing the drill music subgenre. Chief Keef gained much attention in the early 2010s with his mixtapes. He dropped his hit single I Don't Like in 2012 one of the songs in his debut album, Finally Rich.

14. Dreezy

Dreezy is one of the famous female Chicago rappers. She gained traction with her rapping and singing capabilities, combining with R&B hooks and pop-trap.

Dreezy got signed with Interscope Records in 2014, releasing her debut studio album No Hard Feelings in 2016. Three years later she dropped her second album Big Dreez in 2019 and a collaboration album Hitgirl in 2022 with Hit-Boy.

15. Vic Mensa

Vic Mensa is a rapper, actor, and activist. He began his career as one of the members of the group Kids These Days. Vic Mensa later went solo releasing his album The Autobiography in 2017 and later in 2023, he released Victor . The rapper has collaborated with other rappers like Kanye West and Jay-Z.

16. Rockie Fresh

Rockie Fresh is a rapper who has made a name for himself in the hip-hop scene. He began his music career in 2009 after releasing his first mixtape Rockie's Modern Life .

Andrew Schulz's net worth following Kendrick Lamar's beef: is he affected?

Rockie was signed early on by Rick Ross's Maybach Music Group (MMG). The rapper's only studio album Destination was released in 2019. He has multiple mixtapes including The Otherside , Driving 88 , and The Night I Went To .

17. Fredo Santana

Fredo Santana is an American rapper and older cousin of fellow rapper Chief Keef. He gained significant fame in early 2010 in the Chicago drill scene.

Fredo Santana released his first studio album, Trappin' Ain't Dead in 2013 and his second album, Fredo Krueger 2 in 2017. The rapper sadly passed away on 19 January 2018, after having a seizure.

18. Mick Jenkins

The Chicago-based rapper is recognised for his socially conscious, and intelligent lyrics which are a mix of jazz, soul, and hip-hop. He was signed to Cinematic Music Group and began his career in the mid-2010s.

Jenkins released his breakout mixtape, The Waters in 2014. The rapper followed the next year by releasing the Waves EP in 2015.

19. Joey Purp

Joseph Davis also known as Joey Purp, is a rapper from Chicago and one-half of Leather Corduroys. He gained much attention when he released iiiDrops mixtape in 2016 becoming one of the best rappers in the world. The rapper's latest release is the album Heavy Heart, Vol. 1 in 2023.

20. Rhymefest

Rhymefest is a rapper, songwriter, and activist from Chicago, Illinois. He is widely recognised for his writing work with fellow rapper Kanye West. Rhymefest wrote Kanye's hit songs Jesus Walks and New Slaves , with the former winning a Grammy Award.

The American songwriter also co-wrote Glory with Common and John Legend for the American film Selma , which won a Golden Globe Award and an Academy Award.

Is Kanye West a Chicago rapper?

Yes, Kanye West is a rapper from Chicago, Illinois. Although he was born in Atlanta, Georgia, he grew up in Chicago's South Shore neighbourhood.

Who is the most popular Chicago rapper?

Although choosing one rapper as the most popular is subjective, Kanye West is the most popular and influential rapper from Chicago. He is known for his innovative sound and influence in the rap industry.

What rappers are from O'Block?

Numerous rappers hail from O'Block which is an area in the South Side of Chicago, Illinois. They include Lil Durk, King Von, Chopsquad DJ, Tay Keith, and Hitmaka.

Chicago is home to some of the best rappers in the world. Chicago rappers like Polo G, Kanye West, Lupe Fiasco, and Common have been instrumental in putting the city on the global map.

Legit.ng published an article about the greatest Motown artists . Motown is an American record label that produced some of the greatest artists in the world. These artists' voices and sounds have been influential across generations.

Motown is a Detroit, Michigan record label founded by Berry Gordy Jr. in 1959. It was instrumental in the evolution of R&B, soul, and pop music in the 1960s and 1970s. Learn more about the greatest Motown artists.

Source: Legit.ng