Top 25 Chicago rappers you should watch out in 2024

Top 25 Chicago rappers you should watch out in 2024

"Music, once admitted to the soul, becomes a sort of spirit, and never dies." This quote might explain why people sometimes lose themselves to those beats. The different genres considered, it is a case of pick your poison, among them being rap music. Originally from New York City in the 1970s, rap music has grown worldwide. How many rappers from different regions can you name? Here are some top Chicago rappers you should watch out for in 2024.

From left to right is Chief Keef,Juice Wrld and Da Brat
Chicago rap music is called Drill, a subgenre of Hip-hop music that originated in Chicago. Photo: Bennett Raglin, Amy Sussman, Terence Rushin (modified by author)
Source: UGC

TABLE OF CONTENTS

Chicago has been known to provide some of the finest rappers, with popular mainstays like Kanye West dominating the field and even making it to the international stage. Many have continued to come up, while others are breaking a sweat to reach higher levels.

This ranking of the most famous Chicago rappers is based on a combination of factors, including artists' impact on the genre, critical acclaim and commercial success. Note that the popularity and recognition of artists are subject to change. Some artists are now dead, but their legacy lives on through their music.

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Who is the best Chicago rapper?

RankName
1Kanye West
2King Von
3Earl Sweatshirt
4Chief Keef
5Polo G
6Common
7Juice Wrld
8G Herbo
9Lil Bibby
10Saba Pivot
11Lil Durk
12Chance the Rapper
13Taylor Bennett
14King Louie
15Lil Reese
16Twista
17Lupe Fiasco
18Kami
19Noname
20Da Brat
21Add-2
22Queen Key
23Jeremih
24Montana of 300
25Mick Jenkins

Top 25 Chicago rappers in 2024

Rap music comes in many subgenres, including but not limited to old school, jazz rap, trap, gangsta rap, bounce, and rap rock, amongst others. Chicago rap music is called Drill, a subgenre of hip-hop music that originated in Chicago.

1. Kanye West

Kanye West aka Ye is seen in Los Angeles, California.
Kanye West aka Ye is seen in Los Angeles, California. Photo: MEGA
Source: Getty Images
  • Full name: Kanye Omari West
  • Date of birth: 8 June 1977
  • Age: 46 years old (as of 2024)

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You cannot talk about Chicago's best rappers and fail to mention Kanye West. Heb became a worldwide hitmaker and has produced for artists like Jay-Z. He has also won multiple Grammy Awards. His album The College Dropout became a hit that saw his name take up space in the best rappers list.

2. King Von

King Von attends Compound Saturday Nights at Compound in Atlanta
Rapper King Von attends Compound Saturday Nights at Compound in Atlanta, Georgia.Photo: Prince Williams
Source: Getty Images
  • Full name: Dayvon Daquan Bennett
  • Date of birth: 9 August 1994
  • Died: 6 November 2020 (age 26 years)

Unfortunately, not all great Chicago artists rappers have maximised their full potential due to early deaths. Owing to the fact that some subgenres are associated with crime, for example the Drill genre.

King Von is one of the Chicago drill rappers whose life was cut short following a shooting. Some of his best-performing hits were Crazy Story and Took her to the O. King Von continued to make hit songs and mixtapes before he met his death on 6 November 2020.

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3. Earl Sweatshirt

Earl Sweatshirt performs during BUKU Music + Art Project
Earl Sweatshirt performs during BUKU Music + Art Project at Mardi Gras World in New Orleans, Louisiana. Photo: Erika Goldring
Source: Getty Images
  • Full name: Thebe Neruda Kgositsile
  • Date of birth: 24 February 1994
  • Age: 30 years old (as of 2024)

Earl Sweatshirt is an American rapper, songwriter, record producer, and occasional actor. He is a member of the hip hop collective Odd Future. Earl Sweatshirt has released five studio albums, such as Doris, Some Rap Songs, Sick! and Voir Dire. Earl Sweatshirt has also released several EPs, including Earl and Solace.

4. Chief Keef

Chief Keef attends the BET Awards 2023 at Microsoft Theater
Chief Keef attends the BET Awards 2023 at Microsoft Theater in Los Angeles, California. Photo: Bennett Raglin
Source: Getty Images
  • Full name: Keith Farrelle Cozart
  • Date of birth: 15 August 1995
  • Age: 28 years old (as of 2024)

Keef grew up in the south side of Chicago, where his career was birthed. He is one of the Chicago drill rappers who managed to gain popularity at an early age. Chief Keef became famous through his mixtapes tapes in 2012 and has become a fully-fledged rapper. Among his best hits is Love Sosa, and I don’t like.

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5. Polo G

Polo G attends Amazon Music Live Concert Series in Los Angeles
Polo G attends Amazon Music Live Concert Series in Los Angeles, California. Photo: Jerritt Clark
Source: Getty Images
  • Full name: Taurus Tremani Bartlett
  • Date of birth: 6 January 1999
  • Age: 25 years old (as of 2024)

Rapper Polo G is one of the of the O block Chicago rappers who made an appearance on King Von’s album shortly before he met his death. Polo G rose to prominence following the release of his singles Finer things and Pop out. His second studio album, The Goat, released in 2020, peaked at number 2 on The Billboard 200.

6. Common

Common performs onstage during Souls To The Polls Drive-In Rally
Common performs onstage during Souls To The Polls Drive-In Rally for Rev. Raphael Warnock at Riverside EpiCenter in Austell, Georgia. Photo: Paras Griffin
Source: Getty Images
  • Full name: Lonnie Rashid Lynn
  • Date of birth: 3 March 1972
  • Age: 51 years old (as of 2024)

Formerly known as Common Sense, Lonnie Rashid Lynn debuted with the album Can I borrow a dollar in 1992. In 2003, Common won a Grammy Award for the best R&B song; in 2005, his album Be, was nominated for Best Rap Album.

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His other albums include A Beautiful Revolution (Pt. 1), A Beautiful Revolution (Pt. 2), Let Love, Black America Again and Nobody's Smiling.

7. Juice Wrld

Juice Wrld poses with the award for Best New Artist
Juice Wrld poses with the award for Best New Artist in the press room during the 2019 Billboard Music Awards at MGM Grand Garden Arena in Las Vegas, Nevada. Photo: Amy Sussman
Source: Getty Images
  • Full name: Jarad Anthony Higgins
  • Date of birth: 2 December 1998
  • Died: 8 December 2019 (age 21 years)

Juice Wrld was one of the trap music Chicago rappers who met their death early in their career. He was labelled a hip-hop, emo rap, trap and Soundcloud rap artist.

He released a song- Rikers, featuring Drake, amongst other hit songs. Rapper Juice Wrld also worked with Polo G on Trippie Red, Bennie Blanco on Graduation, Marshmello on Come & go, and Halsey on Life’s a mess.

8. G Herbo

G Herbo speaks onstage during the BET Awards
G Herbo speaks onstage during the BET Awards 2023 at Microsoft Theater in Los Angeles, California. Photo: Paras Griffin
Source: Getty Images
  • Full name: Herbert Randall Wright III
  • Date of birth: 8 October 1995
  • Age: 28 years old (as of 2024)

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G is an American rapper and songwriter best known for his album Swervo. Together with Lil Bibby, they released the album which led them to gain fame. The song has since then accumulated more than 50 million views.

At some point, Drake referred to the duo as ‘the future of hip hop’, and their popularity hit the fan. G Herbo has produced and released other hit songs like Lord Knows, Take Me Away, and I like to name a few.

9. Lil Bibby

Lil Bibby poses backstage at Spotify's RapCaviar Live
Lil Bibby poses backstage at Spotify's RapCaviar Live in Chicago at Aragon Ballroom in Chicago, Illinois. Photo: Timothy Hiatt
Source: Getty Images
  • Full name: Brandon George Dickinson
  • Date of birth: 18 July 1994
  • Age: 29 years old (as of 2024)

Lil Bibby is a rapper and record executive who has done impressive work. His popularity in America rose through his songs and music. Lil Bibby has worked with Juice Wrld and Kid Laroi. Some of his singles include How We Move, Tired of Talkin, Dead or in Prison and Complicated.

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10. Saba Pivot

  • Full name: Tahj Malik Chandler
  • Date of birth: July 17, 1994
  • Age: 29 years old (as of 2024)

Saba Pivot is a Chicago-based rapper and record producer. He gained recognition after releasing his two independent mixtapes in 2012 and 2014. He has also been featured in Chance rappers’ mixed tape Acid Rap.

He has had a couple of releases, his latest being his third album, Few Good Things, on 4th February 2022. Saba Pivot has featured other Chicago rappers like G Herbo, Krayzie Bone, Allen Kane and Pivot Gang. The song rose to position 44 on US independent albums in 2022.

11. Lil Durk

Lil Durk performs during iHeart Powerhouse 105.1
Lil Durk performs during iHeart Powerhouse 105.1 at Prudential Center in Newark, New Jersey. Photo: Michael Loccisano
Source: Getty Images
  • Full name: Durk Derrick Banks
  • Date of birth: 19 October 1992
  • Age: 31 years old (as of 2024)

His top tracks include What Happened to Virgil ft Gunna, Mad Max, Who want Smoke ft G Herbo, & 21 Savage, Broadway Girls featuring Morgan Wallen, among others. Lil Durk's latest release include Smurk Carter, Guitar in My Room and All My Life.

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12. Chance the Rapper

Chance the Rapper speaks during the 50th Anniversary Of Hip Hop keynote
Chance the Rapper speaks during the '50th Anniversary Of Hip Hop' keynote at SXSW Sydney in Sydney, Australia. Photo: Brendon Thorne
Source: Getty Images
  • Full name: Chancelor Johnathan Bennett
  • Date of birth: 16 April 1993
  • Age: 30 years old (as of 2024)

The Holy hitmaker is known for releasing mixtapes such as Acid Rap and Coloring Book, which received a Grammy Award for Best Rap Album and a BET for Best Mixtape. Chance the Rapper has collaborated with famous faces like Kanye West, Justin Beiber and Lil Wayne.

13. Taylor Bennett

  • Full name: Taylor Matthew Bennett
  • Date of birth: 19 January 1996
  • Age: 28 years old (as of 2024)

Taylor has been stealing the show with his unique lyrical style, flow and live performances. In 2013, Taylor Bennett received recognition for his self-released mixtape, The Taylor Bennett show.

He has released two more mix tapes- Mainstream music—the restoration of an American Idol and a collaboration with his older brother Chance the Rapper.

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14. King Louie

Music producer King Louie attends Highline Ballroom
Music producer King Louie attends Highline Ballroom in New York City. Photo: Johnny Nunez
Source: Getty Images
  • Full name: Louis King Johnson, Jr.
  • Date of birth: 27 December 1987
  • Age: 36 years old (as of 2024)

King Louie is one of the first artists to bring Chicago’s drill music to an international audience. In 2015, he came close to making the list of Chicago rappers killed by gun violence after being shot in the head and chest.

Fortunately, King Louie survived and has since released Live and Die in Chicago, one of his best-performing tracks. The hit paints a picture of the socioeconomic struggles and violence in Chicago.

15. Lil Reese

  • Full name: Tavares Lamont Taylor
  • Date of birth: 6 January 1993
  • Age: 31 years old (as of 2024)

Since his debut mixtape, Don't like Lil Reese has released six more mixtapes, including Super Vultures, a collaborative project with Lil Durk. Being featured in Chief Keef's I Don't like, gained him international recognition and received popularity through his music videos Us and Beef.

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In 2013, Lil Reese released his second solo mixtape featuring Chief Keef, Lil Durk, Fredo Santana, Waka Flocka and Wales as guest appearances.

16. Twista

Twista attends the 2 Chainz Hosts NBA All-Star Def Jam End Party
Twista attends the 2 Chainz Hosts NBA All-Star Def Jam End Party at Milk Studios in Los Angeles, California. Photo: Johnny Nunez
Source: Getty Images
  • Full name: Carl Terrell Mitchell
  • Date of birth: 27 November 1973
  • Age: 50 years old (as of 2024)

Twista is an American rapper who made a name for himself by breaking the world record for the fastest rapper. He surpassed Eminem’s record by a few syllables per second.

His song, Mista Tung Twista, is his fastest song on record, where he sings 1,287 words in 4 minutes and 36 seconds. Twista's songs include Overnight Celebrity, Sunshine, Glock, and Prayer, among others.

17. Lupe Fiasco

Lupe Fiasco poses for photos at the drivers meeting in the Chicago Stock Exchange
Lupe Fiasco at the drivers meeting in the Chicago Stock Exchange Trading Room at the Art Institute of Chicago prior to the NASCAR Cup Series Grant Park 220 in Chicago, Illinois. Photo: Michael Reaves
Source: Getty Images
  • Full name: Wasalu Muhammad Jaco
  • Date of birth: 16 February 1982
  • Age: 42 years old (as of 2024)

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Famous for his hit songs Daydreamin’, Suspersatr, I gotcha, and Lamborghini Angles amongst others, Lupe fiasco uses alternative rap and Midwest rap as his rap styles. He has collaborated with Farel, Williams, Jill Scot, Ed Sheeran, and Snoop Dogg, among others.

18. Kami

  • Full name: Kene Ekwunife
  • Date of birth: 5 January 1993
  • Age: 31 years old (as of 2024)

Kami is among the founding members of Savemoney. He released his debut mixtape, Light in 2012. Rapper Kami has since released several singles such as Go Gentle, Reboot, Scene Girl, Home Movies and Foundation.

19. Noname

Noname perform at Circolo Magnolia
Noname perform at Circolo Magnolia in Milan, Italy. Photo: Francesco Prandoni
Source: Getty Images
  • Full name: Fatimah Nyeema Warner
  • Date of birth: 18 September 1991
  • Age: 32 years old (as of 2024)

Noname began rapping in 2010 and later received wide attention when she appeared in the track Lost. She released her debut album, Room 25 in 2018. Some of her singles include Häagen Dazs, Sing 33 and Rainforest. Apart from rapping, Noname is also a record producer and poet.

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20. Da Brat

Da Brat performs onstage during the BET Hip Hop Awards
Da Brat performs onstage during the BET Hip Hop Awards 2023 at Cobb Energy Performing Arts Center in Atlanta, Georgia. Photo: Terence Rushin
Source: Getty Images
  • Full name: Shawntae Harris-Dupart
  • Date of birth: 14 April 1974
  • Age: 49 years old (as of 2024)

Brat is a talented American singer who was raised in two different households. Her parents never married. Da Brat began her music career in 1992 when she won the grand prize in a local rap contest sponsored by Yo! MTV Raps.

Two years later, Da Brat released her fist album Funkdafied. She has since released numerous albums and singles. She has also appeared in films and TV series such as The Real Housewives of Atlanta, Ladies First: A Story of Women in Hip-Hop and Married to Medicine.

21. Add-2

  • Full name: Andre D'Juan Daniels
  • Date of birth: 31 March 1986
  • Age: 37 years old (as of 2024)

Add-2 gained popularity after releasing his second mixtape, A Tale of Two's City: Volume 2. Add-2 had a song, Luxury, featured on MTV and VH1. He has collaborated with renowned artists like 9th Wonder, Kendrick Lamar, The Roots, and Gerald Walker.

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22. Queen Key

  • Full name: Ke'Asha McClure
  • Date of birth: 6 June 1996
  • Age: 27 years old (as of 2024)

Queen Key is an American rapper and songwriter. She is known for her singles such as Hit A Lic, Take Money and Calling All Eaters. Besides her music career, Queen Key is also a mother of three kids who are triplets named Krown, Kash, and Kreative.

23. Jeremih

Jeremih performs on stage during 50 Cent The Final Lap Tour
Jeremih performs on stage during 50 Cent The Final Lap Tour 2023 at Toyota Center in Houston, Texas. Photo: Marcus Ingram
Source: Getty Images
  • Full name: Jeremy Phillip Felton
  • Date of birth: July 17, 1987
  • Age: 36 years old (as of 2024)

Jeremih is an American singer, songwriter and record producer. He gained fame after his first single. Rapper Jeremih cited Michael Jackson, Stevie Wonder, and R. Kelly as his biggest influences.

24. Montana of 300

  • Full name: Walter Anthony "Tony" Bradford,
  • Date of birth: 3 March 1989
  • Age: 34 years old (as of 2024)

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Montana is a talented rapper, singer and songwriter. He began rapping at 15 and grew up listening to great singers like Tupac, Lil Wayne and Jay-Z. He released his first studio album, Fire in the Church, in 2016.

Since then, Montana of 300 has released several other albums like Don't Doubt the God, Pray for the Devil, A Gun in the Teachers Desk, Views from the General's Helmet and Rap God. The singer also appeared in an episode of Empire in 2015 and The Quads.

25. Mick Jenkins

Mick Jenkins performs at the 30th Anniversary of Lollapalooza
Mick Jenkins performs at the 30th Anniversary of Lollapalooza at Grant Park in Chicago, Illinois. Photo: Josh Brasted
Source: Getty Images
  • Full name: Jayson Mick Jenkins
  • Date of birth: 16 April 1991
  • Age: 32 years old (as of 2024)

Mick moved to Chicago, Illinois with his mother and sister when he was nine years old. His passion for music was influenced after he joined a rap competition that he did not win. Mick Jenkins began by releasing several mixtapes and later debuted his album The Healing Component in 2016. He has since released other albums, singles and EPs.

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Who is Chicago's best conscious rapper?

Lucki Camel Jr., better known as Lucki, is labelled Chicago's best-conscious rapper. He is regarded as an influential figure in underground hip-hop.

What rapper came from Chicago?

Some of the popular rappers that were born in Chicago include Kanye West, King Von, Common, Polo G, Juice Wrld, Lil Bibby, Saba Pivot and Chance the Rapper.

Who is the best rapper in Chicago in 2024?

Some of the best rappers in 2024 doing great include Lil Drunk, Chance The Rapper, G Herbo and Mick Jenkins.

The music industry has continued to grow as artists find new ways to capture the hearts and following of their fans. Chicago rappers have managed to garner diehard fans since the days of their all-time big artists, and their creativity and style has continued to evolve and improve.

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