Before the success of Chief Keef, Chicago hip hop as a whole was virtually non-existent and unknown to the outside world. But now Chicago has a massive pool of rappers who seem to bring different kinds of skills to the table.
Below is a complete list of the best Chicago rappers that didn’t limit their creativity in creating fine rap music that we all enjoy today.
Just scroll down and look who’s your favorite one!
1 Lil Durk
Hailing from Chicago, Lil Durk is a famous 28-year-old rapper. As a result of uploading his work on Myspace and YouTube, he rose to fame. Though he just made his breakthrough five years ago, the musician has been building his career since the 2010s.
2 Polo G
Polo G has become one of the most famous young rappers from Chicago after releasing hit singles Finer Things and Pop-Out. Furthermore, he also collaborated with many famous rappers to produce hit tracks for his fans. Polo G so far released three albums in June 2021.
3 Famous Dex
The legendary Dex loves to write his own songs. His first album ranked at number 12 on the Billboard 200 in the year 2018. His ten albums and EPs have made him one of the best rappers in Chicago.
4 Jhe Rooga
While growing his catalog, Jhe Rooga is still building a fan following. The rapper has produced numerous hit singles like Do Bout It, Scrappers, and For Duck. Currently signed to I Told You Records, he continues to dominate Chicago’s hip hop, RnB, and soul scenes.
5 G Herbo
Herbert Randall Wright III, also known as G Herbo (formerly Lil Herb), is a proud Chicago rapper born on October 8, 1995. The first studio album by this artist is Humble Beast which was released in 2017. His second studio album is Southside of 808 Mafia’s Swervo (2018), his third album, earned his first top-ten entry on the Billboard 200.
6 Chance The Rapper
Chancelor Johnathan Bennett, better known by the stage name Chance the Rapper, is another rapper and record producer from Chicago soil. He produced his first mixtape, 10 Day, in the year 2012.
However, his popularity grew after releasing his second mixtape, Acid Rap, in 2013. His third mixtape, Coloring Book, which he released in 2016, earned him the critical acclaim and attention he deserved. In addition to winning three Grammys, Coloring Book became the first streaming-only album to win a Grammy.
Born on April 3, 1999, Calvin Lashon Woods, better known by the stage name Calboy is a singer, rapper, and songwriter. His record label is Polo Grounds Music, and his record company is RCA Records. Calboy gained popularity after releasing the single “Envy Me” in 2018.
8 Lil Zay Osama
Isaiah Dukes, better known by Lil Zay Osama’s stage name, is a Chicago rapper who spent some time in jail. Lil Zay called his music “pain music” because his songs reflect a bad upbringing on the South Side of Chicago. He mostly talked about grief, trauma, and survival in his music. Osama started his rapping career at 8 and started recording at 10.
9 Mick Jenkins
Jayson Mick Jenkins, known professionally as Mick Jenkins, is a Chicago rapper currently signed to Cinematic Music Group. He released his first album, The Healing Component, in 2016 and his second album, Pieces of a Man, in 2018.
Born on May 30, 1996, Lucki Camel Jr. known professionally as Lucki (previously known as Lucki Eck$ and Luc) is a rapper and record producer based in Chicago, Illinois.
He came to the mainstream in 2013 after releasing his first project, Alternative Trap. Besides this, Lucki has collaborated with other prominent rappers like Chance the Rapper, FKA Twigs, Danny Brown, and Earl Sweatshirt. Currently, he signed to record label Empire.
Born on July 17, 1994, Tahj Malik Chandler, known professionally as Saba (stylized as SABA), is another rapper and record producer from Chicago.
Saba co-founded Pivot Gang with his brother Joseph Chilliams, their late cousin John Walt, and their high school friend MFn Mel. GETCOMFORTABLE and ComfortZone are two of Saba’s mixtapes that have gained him popularity.
12 Lil Bibby
Chicago rapper Brandon George Dickinson known professionally as Lil Bibby, started his career in 2011. Bibby released his first mixtape Free Crack in 2013. After signing the contract with Kemosabe Records, he released his second mixtape Free Crack 2, in 2014, and his third mixtape Free Crack 3, in 2015.
13 Juice Wrld
Jarad Anthony Higgins, better known by the stage name Juice Wrld (pronounced “juice world”; stylized as Juice WRLD) is another Chicago top rapper. Juice Wrld started his career in 2015 as an independent artist and signed a contract with Grade A Productions and Interscope Records in 2017.
However, he achieved glory after releasing his hit number “Lucid Dreams”, which ranked number two on the US Billboard Hot 100. Sadly, Juice Wrld left this world in 2019.
14 Lupe Fiasco
Born on February 16, 1982, Wasalu Muhammad Jaco known professionally as Lupe Fiasco, started his professional career at 18. However, he gained popularity in 2006 after his first album, Lupe Fiasco’s Food & Liquor.
His first album received three Grammy nominations. After the massive success of his first album, he released his second album in December 2007, titled Lupe Fiasco’s The Cool.
15 Da Brat
A significant part of the success of Chicago’s hip-hop scene was the involvement of its female rappers; one of them is Da Brat. Shawntae Harris, known as Da Brat, started her musical journey in 1992 when she signed with So So Def Records. Her first album Funkdafied sold one million copies, making her the first female solo to earn a platinum certification.
16 Bump J
Another famous rapper from Chicago is Terrance Michael Boykin, known professionally as Bump J. His rapping career is managed by SAL&CO. Bump J released his famous hit track “Move Around” in the year 2005.
This track earned her radio play and was included in the season Madden NFL 06. This song was also used in one of the McDonald’s commercials.
Another proud female rapper from Chicago is Elizabeth Eden Harris, better known as Cupcakke (often stylized as cupcakKe). She is famous for using hyper-sexualized, daring, and witty topics in her music.
Cupcakke started her musical journey by releasing singles in 2012. She achieved great recognition and popularity with her singles “Deepthroat” and “Vagina”.
18 King Louie
Louis King Johnson, Jr., aka King Louie (or King L), is a Chicago rapper who dominates the scene. Due to his hit singles, he was ranked one of the “hottest hip-hop” rappers of Chicago in 2012 by Spin Magazine.
19 King Von
Dayvon Daquan Bennett, known professionally as King Von, was another famous rapper from the land of Chicago, Illinois. He signed a contract with Lil Durk’s record label, Only the Family and Empire Distribution. Von released his first single, “Crazy Story,” after signing the contract, which became his breakout hit.
Rashawnna Guy, known professionally as Shawnna, is a female Chicago rapper who signed to Def Jam South through Ludacris’ Disturbing tha Peace Records. Shawnna’s songs and images are well known for their sexuality and rapid-fire delivery.
Her hit single “Stand Up” with Ludacris peaked at number one on the US Billboard Hot 100 in 2003, making her one of the rare female rappers to achieve this feat.
Fatimah Nyeema Warner, better known as Noname (pronounced “no-name”), is a Chicago-based rapper and record producer. She started her rapping career in 2010. Noname’s appearance in the hit single “Lost” from Chance the Rapper’s mixtape, Acid Rap earned him all the popularity and fame.
22 Fredo Santana
Known professionally as Fredo Santana, Derrick Coleman was the older cousin of Chicago rap king “Chief Keef.” On October 31, 2013, he released his first studio album, Trappin Ain’t Dead, via Savage Squad, which ranked at number 45 on the US Billboard 200. Unfortunately, Fredo left the world behind in 2018 at the age of 27.
Jeremy Phillip Felton better goes by the professional name Jeremih is a Chicago rapper, singer, and record producer. Def Jam Recordings signed him to a record deal in 2009. “Birthday Sex” was Jeremih’s debut single, ranking at number four on the US Billboard Hot 100 chart.
24 Kanye West
Known to the world as Kanye West, this gem of Chicago set his foot in the world of music as a producer for leading artists. However, He showed his skill to the world as a rapper by releasing his debut studio album, College Dropout, in 2004, which gained him all the fame and popularity he deserved for his incredible talent.
25 Chief Keef
Now we will talk about the king of Chicago rap Chief Keef, who is known to his neighborhood as Sosa, a name inspired by the kingpin Alejandro Sosa from Scarface’s movie.
Since he was a teenager, he has been involved in the rap scene and is often seen as representing Chicago’s gangsta rap culture. Besides being an artist, he’s also a producer with over 40 albums and mixtapes to his name.
Born on the 27th of November 1973, Carl Terrell Mitchell is around 48 years old. He rose to prominence with the release of his song, “Overnight Celebrity,” in the album “Kamikaze” in 2004.
So far, Twista has released eleven studio albums. “Runnin’ Off at da Mouth” was the first album, which came out in 1992.
27 Vic Mensa
This Chicago rapper was born on the 6th of June 1993 in Chicago, Illinois, USA. His complete name is Victor Kwesi Mensah. You can also call him “Vino.”
He is currently working with Roc Nation. Previously, he has also worked with Capitol Records, LLC, Def Jam Recordings, Closed Sessions, and Virgin EMI Records.
28 Open Mike Eagle
If Open is making things long, you can also call him “Mike Eagle.” He has been at it since 2004, and he has released five studio albums and several group albums as well.
He is 41 years old. By the way, his complete name is Michael W. Eagle II. He hails from Chicago, Illinois. His first album was “Unapologetic Art Rap.”
- Instagram account: @open_mike_eagle.
- YouTube account: Open Mike Eagle – Topic.
- Spotify account: Open Mike Eagle.
Who Is The Best Rapper From Chicago?
Every Chicago rapper has its importance in the industry, but Kanye West takes the crown as the best Chicago rapper right now.
Which Rappers Are From 63rd Street, Chicago?
Many rappers hail from 63rd Street, Chicago, or used slang in their rap songs, like “King Von,” Lil Durk,” and some others.
Who Is King Of Rap In Chicago?
You can disagree with this and have your own opinion, but “King Louie” is among those rappers who took the Chicago rapping industry to the top and can be considered the King of Rap in Chicago.