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Chicago has a vibrant hip hop scene with a rich history of talented rappers. The city is known for pioneering new hip hop styles like drill music. Chicago rappers often reflect the city’s gritty streets in their lyrics. From pioneers like Common and Twista to today’s stars like Chief Keef and Chance the Rapper, Chicago rappers have made an indelible mark on hip hop.

The early days of Chicago rap featured pioneering groups like Crucial Conflict and Do or Die. Southside natives, they introduced the world to Chicago’s double time rap style. Chicago rappers like Common and Rhymefest repped conscious rap in the 90s. Common especially became one of the first Chicago rappers to gain national fame. His classic album Be launched his storied career.

In the 2000s, Kanye West exploded onto the scene. His album The College Dropout was an instant classic, mixing rap and soul. Kanye became one of the most famous rappers ever out of Chicago. Veteran Twista, known for his supersonic rapping speed, finally broke through to mainstream success in the 2000s. The decade also spawned hardcore rappers like Shawnna, King Louie, and G Herbo.

In the early 2010s, a new style called drill music emerged from Chicago. Drill combined dark, gritty lyrics with hard-hitting production. Leading the way was Chief Keef, who became a viral sensation with hits like “I Don’t Like.” Fellow drill rappers Lil Durk, Lil Reese, Fredo Santana, and Lil Bibby also found success. Unfortunately, many of these young rappers became embroiled in Chicago gang disputes.

Today, the Chicago rap scene continues to thrive, despite the tragic losses of rappers like Fredo Santana and King Von. Chance the Rapper has become one of the most popular rappers in the world. His 2016 mixtape Coloring Book was the first streaming-only album to win a Grammy. Vic Mensa, Noname, Saba, and Mick Jenkins are other conscious rappers making waves. Polo G, Juice WRLD, Calboy, and Lil Zay Osama are also huge rising talents. Drill rappers like King Von, G Herbo, and Lil Durk remain influential. There’s also a thriving underground scene featuring rappers like Jean Deaux and KC Mike. The future is bright for Chicago hip hop.

Here We Go! Explore The Top 41 Chicago Rappers

chicago rappers

Below rappers from Chicago are set Alphabatical in ascending orders and numbers in descending orders.

41. BigKayBeezy

BigKayBeezy rappers

BigKayBeezy is a rapper from Chicago’s East Side who first started gaining attention in the early 2010s. He got his start releasing mixtapes like S. Beezy and RNS before dropping his debut album Strapped in 2016. BigKayBeezy is known for his deep voice and melodic style of rapping and singing. He often incorporates humor into his lyrics. BigKayBeezy has collaborated with other Chicago rappers like Lil Durk and G Herbo. After dealing with label issues that delayed his career, BigKayBeezy has rebounded in recent years, releasing acclaimed projects like 2020’s Re Up. He continues to be an influential figure in the Chicago rap scene.

40. Booka600

Booka600 rappers

Booka600 is a drill rapper affiliated with the Black Disciples gang who got his start in music as part of the rap collective 600. Booka600 released his first mixtape in 2013, signed to famous producer Lil Bibby’s label. He is known for his gritty, hood lyrics about growing up on Chicago’s dangerous streets. Booka600 has collaborated with many big-name drill rappers like 600 labelmate Lil Durk. However, he has also tried to promote a more positive message to Chicago youth. Following his mixtape Outchea in 2017, Booka600 has continued to release music independently and remains closely tied to Chicago’s drill scene.

39. Chance The Rapper

Chance The Rapper

Chance the Rapper is undoubtedly one of the most influential and popular rappers to come out of Chicago’s hip hop scene. Born Chancelor Bennett in 1993, Chance burst onto the scene as a teenager with his mixtape 10 Day in 2012. He solidified his status with 2013’s Acid Rap and became a global superstar following the Grammy-winning Coloring Book in 2016. Chance’s style features soulful melodies, jazz influences, and positive lyrics centered on faith and activism. He helped pioneer the indie hip hop movement, staying independent and not signing with a label. Chance has pushed Chicago’s sound across the world, collaborating with artists from Ed Sheeran to Madonna. He remains deeply involved in Chicago, doing charity and empowerment work for youth.

38. Chief Keef

Chief Keef

Chief Keef is credited with pioneering Chicago’s gritty drill music style. Born Keith Cozart on the South Side in 1995, he exploded as a teen with viral hits like “I Don’t Like.” Chief Keef’s savage lyrics and raw production encapsulated gang life in Chicago. Though controversial for promoting violence, he became a rap superstar. Chief Keef signed a major label deal and has collaborated with Kanye West, Gucci Mane, and others. However, legal troubles have dogged his career. His influence is still felt through Chicago’s drill scene and his protégés Lil Durk and the late King Von. Love him or hate him, Chief Keef changed Chicago rap forever with drill music.

37. Common

Common rappers

Common is a legendary Chicago rapper who has been active since the 90s. Born Lonnie Rashid Lynn, Jr., Common debuted in 1992 with the album Can I Borrow A Dollar? He gained renown with classic albums like Resurrection and Be, praised for his poetic conscious rap style. Common reached a wider audience through collaborations with artists like Kanye West. He’s also had a successful acting career in movies like Smokin Aces. After over 25 years in rap, Common continues to release acclaimed albums, most recently 2018’s Black America Again. The rappers Common has worked with and inspired reads like a who’s who of hip hop. He’ll forever be remembered as one of Chicago’s finest MCs.

36. Crucial Conflict

Crucial Conflict rappers

Crucial Conflict was one of Chicago’s pioneering rap groups in the mid 90s. With their double time rap flow, they were one of the innovators of what became known as the “Chicago bounce” hip hop style. The group’s 1996 debut album The Final Tic was a big underground hit and led to a deal with Universal Records. Crucial Conflict released the successful Ride The Rhythm album in 1998 featuring their hit song “Scummy.” Group in-fighting led to their breakup in the early 2000s, but they later reconciled. Crucial Conflict hasn’t released an album since 2004, but they remain influential on Chicago rap to this day. Their fast-paced party raps can be heard in modern drill music.

35. Da Brat

Da Brat rappres

Chicago native Da Brat became one of the first commercially successful female rappers in the 1990s. Born Shawntae Harris in 1974, she got her start opening for Kris Kross before releasing her debut Funkdafied in 1994. Da Brat stood out with her tomboy style and hardcore lyrics. Hits like “Give It 2 You” made her a platinum-selling, Grammy-nominated rapper. Legal issues derailed her career in the 2000s, but she continues to appear as a featured artist. These days she often collaborates with Chicago’s new generation of rapper. Over 25 years since her debut, Da Brat’s longevity proves her pioneer status.

34. DCG Brothers

DCG Brothers rappers

The DCG Brothers were an influential duo from Chicago’s early 90s underground rap scene. Rappers Maestro and Don C creatively explored social issues in their jazzy, distinctive style. The DCG Brothers were known for their positive Afrocentric lyricism and experimentation. They collaborated with acts like A Tribe Called Quest before disbanding. Though their output was limited, the DCG Brothers are considered pioneers who inspired future Chicago rappers to embrace their creativity. Maestro went on to a long solo career, remaining dedicated to uplifting African American culture before passing away in 2018.

33. Do or Die

Do or Die rappers

Do or Die is a rap group that helped put Chicago’s “bounce” rap style on the map in the 90s. The trio of AK, Belo Zero, and Nard came up under Chicago rapper Twista. Do or Die released their hit single “Po Pimp” in 1996, which introduced the world to their slick, fast-paced flow. Their album Picture This went gold and is considered a classic Chicago rap album. Legal issues derailed Do or Die in the 2000s, but some original members still perform using the group’s name. They never matched their early success, but Do or Die helped establish Chicago as a hotbed for rapid-fire lyricists.

32. Dreezy

Dreezy rappers

Dreezy is a popular female rapper representing Chicago’s new school. Born Seandrea Sledge in 1994, she first made waves in 2014 with her mixtape Schizo. Dreezy gained more buzz with “We Gon’ Ride” featuring Gucci Mane. Her album No Hard Feelings followed in 2016 to critical acclaim. Dreezy’s confident rhymes and singing ability have led to collaborations with everyone from T-Pain to Jacquees. She’s continued releasing acclaimed projects like Big Dreez. Currently signed to Interscope, Dreezy has said her mission is to show there are no limitations to being a female rapper in Chicago’s male-dominated scene.

31. Earl Sweatshirt

Earl Sweatshirt

Earl Sweatshirt is an alternative hip hop artist originally from Chicago. Born Thebe Neruda Kgositsile in 1994, Earl gained fame with the rap collective Odd Future as a teen. His debut mixtape Earl showcased clever, controversial lyrics exploring dark themes. However, he disappeared from music for two years due to getting sent to rehab. Earl’s made his comeback with critically acclaimed albums like Some Rap Songs. Now more introspective, he moved from LA back to his native Chicago in 2020. Earl Sweatshirt remains one of the city’s most unique talents, crafting a hypnotic, experimental style of underground rap.

30. Fredo Santana

Fredo Santana rappers

Fredo Santana was a popular rapper who emerged from Chicago’s drill scene. Struggling with addiction and mental health issues, Fredo died from a seizure in 2018. Born Derrick Coleman in 1990, he started rapping with his cousin Chief Keef before releasing his own Savage Life mixtape in 2013. Fredo Santana’s gruff voice and uncompromising lyricism defined drill music’s harsh mentality. Songs like “Jealous” and “Rings” made him a local star in Chicago’s rap scene. He collaborated with artists like Kendrick Lamar before his untimely passing. Though only active for five years, Fredo Santana left an impact on Chicago hip hop.

29. G Herbo

G Herbo rappers

G Herbo has become one of Chicago’s most popular drill rappers in recent years. Initially going by Lil Herb, he got started rapping as a teen in the early 2010s. G Herbo first gained attention for his collaborations with fellow Chicago rappers like Lil Durk and Chance the Rapper. His mixtapes like Welcome to Fazoland and Pistol P Project showcased his talent for storytelling about street life in Chicago. G Herbo has successfully crossed over to a major label, releasing the albums Humble Beast and PTSD. His skilled flow and vulnerability exploring violence have made him one of the leading voices of modern drill music.

28. Joey Purp

Joey Purp rappers

Joey Purp is a Chicago MC who has done much to reshape the city’s hip hop identity in recent years. As part of the Savemoney collective with Chance the Rapper, Vic Mensa, and others, Joey Purp’s music merges hip hop with soul, electronic, and more. He released acclaimed mixtapes like The Purple Tape before dropping his debut album QUARTERTHING in 2018. Joey Purp’s distinctive style showcases his technical rapping ability and vision beyond typical “drill” music. Tracks like “Morning Sex” display his versatility. Joey Purp continues to represent a progressive, genre-bending vision of what Chicago hip hop can be.

27. Juice WRLD

Juice WRLD Rappers

Juice WRLD took the music industry by storm before his untimely death in 2019. Born Jarad Higgins in 1998, he rose to fame on SoundCloud with his breakout hit “Lucid Dreams.” The track catapulted him to a major label deal. Juice WRLD’s emo-influenced lyrics and melodic style made him one of rap’s biggest streaming artists. His album Goodbye & Good Riddance reached #6 on the Billboard 200. Unfortunately, Juice WRLD died from an accidental overdose at just 21 years old, ending his skyrocketing career. In the span of just two years, the Chicago native made an indelible mark on hip hop and left behind a considerable catalog of hits.

26. Kanye West

Kanye West rappers

Kanye West is arguably the most famous and influential rapper to come out of the city of Chicago. Born on the South Side in 1977, Kanye first made waves as a producer, making beats for Jay-Z, Talib Kweli, and Alicia Keys. He then emerged as a rapper with his 2004 debut The College Dropout, acclaimed for its soulful production and conscious lyrics. His following albums, like Late Registration, Graduation, and My Beautiful Dark Twisted Fantasy all changed hip hop and pop music. A genius producer and iconic rapper, Kanye has become one of the best-selling artists of all time. Though controversial for his antics, Chicago native Kanye West has undoubtedly left a legacy as one of the greatest hip hop artists ever.

25. KB Mike

KB Mike rappers

KB Mike is an up and coming rapper from Chicago keeping the traditional foundations of hip hop alive. He started gaining attention in Chicago’s underground in the mid 2010s with mixtapes like Black Soap. KB Mike stands out for his jazzy, soulful production and thoughtful lyrics touching on spirituality and self-improvement. His nimble flow allows him to ride any style of beats. KB Mike has described his music as “lyrical, raw, authentic hip hop.” Remaining independent, he represents the hungry underground rap scene that still thrives in Chicago. KB Mike has collaborated with other local acts like Sidewalk Chalk and continues to build his fanbase the old fashioned way through nonstop shows and mixtapes.

24. King Louie


King Louie is a rapper who was seminal in helping develop Chicago’s drill sound. Born Louis Johnson in 1987, he first emerged in the underground scene with mixtapes like Boss Shit in 2011. King Louie’s early tracks like “Val Venus” incorporated the sinister style that would come to define drill. He also popularized Chicago’s slang term “sipping drank.” As drill blew up, King Louie collaborated with artists like Kanye West and signed to Epic Records. However, label issues followed. King Louie continues to release music as an independent artist. His influence looms large over Chicago trap, paving the way for artists like Chief Keef.

23. King Von

King Von Rappers

King Von was one of the most popular new rappers emerging from the Chicago drill scene before his death in 2020. Born Dayvon Daquan Bennett in 1994, he is best known for his hit 2018 single “Crazy Story.” King Von’s gritty storytelling about violence growing up resonated with fans. He collaborated with high profile artists like Lil Durk and Polo G, and seemed on the verge of mainstream stardom. Tragically, King Von was shot and killed outside a club in Atlanta at just 26 years old. Despite only releasing one album, King Von’s rise to fame was meteoric, and echoes of his signature style can still be heard in Chicago drill.

22. Lady XO

Lady XO rappers

Chicago rapper Lady XO brings a unique perspective to hip hop, rapping and singing about relationships as a married woman. She originally started by sharing relationship advice and funny videos as part of the married duo XO Whoa and Zillionaire. The popularity of her catchy 2013 track “Actin’ Up” convinced Lady XO to pursue music further. She has released mixtapes and EPs mixing R&B style melodies and choruses with her charismatic rapping. Lady XO also works to empower women, partnering with organizations like Ladies of Virtue and The Dreamcatcher Foundation. With her mature point of view and catchy music, Lady XO is poised for more success.

21. Lil Durk

Lil Durk rappers

Lil Durk is one of the most successful rap stars to come out of Chicago’s drill movement. Born Durk Derrick Banks in 1992, he first gained notoriety with his 2012 mixtapes I’m A Hitta and Life Ain’t No Joke. Early tracks like “L’s Anthem” displayed his authentic lyrics about Chicago gang life. Lil Durk founded the rap collective Only The Family (OTF) along with longtime collaborator Lil Reese. His 2013 mixtape Signed To The Streets brought more buzz. In recent years, he’s found crossover success with albums like The Voice and Just Cause Y’all Waited 2. Lil Durk’s distinctive voice and real lyrical ability have made him one of the faces of the drill scene.

20. Lil Eazzyy

Lil Eazzyy rappers

Lil Eazzyy is an up and coming rapper associated with Chicago’s OTF crew alongside artists like Lil Durk. He started taking music seriously around 2018 and began attracting attention in Chicago’s underground scene. Lil Eazzyy is known for his high energy delivery and catchy hooks. After releasing mixtapes and singles like “Rockstar,” he signed with Motown Records in 2021. Lil Eazzyy has described his musical style as cinematic and wants to be a rap superstar. With co-signs from established artists, he appears poised to break out from Chicago’s crowded rap scene soon. At just 21 years old, his career is just getting started.

19. lil moe 6blocka

il moe 6blocka rappers

lil moe 6blocka is a fast rising young rapper associated with Chicago’s prominent Gangster Disciples street gang. Still a teenager, he started developing a name in 2019 releasing tracks like “Hood Cry” and “Blicka Blicka.” lil moe 6blocka quickly built a strong YouTube following with his intense drill style and videos depicting the harsh realities of life in Chicago. He is best known for his hit 2020 single “Death of 150” which accused rival gang members of killings. lil moe 6blocka has collaborated with fellow GD rappers like Prince Dre. With his aggressive delivery and street credibility, he has established himself as one of the more popular new faces in Chicago’s drill scene.

18. Lil Reese

Lil Reese rappers

Chicago native Lil Reese was an early pioneer of the drill sound along with rappers like Chief Keef. Born Tavares Taylor in 1993, he met Chief Keef in high school before the two linked up creatively. Lil Reese first gained fame with his 2012 mixtape Don’t Like. His early tracks like “Us” and “Beef” exemplified drill’s grim street lyricism. Lil Reese joined Chief Keef’s Glory Boyz Entertainment crew and collaborated on popular tracks. However, legal issues have stalled Lil Reese’s progress. He survived being shot in the neck in 2019. Despite setbacks, Lil Reese’s snarl and raw aggression established him as one of drill music’s architects.

17. Lil Zay Osama

Lil Zay Osama rappers

Lil Zay Osama is a prominent Chicago drill rapper known for his rapid fire flow. He started rapping as a teen in 2015, gaining notoriety with tracks like “T’d Up.” Lil Zay Osama built a strong catalog of underground mixtapes before signing with Columbia Records in 2020. He reached a wider audience with hits like “Changed Up” and “Them O Block Boys” featuring G Herbo and Lil Durk. Unafraid to rap candidly about violence, his lyrics provide an unfiltered look at Chicago street life. Still in his early 20s, Lil Zay Osama continues to rep Chicago drill music at its most authentic.

16. Lucki

Lucki rappers

Alternative hip hop rapper Lucki originated in Chicago’s indie scene before finding wider success. Born Lucki Eck$ in 1996, he first grabbed attention with mixtapes like Alternative Trap in 2012 defined by his drowsy, xanax-fueled sound. Lucki’s early music explored darker subject matter like addiction and depression. Signed to indie label Fool’s Gold, he continued refining his moody, hazy style on projects like Freewave 3. Lucki started reaching more mainstream listeners with his 2020 album Flawless Like Me. Remaining creatively independent, Lucki’s aesthetic has made him one of the more unique voices to emerge from Chicago hip hop.

15. Lupe Fiasco

Lupe Fiasco rappers

Lupe Fiasco is one of the most prominent conscious rappers to come from Chicago. Born Wasalu Muhammad Jaco in 1982, he first made waves with his 2006 album Lupe Fiasco’s Food & Liquor which earned him three Grammy nominations. His sharp lyrics explored topics like skateboarding, poverty, and religion. Lupe Fiasco had even more success with his ambitious follow up albums The Cool and Tetsuo & Youth. Despite conflicts with Atlantic records, he’s remained an independent voice in hip hop. Lupe Fiasco’s mastery of storytelling and lyricism have made him one of Chicago’s most respected MCs.

14. Mick Jenkins

Mick Jenkins rappers

Mick Jenkins is one of the most prominent young rappers representing Chicago’s progressive hip hop scene. Born Jayson Jenkins in 1991, he first gained buzz with mixtapes like 2012’s The Mickstape. Mick Jenkins’ poetic lyrics fuse social commentary, spiritualism, and self-reflection. He broke through with his critically acclaimed 2015 album Wave[s] highlighted by songs like “Alchemy.” Remaining independent, Mick Jenkins has continued honing his jazz-influenced style. He often spreads positivity and empowerment rather than negative drill content. Along with artists like Noname and Saba, Mick Jenkins exemplifies the bright future of intellectual Chicago hip hop.

13. Montana of 300

Montana of 300 rappers

Montana of 300 is an underground rap phenom out of Chicago acclaimed for his aggressive punchline-driven style. Born Walter Bradford in 1986, he originally founded the Battle Rap group Battle League before going solo in 2012. Montana of 300 first drew attention with his breakout hit “Chiraq Remix” displaying his ferocious battle flow over drill production. Despite remaining independent, he has released numerous mixtapes and EPs since 2013 cultivating a devoted fanbase. Songs like “Holy Ghost” showcase Montana’s verbal dexterity and technique. His skilled freestyling also earned him attention. Montana of 300’s relentless tracks have made him one of the Windy City’s most respected lyricists.

12. Noname

Noname rappers

Noname is a positive, jazz-influenced rapper who came up in Chicago’s vibrant poetry scene. Born Fatimah Nyeema Warner in 1991, she first gained attention working with artists like Chance the Rapper. Noname’s2016 mixtape Telefone introduced her mellow style and displayed her technical lyrical ability. Her acclaimed 2018 debut album Room 25 expanded her sound, mixing neo soul and spoken word influences. Rarely giving interviews, Noname prefers letting her music speak for itself. Her unique perspective and content exploring identity have made Noname one of the most intriguing rappers to emerge from Chicago in the 2010s.

11. PGF Nuk

PGF Nuk rappers

PGF Nuk is an up and coming Chicago rapper making a name for himself in the city’s drill scene. Real name Octavious Williams, he started pursuing music seriously around 2018. PGF Nuk first drew attention with his appearance on Polo G’s hit song “Pop Out.” His own track “Relax” also gained buzz online that year. Since then, he’s released a steady stream of tracks like “Waddup Doe” and “Not From 63rd” to grow his profile. PGF Nuk is known for his deep voice and straightforward raw lyrics. Frequently collaborating with artists like G Herbo and King Von, he seems primed to blow up soon if he can continue developing his style and songwriting.

10. Polo G

Polo G rappers

Polo G skyrocketed to become one of the most popular new rappers to emerge from Chicago’s rap scene in recent years. Born Taurus Tremani Bartlett in 1999, he blew up on SoundCloud with his 2018 single “Finer Things.” He continued growing his buzz with songs like “Pop Out” featuring fellow Chicagoan PGF Nuk. In 2019, Polo G’s debut album Die A Legend made him a Billboard chart topper. His brooding lyrics about violence and fame connect with a wide audience. Polo G cemented his next big thing status with his 2020 album The Goat. Hailed for his authentic writing, Polo G is poised to carry Chicago rap music forward on the national stage.

09. Rhymefest

Rhymefest rappers

Rhymefest is a Chicago hip hop veteran who has made major contributions as both a rapper and activist. Born Che Smith in 1977, he co-wrote songs with Kanye West before releasing his acclaimed debut album Blue Collar in 2006. His pointed lyrics explore issues like poverty in the black community. Rhymefest famously called out violence in Chicago with the provocative track “Bang Bang.” In recent years, he’s focused more on social activism and politics in Chicago. After a public spat, Rhymefest and Kim Kardashian West worked together on criminal justice reform. As an MC, Rhymefest is revered for his thoughtful writing and calls for empowerment.

08. Rockie Fresh

Rockie Fresh rappers

Rising rapper Rockie Fresh found success blending pop, electronic music, and hip hop’s roots. Born Donald Pullen in 1991, he got started in music as part of the Chicago crew FTP. After mixtapes like Electric Highway and The Otherside, Rockie signed with Rick Ross and Maybach Music Group. His 2013 mixtape Driving 88 incorporated electronic elements and spawned the hit “What Ya Used To.” Rockie Fresh’s 2016 album The Night I Went To… saw him continue experimenting with lively beats and catchy hooks. Hailing from Chicago’s diverse rap scene, Rockie’s outside the box style has helped him build a growing fanbase.

07. Rooga

Rooga female rappers

Rooga is one of the rising stars representing Chicago’s drill rap movement. Born Jevon Smart in 1997, he first grabbed attention with his breakout 2018 single “Hang Wit Me.” The popular track displayed his gruff yet melodic vocal style and led Rooga to sign with Empire Distribution. He further grew his profile appearing on songs with artists like G Herbo. In 2021, Rooga released the acclaimed mixtapes Dalia and Dolo displaying his talent for addictive hooks and streetwise lyricism. Hailing from Chicago’s intimidating O-Block, Rooga’s real life experiences fuel his potent drill music.

06. Saba

Saba rappers

Saba is an alternative Chicago hip hop artist praised for his poetic lyrics and experimental musicality. Born Tahj Malik Chandler in 1994, he comes from the city’s influential Pivot Gang collective. Saba first gained buzz with mixtapes like 2012’s GETCOMFORTable. His 2016 breakthrough album Bucket List Project showcased his jazz-rap style to acclaim. Saba continued refining his sound on 2018’s Care For Me, an introspective concept album dealing with loss. His vulnerable songwriting combined with unusual beats have made Saba a critical darling. Though often overlooked commercially, he remains a progressive force within Chicago’s hip hop landscape.

05. Saba Pivot

Saba Pivot rappers

The alternative hip hop group Pivot Gang is led by rapper Saba and includes rappers Joseph Chilliams, MFnMelo, and producers daedaePIVOT and daoud. Originating from Chicago’s West Side in 2011, Pivot Gang first drew attention with mixtapes like 2014’s Jimmy which spotlighted members’ jazzy beats and dense lyricism. They’ve continued developing their chemistry across projects like You Can’t Sit with Us. Pivot Gang is known for their DIY approach, real life subject matter, and knack for infectious hooks. Together they represent a grassroots Chicago rap collective unafraid to experiment and push boundaries creatively. Though still underground, they’ve built a devoted base within alternative hip hop.

04. Shawnna

Shawnna rappers female

Shawnna became one of Chicago’s first female rap stars in the early 2000s. Born Rashawnna Guy in 1974, she got started battle rapping and appearing on tracks by local artists. After guesting on Ludacris’s hit “What’s Your Fantasy,” she signed to Def Jam South in 2002. Shawnna’s debut album Worth tha Weight went platinum behind horny club anthems like “Gettin Some.” She also collaborated with high profile artists like T.I., Lil Kim, and Remy Ma. Though her sales declined after her debut, Shawnna’s sex positive lyrics broke ground for female rappers. She continues releasing music independently today.

03. Shoebox Baby

Shoebox Baby Rappers

Shoebox Baby is an up and coming teenage rapper making waves in Chicago’s drill scene. Still in high school, he’s gained a strong local buzz with tracks like “Kobe” and “Money.” Shoebox Baby’s youthful voice belies his mature lyrics documenting street life. He often collaborates with fellow Chicago drill rappers like King Von and Polo G. Shoebox Baby also attracted attention through his ongoing beef with fellow rapper FBG Duck. Though controversial for his graphic content, Shoebox Baby’s precocious talent and growing fanbase suggest a promising future for the young Chicagoan.

02. Twista

Twista rappers

Twista is a legendary Chicago MC revered as one of the fastest rappers of all time. Born Carl Terrell Mitchell in 1973, he rose to fame in the ’90s collaborating with Do or Die and releasing his solo album Adrenaline Rush in 1997. Twista became hugely influential in hip hop for tracks like “Is That Your Chick” displaying his supersonic, tongue twisting flow. Though later albums like Kamikaze were popular, Twista struggled to regain his 90s buzz. He remains a local hero in Chicago. Today Twista continues to display his chops through guest verses and performances. Over 25 years into his career, his speed and rhyme skills are entirely unmatched.

01. Vic Mensa

Vic Mensa

Vic Mensa emerged as part of Chicago’s diverse hip hop renaissance of the 2010s. Born Victor Kwesi Mensah in 1993, he first gained traction with the alternative rap group Kids These Days before going solo. Vic Mensa got noticed nationwide with his 2013 mixtape Innanetape. His following EPs and debut album The Autobiography saw him blend rock, electronica, and hip hop. Vic is known for his introspective, socio-political lyrics about topics like racism and addiction. He’s collaborated with stars ranging from Chance the Rapper to Skrillex. Vic continues to make an impact both through music and activism in Chicago.

FAQs for Chicago Rappers:

1. Who are some of the most influential Chicago rappers of all time?

Some of the most influential Chicago rappers of all time include Kanye West, Common, Twista, Lupe Fiasco, Chief Keef, and Chance the Rapper. These artists have pioneered new hip hop styles, taken Chicago rap worldwide, and influenced countless other MCs.

2. What rap styles did Chicago help create?

Chicago rappers were instrumental in creating and popularizing rap styles like drill, trap, “bounce” rap, and alternative hip hop. Drill music is the city’s most well known style, defined by dark, gritty lyrics over hard hitting beats.

3. Which Chicago rappers started drill music?

Chief Keef is considered the pioneer of the drill sound, along with fellow rappers like Fredo Santana, Lil Durk, Lil Reese, and King Louie. These artists created drill’s slow, ominous production and realist violent lyrics drawing from Chicago street life.

4. Who are some of Chicago’s most popular rappers today?

Some of the current most popular and influential Chicago rappers right now are Chance the Rapper, G Herbo, Polo G, Juice WRLD, Lil Durk, Vic Mensa, Noname, Saba, Mick Jenkins, King Von, and Da Brat. The city continues to produce diverse, talented MCs.

5. What themes are common in Chicago hip hop?

Chicago rappers often focus on themes of street life, gang disputes, gun violence, and overcoming hardship in the city’s rougher neighborhoods. Drill artists portray gritty realities, while conscious rappers promote empowerment. Other common topics include partying, relationships, braggadocio, and more universal subjects.


Chicago’s impact on hip hop cannot be overstated. From pioneers like Common and Twista to drill innovators like Chief Keef, the city’s MCs have shaped rap music’s evolution. The breadth of talent originating from the Windy City is staggering. Underground lyricists, mainstream pop stars, gritty street rappers – Chicago has produced them all. The city’s diversity gets reflected across every era and style of hip hop. Even amidst tragedy, new voices emerge to carry on Chicago’s hip hop legacy. Legends like Kanye West and Lupe Fiasco laid the foundation. Today, young stars like Polo G, Chance the Rapper, and Vic Mensa continue the heritage. It seems certain that Chicago will keep birthing the next generation of talented, original rappers for years to come. The city remains a vital epicenter shaping hip hop culture.

Chicago rap started with modest beginnings. Over decades, it has grown into a dominant force in the genre. The city’s distinctive styles and massive rosters of talent are a testament to its importance. Chicago rappers were crucial in pioneering genres like drill that changed hip hop’s sound. The city’s diverse MCs have found global success repping their hometown. Tragedy has struck down too many Chicago artists in their prime. Yet new voices always arise to lead the scene forward. From underground innovators to multi-platinum superstars, Chicago’s rappers have left an indelible mark on hip hop. The city will continue minting new talent and influencing broader culture. Chicago’s role in birthing and progressing rap music should never be forgotten.

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