The Best Chicago Rappers – Our Top 8 Picks!

The essence of Chicago lies in its rich music history. Furthermore, the city is quite famous for its well-known singers, rappers, bands, and musicians. It is impossible to ignore the contribution of best Chicago rappers to the rap music industry. Well, just like other groups of musicians, you will find different styles of rappers from different cultures in the neighborhoods of Chicago. The best rappers in Chicago have pioneered a unique and new sound that never fails to inspire people across the World. Here is a list of some of the most popular rappers in Chicago.

Best Chicago Rappers

Here’s a list of some of the most amazing rappers from Chicago who made a mark in the world.


Kanye West

Kanye West

Kanye West, also popularly known as Ye, was born in 1977. He is a well-known American fashion designer, record producer, and rapper and the owner and founder of GOOD Music. He has produced hundreds of singles for well-known music artists. In the mid-1990s, he began his career and then created a hip-hop group called Go-Getters by partnering with one of the best Chicago rappers Timm G and GLC. In 2002, he released his first solo album, The College Dropout. If you listen to the raps, you can feel that he is greatly influenced by the Chicago drip rap style.


Polo G

Polo G best chicago rappers

When talking about Chicago’s best rappers, it is impossible to forget Polo G.  Born in the year 1992, Polo G is a famous American rapper. He became popular with his all-time hits Pop Out and Finer Things. Besides, in 2019, he released Die a Legend, his debut album and that album was certified Platinum by the RIAA, and on the US Billboard 200, it ranked in the 6th position. Furthermore, the second album by Polo, The Goat, released in May 2020, ranked 2 on the Billboard list. His song, GNF, released on February 20, set the stage for the release of his third album.

Interesting Read: Do you why is Chicago called Windy City?


Chance The Rapper

Chance The Rapper

Hailing from the South side of Chicago, Chance is well-known for his rapping style. He raps quite well in different styles and has a distinct voice and flow that impresses all. Even though he is new in this industry, this young rapper has managed to corner a huge popularity and is already selling out venues.

What’s more? He is among the best Chicago rappers with a vibrant singing style and intricate wordplay have drawn comparisons to The Pharcyde and Eminem. He came to the limelight in the year 2013 when his two mixtapes were made public including 10 Day. Additionally, he also released Coloring Book, his 3rd mixtape, in the year 2016, and it witnessed instant success. Due to this, out of 7 Grammy nominations, he won Bennett three Grammys.


Lil Durk – Out of the Best Chicago Rappers

Lil Durk best chicago rappers

Born in 1992, Durk Derrick Banks is famous as Lil Durk in the rap music industry. He is a famous American singer as well as one of Chicago’s best rapper. From a young age, he developed an interest in music, and he released some popular mix tapes through his OTF-Only the Family label. After achieving huge success, he selected music as his full-time career. Later, he signed a contract with Def Jam Recording and is now rated as the best rapper to be connected with this recording label. 

After the success of these initial 2 singles, he released another mix tape, Life Ain’t No Joke, and it witnessed more than 210,000 downloads. In 2012, he released L’s Anthem featuring French Montana, which brought more popularity. Speaking about his achievement and awards, in 2016, the Underground Interviews, a famous music blog, named Lil Durk as the Rapper of the year.


Chief Keef

Chief Keef

Chief Keef, or Keith Kozart, is one of the best rappers in Chicago, and he is also a well-known mixtape artist and record producer. Born in 1995, Chief Keef gained notoriety with the help of his fellow rappers like Fredo Santana, Lil Reese, and Lil Durk. Finally, Rich, his debut album, which was released in 2012, ranked 5 on the Billboard 200 album chart. Besides, his album, I Don’t Like, was certified Platinum by the Recording Industry Association of America. After the huge success of I Don’t Like, he created his own remix version of the album by partnering with famed rappers like Pusha T and Big Sean. By 2012, Chief Keef became the most popular rapper among record labels.


G Herbo – Among Best Chicago Rappers

G Herbo best chicago rappers

Born in 1995, G Herbo is an American songwriter as well as a rapper who became famous for his mixtape Welcome to Fazoland. Besides, this rapper from Chicago has other mixtapes such as Strictly 4 My Fans, Pistol P Project, Ballin Like I’m Kobe, and many more. Moreover, he is also well-known for his two highly acclaimed EPs, i.e., Strictly 4 My Fans 2- Road to Humble Beast and Welcome to Fazoland 1.5. He works with Machined Entertainment Group.


King Louie

King Louie

With a rapping style best defined as a pot of gumbo, King Louie hails from the Dro City neighborhood. With his unique dialect and arrogant attitude, this Chicago’s best rapper has become quite popular among people in Chicago. His album Too Coo witnessed huge success. In 2012, he partnered with a local pizza store for its limited-edition pizza and created a short video with his unique moves, The Val Venis, which remained as a trending post on Twitter for months, and that made the real pro wrestler Val Venis to call the rapper.



Calboy best chicago rappers

Calboy or Calvi Lashon Woods is a songwriter, singer, and rapper. He is among the best Chicago rappers and has signed a contract with Paper Gang Inc. and also has a partnership with RCA Records and Polo Grounds. He became popular with his albums Calboy the Wild Boy and ANXIETY. His song Envy Me also witnessed huge success in the rap industry.


It can be said that Chicago has paved the way for some well-known rappers. One of the best Chicago rappers, Kanye West, who has won a Grammy award, will remain a legend in the rap industry. But young rappers are also gaining momentum with time. For example, Chief Keef, King Louie, and more. The list of the best rappers in Chicago will go on. If you are a fan of rap music, then don’t forget to listen to the mix tapes or albums of these rappers. 

Want to be a rapper? Check out these Karaoke bars in Chicago.

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