Chicago Rappers

Map of the Top Rappers from Chicago

Long before the success of Chief Keef, the city’s hip hop scene of top Chicago rappers was surprisingly a non-factor, and not nearly close to the size as it is today.

Historically, much smaller cities have had a larger presence in hip hop, but that changed when rappers from Chicago like Chief Keef debuted in 2011 with the hit single, “Don’t Like.”  Following his success, the wave of Chicago rap artists and the Chicago drill movement began, especially through the likes of Chief Keef, King Louie, and the 600 movement leading the way. 

Maybe the most influential, and also the most imitated, culture and lifestyle of our time, Chicago rap music, especially Chicago drill music, not only influenced others to rap and bring the drill sound and content into their music, but also changed the landscape of the streets, from Chicago to just about every city nationwide.

Before today’s wave of Chicago rappers, the only true mainstays of artists were the likes of Kanye West, Common, Twista, Do or Die, Crucial Conflict, Psycho Drama, and several others that were blessed and talented enough to make it onto a national stage. Other well respected rappers from Chicago over the years have included Bump J, Bo Deal, LEP Bogus Boys, and a few more local artists who also paved the way for the younger generation.

Map of Chicago Rappers

The below map of Chicago rappers pinpoints over 90 of the best all-time rap artists from the city of Chicago and the surrounding communities of the Chicagoland area. This included the current top artists of the 2020s, highlighted in black, and many of the legends, pioneers, and decease performers from the 2010s, 2000s, and 1990s highlighted in red.

*Make sure to Leave a Comment, if any artists are missing or in the wrong location 

Today’s Top Chicago Rap Artists

Fast-forwarding to the present day, Chicago rap artists have become some of the world’s top rap stars, rappers like Lil Durk, Chief Keef, Polo G, G Herbo, and Chance The Rapper.  Unfortunately, a problem that has plagued the local hip hop scene has been the amount of deaths and incarcerations of key artists. Artists that have been at the forefront of today’s generation of Chicago rappers, like LA Capone, King Von, FBG Duck, and too many more to name.

Despite the tragedies, Chicago rap music is a world leader and still has enough momentum to be considered as one of the top hip hop markets. Today, the city offers a wide variety of hip-hop for today’s music. From lyrical artists, like Lucki, to leading women in hip-hop, like Queen Key, Dreezy, and Lady XO. To the various soulful and meaningful hip-hop artists, like Mick Jenkins, Saba Pivot, and Vic Mensa, to artists who are able to adapt to any situation and combine elements of street and trap music with the realities of life, like Lil Zay Osama, KB Mike, PGF Nuk, and Booka600.

Top 20 Chicago Rappers

1. Kanye West

Kanye West’s, a global icon, influence spans production, artistry, fashion, and pop culture. His career took off in the early 2000s as a producer with Roc-A-Fella before releasing his debut album, The College Dropout in 2004. Hits like “Gold Digger,” “Stronger,” and “Heartless” are just a few that stand out in his extensive discography, which includes critically acclaimed albums like Late Registration, Graduation, and My Beautiful Dark Twisted Fantasy.

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2. Lil Durk

Durk burst onto the Chicago rap scene with his mixtape series Signed to the Streets during the mid-2010s, which brought him to the top Chicago drill and among the next generation of hip hop artists. Over the years, Lil Durk has released multiple chart-topping albums, such as Remember My Name (2015) and The Voice (2020). Songs like “Laugh Now Cry Later,” a collaboration with Drake, “All My Life” with J Cole, “When We Shoot,” “Broadway Girls,” “Backdoor,” are among his most popular tracks, showcasing his versatility and mainstream appeal.

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3. Polo G

Hailing from Chicago’s North Side, out of the notorious Marshall Fields apartments, Polo G emerged with his deep, melodic take on drill music. His debut album Die a Legend (2019) skyrocketed him to fame, especially with the hit track “Pop Out,” earning him a place on the Billboard charts and a platinum certification. His following albums, The Goat (2020) and Hall of Fame (2021), only further cemented his status in the industry.

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4. Chance The Rapper

Chance The Rapper has been an independent trailblazer in the music world since his second mixtape, Acid Rap, dropped in 2013 and became a digital sensation. In 2016, he won three Grammy Awards for his streaming-only album Coloring Book. Chance’s upbeat fusion of sounds, alongside being one of Chicago’s most talented and creative artists, sets him apart in the hip-hop scene.

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5. G Herbo

Hailing from Chicago’s East Side, G Herbo’s raw and unflinching lyrical content draws directly from his experiences growing up in a community once known as Terror Town. While beginning during the early 2010s as Lil Herb, his growth has been witnessed on albums like Humble Beast (2017) and PTSD (2020). His talent as once of the top Chicago rappers perfectly showcases his ability to paint a picture of the streets of America.

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6. Chief Keef

A man that many Chicago rappers need to thank, Chief Keef is often credited as a pioneer of Chicago’s drill music scene, which gained popularity in the early 2010s. Keef’s raw and gritty raps about the streets of Chicago propelled him to fame when he was just a teenager. His debut album Finally Rich in 2012 included hits like “I Don’t Like” and “Love Sosa,” which have become anthems among Drill fans.

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7. King Von

King Von was a rising star in the drill music scene with a style that vividly depicted the street life of Chicago. He rose to fame with his single “Crazy Story,” which became a Chicago drill anthem. His 2020 album Welcome to O’Block continued to showcase his storytelling abilities and further solidified his status as one of the promising new voices in rap. Tragically, King Von’s rising career was cut short, but he left behind a legacy of music that painted a compelling picture of growing up in Parkway Gardens (O-Block).

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8. Lucki

Lucki first gained attention with his project Alternative Trap in 2013. His music diverges from the traditional drill sound of other Chicago rappers, wielding a more experimental and psychedelic approach to hip-hop. With a laid-back flow and confessional lyrics, Lucki has carved out a niche for himself in hip-hop with a loyal fan base through albums and EPs like Days B4 III (2019), s*x m*ney dr*gs (2023), Freewave 3 (2019).

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9. CalBoy

CalBoy was part of the fresh wave of rappers from Chicago who found success. His melodic style blends elements of drill with a more soulful and emotional delivery, which can be heard in his breakout hit “Envy Me.” The song surged in popularity in 2018, leading to his EP Wildboy in 2019 that featured collaborations with established artists like Meek Mill and Lil Durk.

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10. Vic Mensa

Vic Mensa is known for his eclectic style which merges hip-hop with elements of rock and electronic music. His time with the group Kids These Days paved the way for his solo endeavors, including his acclaimed mixtape Innanetape in 2013. Vic Mensa’s fearless social commentary sets him apart, as showcased in his debut projects, like There’s Alot Going On in 2016 and The Autobiography in 2017.

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11. Saba Pivot

Saba Pivot is one of the most prolific Chicago rappers as he hails from Chicago’s West Side. Notable for his soulful vibes, he started gaining traction early in his career following the 2014 mixtape ComfortZone. He made his way into the limelight with his sophomore album, Care for Me, released in 2018, which established him as a rising star in the hip-hop scene.

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12. Mick Jenkins

Mick Jenkins, a South Side Chicago native, is known for his cerebral approach to hip-hop . He first broke onto the scene with his mixtape The Waters in 2014, which quickly became one of the best hip-hop projects of the year. Through his career, Mick has earned a reputation for his poetic approach and his ability to navigate complex beats with ease. His debut album The Healing Component (2016) and songs like “Jazz” stands out as some of his most notable works.

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13. Noname

Noname is a poet-turned-rapper known for story-rich music. She debuted with the release of her mixtape Telefone in 2016. Her follow-up project, Room 25, released in 2018, received similar acclaim and showcased her growth as an artist. Noname’s voice has a unique and mellow tone, which when combined with her reflective style, captures the listener’s attention, prompting them to hang onto every word.

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14. Lil Zay Osama

Lil Zay Osama is another drill rapper whose raw and intense music reflects life on the streets of the South Side. He entered music in the late 2010s with tracks that embodied the grit and energy of Chicago’s drill scene. With hits such as “Changed Up” and “Survive,” Lil Zay Osama has crafted a discography that resonates with many looking for authenticity in rappers from Chicago.

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15. PGF Nuk

PGF Nuk is another emerging talent, embracing the drill style that has become synonymous with the city’s street culture. Though relatively new to the broader audience, Nuk has made waves of late. Standing for “Pooh Gang Family,” PGF is a testament to his roots and loyalty to his group. Songs like “Waddup” have solidified PGF Nuk as a name to watch in Chicago’s rap scene.

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16. Dreezy

Dreezy is a multifaceted artist who is a singer and a rapper. She debuted with her mixtape Schizo in 2014 and immediately stamped her presence in the hip-hop and R&B world. Dreezy’s following release, the EP From Now On in 2015, showcased her versatility across various genres. But it was with her 2016 debut studio album, No Hard Feelings, that she scored her breakthrough. The album featured the platinum single “Body,” featuring Jeremih, which climbed the charts.

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17. Booka600

Booka600 is an artist ingrained in the fabric of Chicago’s drill music scene. His reflective lyrics and melodic approach to the genre have set him apart from Chicago rappers. With strong affiliations to the OTF (Only The Family) collective led by fellow Chicago rapper Lil Durk, Booka600 has had ample opportunity to develop his style and presence, especially with projects like Word to LA and tracks like “War Scars.”

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18. Lil Reese

Lil Reese, a pivotal figure in the Chicago drill music scene, surged to fame after featuring on Chief Keef’s hit “I Don’t Like” in 2012. His gritty narratives and unflinching portrayal of the streets helped him establish himself as the face of Chicago’s drill scene. Reese’s debut mixtape, Don’t Like, further solidified his place in the rap genre.

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19. BigKayBeezy

BigKayBeezy is a rising star in the Chicago rap scene, known for his hard-hitting tracks. Introduced into the music landscape during the late 2010s, BigKayBeezy’s music often reflects the griminess of the Chicago streets, a theme that is prevalent throughout his discography, including projects such as Bad Intentions or GG4L. Some of his most popular tracks are “Bookbag 2.0,” featuring Polo G, “Walk Down,” with Pooh Shiesty, “Bookbag,” and “Touchdown.”

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20. KB Mike

KB Mike’s music is deeply rooted into storytelling and emotional vulnerability. The heartfelt nature of his songwriting is evident in tracks like “Revenge 2,” “Deep In Love,” “Thru Worse N Thru Better,” “Toxic Love,” and “Used To.” His music often resonates with audiences drawn to his relatable narratives and melodic style. KB Mike entered the music scene intending to provide an outlet for his life experiences, blending elements of hip-hop and R&B to create a sound of his own.

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Top Rappers from Chicago Related Topics:

1 Map of Chicago Hoods

2 Top 10 Chicago R&B Artists

3 Top 30 Chicago Music Artists of All-Time

4 Top 25 Atlanta Rappers

5 Top 100 Female Rappers

6 Top 25 New York City Rappers

*Unofficial Order. The more popular artists that have a combination of the most followers, streams, views, and most recent releases are near the top.

*If any artists are missing from the list email info@kltvltz.com