31 Best Chicago Rappers

Chicago has had a heavy influence on the rap scene over the years. As such, the Windy City is home to some of the best Illinois rappers.

While there are too many to list, this post contains the best Chicago rappers who need to be on your playlist.

Kanye West

Kanye Omari West was born in Atlanta, Georgia, in 1977 but grew up in Chicago after moving there with his mother when he was three.

West began his career in the mid-’90s, mainly making beats for other artists. After a serious car accident shattered West’s jaw, he released the song “Through the Wire,” a reference to his jaw being wired shut, in 2002, which would be his breakthrough hit.

Since then, West has released countless albums, mixtapes, and singles. He keeps close ties with his Chicago upbringing, even naming one of his children after the city.

Lil Durk

Durk Derrick Banks, or Lil Durk, was born in Chicago in 1992. His interest in rap led him to share his work on social media sites as a young teenager, which garnered some attention.

At 17, he became a father and decided to drop out of high school to join a street gang in Chicago called the Blood Gang. This decision marked the beginning of many run-ins with the law.

His rap career began in 2011 with his first two singles, “Sneak Dissin’”and “I’ma Hitta.” He has released seven solo albums since then, plus one album with the collective Only the Family, which he founded.

King Louie

King Louie, or King L, was born Lewis King Johnson, Jr. in 1987 in Chicago. Some have attributed King Louie to making Chicago the trendiest hip-hop spot in 2012.

King Louie released his first mixtape in 2007, entitled Boss Shit, and his second mixtape, Could 9, two years later. He has also appeared on several albums by famous rappers, including Kayne West, Soulja Boy, Chief Keef, and Fredo Santana.

He has an impressive discography, with 22 mixtapes and albums released over 15 years. His latest album, Life With Louie, was released in 2022.

Juice WRLD

Jared Anthony Higgins got his professional name, Juice WRLD, from the movie Juice, which he interpreted to be about taking over the world. He was born in Chicago in 1998 and grew up in the South Suburbs neighborhood.

He learned to play piano at four years old after his mother enrolled him in lessons. His love for music grew from there, and at 19, he released his first studio album, Goodbye & Good Riddance.

Juice WRLD began experimenting with drugs when he was only 11. Unfortunately, his use of drugs led to his early death, as he suffered a seizure due to oxycodone and codeine intoxication a few days after his 21st birthday.

femdot

Femdot, born Femi Adigun, is relatively new to the Chicago rap scene. He was born in Evanston, Illinois, but grew up in Chicago, where he has made a name for himself since his first album, Delacreme 2, in 2018.

He sets himself apart from other rappers with his subject matter and lyrics, which are slightly more wholesome than others. His music tackles topics such as student loans and cigarettes instead of the prevailing topics of drugs and gang violence.

One of his more recent releases, “94 Camry Music,” has gotten over 16 million listens on Spotify. So, although he’s new, he’s making quite a name for himself.

Lil Bibby

Brandon George Dickinson, or Lil Bibby, was born in 1994 in the South Side neighborhood of Chicago.

Lil Bibby began his rap career in 2011 and released his first mixtape, Free Crack, in 2013, which featured fellow Chicago rappers King Louie and Lil Derb.

In 2017, along with his brother, Lil Bibby started a record label called Grade A Productions, which is credited for discovering Juice WRLD.

Chief Keef

Chief Keef was born in Chicago in 1995. He was named Keith Farelle Cozart after his deceased uncle, who had the nickname “Big Keef,” from which his stage name originated.

After being placed under house arrest in 2011, Chief Keef began posting some of his raps on YouTube. His rap, “I Don’t Like,” caught the attention of some big names, including Kayne West, who remixed it.

After Kayne’s version was released, Chief Keef became famous almost overnight, with record labels engaging in bidding wars over signing him in 2012.

Common

Lonnie Rashid Lynn, better known as Common or Common Sense, was born in 1972 in Chicago’s Hyde Park neighborhood. He began rapping in high school in the late 1980s.

Common has ventured beyond rapping, with acting roles in big productions such as American Gangster and Suicide Squad, as well as several appearances on television shows.

Common has also done modeling and is an avid activist. His most recent album, A Beautiful Revolution Pt. 2, released in 2021, garnered primarily positive reviews.

Mick Jenkins

Although Mick Jenkins was born in Huntsville, Alabama, he is based in Chicago, where he has lived since he was nine.

Jenkins began rapping at open mic nights when he was 17. He released his first mixtape, The Mickstape, in 2012 and his first album, The Healing Component, in 2016. 

Jenkins has been highly active recently, releasing six singles, one EP, and one studio album between 2020 to 2022.

Twista

Twista is the stage name of Carl Terrell Mitchell. He was born in 1973 in the K-Town area of the West Garfield Park neighborhood in West Chicago.

Twista started prepping for his career fairly early, as he began rapping when he was 12. By the time he was 18, he had released his first album, Runnin’ Off at da Mouth, under his original stage name Tung Twista.

Twista is still active today, with his latest album released in 2019.

G Herbo

Herbert Randall Wright III, or G Herbo, was born in 1995 in Chicago. He is close friends with Lil Bibby and has collaborated with him on many songs, including “Kill Shit,” which has gotten over 50 million views on YouTube.

The pair gained even more attention when rapper Drake called their music “the future.” In 2022, G Herbo released Survivor’s Remorse, which reached number 9 on US Billboard 200.

Open Mike Eagle

Michael W. Eagle, better known as Open Mike Eagle, was born in 1980 in Chicago. Along with contemporary rappers Dumbfounded and Psychosiz, Open Mike Eagle started a group named Thirsty Fish and released their first rap album, Testing the Waters, in 2007.

Open Mike Eagle also hosts two podcasts and co-hosts two others. He has an extensive list of guest appearances on other rappers’ albums, television shows, and cartoons.

Vic Mensa

Victor Kwesi Mensah, or Vic Mensa, was born in 1993 in the Hyde Park neighborhood of Chicago. He began his rapping career in 2009, forming the group Kids These Days, which won first place in Congress Theater’s “Next Big Thing” contest.

After the group split up in 2013, Vic Mensa went solo. He featured in one of Kayne West’s songs, “Wolves.” He has released one solo studio album and one collaborative album to date.

Chance the Rapper

Chancelor Johnathan Bennett, known as Chance the rapper or simply Chance, was born in Chicago in 1993. He had a rather different upbringing than most, with his father being an aide for Barack Obama when he was a senator and his mother working for the Illinois Attorney General.

With such parents, Chance the Rapper is heavily involved in activism and politics. In 2020, he was awarded the UNICEF Chicago Humanitarian Award.

While Chance only has one studio album, he has numerous mixtapes and singles, and many other artists have featured him in their work, including Lil Wayne, Skrillex, and Kayne West.

Da Brat

Da Brat, born Shawntae Harris-Dupart in 1974, was born and raised in Chicago. Her career started when she won a local rap contest in 1992.

Da Brat has had two top-ten hits on the Billboard Hot 100 and has collaborated with famous artists such as Lil’ Kim, Missy Elliott, and Mariah Carey.

Besides her musical work, Da Brat has been in six movies and countless television shows.

Polo G

Taurus Tremani Bartlett, or Polo G, was born in 1999 in the Old Town neighborhood of Chicago.

He found success early, with his debut album Die a Legend peaking at number 6 and his second album The Goat peaking at number 2 on the US Billboard 200. He’s also had ten singles chart on the Billboard Hot 100.

His lyrics are known for dealing with sensitive subject matter like drugs and mental health. Polo G has stated his musical influences were Lil Wayne and Tupac Shakar.

Noname

Fatimah Nyeema Warner, known professionally as Noname, was born in 1991 in Chicago. Along with being a rapper, she’s also a poet and record producer.

She began her rapping career in 2010 and became more well-known after appearing on Chance the Rapper’s track “Lost” in 2013.

Noname has one solo album, one mixtape, and five singles released between 2016 and 2021. She’s also made several guest appearances in songs from other rappers, including Chicago rappers Saba and Mick Jenkins.

Fredo Santana

Fredo Santana was born Derrick Coleman in 1990 in Chicago. He was the older cousin of Chief Keef.

He began releasing mixtapes between 2012 and 2013, and his debut album, Trappin’ Ain’t Dead, was released in 2013.

Shortly after the release of his second album, Fredo Krueger 2, Fredo suffered a fatal seizure in early 2018 accredited to his heavy drug use and died at 27.

Saba

Tahj Malik Chandler was born in Chicago in 1994 and adopted the stage name Saba when he began rapping as a teen.

Saba partnered with fellow Chicago Rapper Mick Jenkins in 2012 and released his first mixtape, GETCOMFORTable, in the same year.

Saba has three mixtapes and two studio albums released under his own record label, Saba Pivot, LLC.

Calboy

Calvin Lashon Woods was born in 1999 in Chicago but moved to Calumet City, Illinois, shortly after. He started rapping to express his frustrations at growing up in poverty.

Calboy released his first three mixtapes between 2017 and 2018. Since then, he’s released several EPs and singles.

He credits many Chicago rappers as his influences, including Chance the Rapper, Chief Keef, and G Herbo.

Lil Reese

Tavares Lamont Taylor, known as Lil Reese, was born in 1993 in Chicago. He made a name for himself in the Chicago rap scene after he was featured on Chief Keef’s “I Don’t Like.”

Lil Reese’s popularity grew after he released singles “Us” and “Beef.” In 2012, he remixed “Us” with Drake and Rick Ross, which featured on Rick Ross’ mixtape The Black Bar Mitzvah.

In 2019, Lil Reese was shot in the neck and had critical injuries. A day after being discharged, he released the single “Come Outside” as a message to his attacker.

Joey Purp

Joseph Davis, known as Joey Purp, was born in 1993 in Chicago. He realized he had a knack for freestyling rapping in high school and dropped out in his senior year to pursue a career in rap while supporting himself by working at a clothing store.

Joey Purp released his first mixtape in 2012. His second mixtape, iiiDrops, was released in 2016 and was featured on the year-end lists of publications Complex, Pitchfork, and Rolling Stone.

Famous Dex

Dexter Tiewon Gore Jr., who adopted the stage name Famous Dex, was born in 1993 in New York City. However, he was raised in the Englewood neighborhood of Chicago’s South Side.

Famous Dex decided to pursue a career in music after his mother’s death from breast cancer. He has a pink ribbon face tattoo to commemorate her.

Famous Dex self-released his first three mixtapes before being signed by Rich Forever Music, under which he released nine more.

Earl Sweatshirt

Thebe Neruda Kgositsile, known as Earl Sweatshirt, was born in Chicago in 1994. At 16, he released his first mixtape, Earl, which garnered him critical praise. After its release, his mother sent him to a school for at-risk teens in Samoa, pausing his career.

Earl Sweatshirt returned to the rap scene in 2013 with his debut album Doris. He released three subsequent albums and has been called a “hip-hop prodigy” by many in the music industry.

Montana of 300

Montana of 300, born Walter Anthony Bradford in 1987 in Chicago, released his debut album Fire in the Church on May 20th, 2016. The album peaked at 95 on the Billboard 200. 

Since then, he committed to releasing an album every year on May 20th, though that only lasted three years.

Montana of 300 released his most recent album in 2022 after several delays.

Psalm One

Cristalle Bowen, better known by her stage names Psalm One and Hologram Kizzie, was born in 1980 in the Englewood neighborhood of Chicago.

Her rap career began with the release of her first album, Bio: Chemistry, in 2002. The significance of the album’s name comes from her degree in chemistry from the University of Illinois.

Psalm One has an extensive discography, with 12 albums, three mixtapes, seven EPs, seven singles, and numerous guest appearances.

Rockie Fresh

Known professionally as Rockie Fresh, Donald Howard Pullen was born in 1991 in Chicago. 

His first album, Rockie’s Modern Life, released in 2009, got recognized by some big names in the music industry, including Patrick Stump of Fallout Boy and the Madden brothers of Good Charlotte.

In 2010, he released The Otherside, which had him named one of Metromix’s “Hottest 25 Artists Under 25.” Rockie Fresh is still in the Chicago music scene today, with his last album released in 2021.

Lupe Fiasco

Wasalu Muhammad Jaco, or Lupe Fiasco, was born in 1982 in Chicago. His career began at 18, creating music in his father’s basement. At 19, he joined the group Da Park, which Epic Records later signed.

His rap is noted for its lyrics, which reject the misogyny in hip-hop music.

Apart from being a musician, Lupe Fiasco is also a philanthropist and has many business ventures.

King Von

Dayvon Daquan Bennett, or King Von, was born in Chicago in 1994. At just 14, he went to jail on first-degree and attempted murder charges, though he was later acquitted.

King Von was signed by Lil Durk’s record label and released his hit single “Crazy Story” in 2018.

After releasing an album in 2020, his life and career were cut short after he was shot and killed on November 6 of the same year. His album, What It Means to Be King, was released posthumously in 2022.

Add-2

Andre D'Juan Daniels, better known as Add-2, was born in 1986 in Chicago. The industry recognized his talent for rap after the release of his second mixtape, A Tale of Two’s City: Volume 2, in 2007.

Since his career began, he’s released two solo albums and eight mixtapes. He’s also worked with famous names, including Kendrick Lamar, The Roots, and Gerald Walker.

No I.D.

Ernest Dion Wilson was born in 1971 in Chicago. His stage name, No I.D., is a play on the backward spelling of his middle name.

No I.D. released his first album in 1996 and has mentored many artists, such as Kayne West and J. Cole, earning him the moniker “The Godfather of Chicago Hip Hop.”

No I.D. is also a prominent record producer and is close to holding the title of producing the most Jay-Z tracks, just behind Timbaland and Just Blaze.

Top Chicago Rappers, Final Thoughts

The list of best Chicago rappers is extensive, which is no surprise as the Chicago rap scene has thrived since the 1980s.

Next time you’re in the mood for some solid beats and heavy-hitting lyrics, choose an artist from this list and lose yourself in Chi-Town rap. It may just inspire you to create some raps of your own.