Chicago has long been a hotbed for hip hop talent, producing some of the most influential and popular rappers over the past few decades. While the city’s rap scene has gone through ups and downs, it has continued to churn out unique voices and styles that have impacted hip hop on a global scale. Here is a look at 19 of the top Chicago rappers of all time.
Here We Go with 19 Best Chicago Rappers
19. Kanye West
No discussion of Chicago hip hop would be complete without mentioning Kanye West. Since debuting in the early 2000s, West has become one of the most critically acclaimed and commercially successful rappers of all time. His album The College Dropout helped bring soul samples and conscious lyricism back into the mainstream, while later efforts like Graduation and 808s & Heartbreak expanded the sound of hip hop with electronic and pop influences. West also helped launch the careers of fellow Chicago rappers Common and Lupe Fiasco through his GOOD Music imprint. With 21 Grammys and over 140 million records sold, Kanye stands as Chicago’s most famous rap export.
As one half of the ’90s rap duo Common Sense, Lonnie Rashid Lynn Jr. established himself as an underground favorite thanks to his thoughtful lyrics and fluid flow. After going solo as Common in the late ’90s, he gained wider recognition with albums like Be and Like Water for Chocolate, earning praise for his poetic style and socially conscious themes. Common eventually went on to find success in Hollywood as well, showing up in movies like American Gangster and Selma. He remains one of the most respected lyricists to come out of Chicago.
17. Lupe Fiasco
Lupe Fiasco is often credited with helping to pioneer the more lyrical side of mid-2000s hip hop. After overcoming early struggles with Atlantic Records, he broke through with critically acclaimed albums like Food & Liquor and The Cool. Fiasco set himself apart with his sharp wordplay and storytelling, rapping about sociopolitical issues over eclectic production. Though he has kept an independent approach since leaving Atlantic, he remains an influential figure in conscious hip hop.
Known for his incredibly fast rapping style, Twista has been a staple of Chicago hip hop since the early ’90s. After flirting with mainstream success on albums like 1997’s Adrenaline Rush, he finally broke through with his 2004 album Kamikaze, which featured the megahit “Slow Jamz” with Kanye West and Jamie Foxx. In addition to his solo career, Twista has frequently collaborated with other Chicago artists like Do or Die and Crucial Conflict. Even as rap has moved away from his rapid-fire flow, Twista remains an impressive technician on the mic.
15. Chief Keef
Chief Keef rose to fame as part of Chicago’s drill scene, known for grim subject matter and hard-hitting production. His 2012 mixtape Finally Rich brought the drill sound to the rest of the world, driven by hits like “I Don’t Like” and “Love Sosa.” Keef’s success helped pave the way for fellow Chicago drill rappers like Lil Durk, Lil Reese, and Fredo Santana. Though legal issues have hampered his output, Keef remains one of the most influential young rappers to come out of Chicago for popularizing the drill sound.
14. Chance the Rapper
Making his name through various mixtapes, Chance the Rapper broke out with his 2013 project Acid Rap. His soulful, gospel-infused sound showed a lighter side of Chicago hip hop and highlighted his technical skills. As an independent artist, Chance became the first rapper to win a Grammy based solely on streaming mixtapes. He is also known for his activism and philanthropy in Chicago, frequently collaborating with fellow Chicago natives like Noname and Saba on social initiatives.
13. G Herbo
Originally known as Lil Herb, G Herbo has been a mainstay in Chicago’s drill scene since his early teens, working with rappers like Lil Durk andproducers like Lil Bibby. His gritty lyrics and no-nonsense delivery epitomize the hardness of drill music. Albums like Ballin Like I’m Kobe and PTSD have shown his growth beyond drill, with more confessional themes. Through his NLMB crew, G Herbo remains closely connected to Chicago’s hip hop roots.
Cupcakke (born Elizabeth Eden Harris) brings a highly explicit and theatrical style to Chicago’s rap scene. After grabbing attention with provocative songs online, she has released a string of mixtapes and albums since 2016, earning praise for her animated flow and wordplay. Tracks like “Vagina” and “Deepthroat” showcase her raunchy brand, which has been controversial but commercially successful. Cupcakke continues to be one of Chicago’s more unique rap voices.
11. Vic Mensa
A former member of the group Kids These Days, Vic Mensa has carved out a place among Chicago’s second wave of new school talent. After going solo in 2013, he garnered notice with projects like INNANETAPE before joining Roc Nation in 2015. Mensa’s style melds diverse influences like house music and punk rock with his conscious, socially aware lyrics. His intense performance style has helped him stand out from the pack. Though he hasn’t reached quite Kanye’s level of fame, Mensa remains a rising figure in Chicago hip hop.
10. Juice Wrld
Part of a post-“mumble rap” wave, Juice Wrld became a streaming giant with hits like “Lucid Dreams” and “All Girls Are the Same.” His melodic, emo-influenced style connected with millions of young fans. Though Juice first hit it big online in 2017, he was signed by Lil Bibby’s Grade A Productions set in Chicago. Tragically, Juice Wrld passed away from an accidental overdose in 2019 at just 21 years old, cutting short a promising career. He is remembered as one of the artists who helped introduce the lo-fi, melodic rap style to the mainstream.
09. Polo G
Polo G is one of the newer faces of Chicago rap, achieving success on the Billboard charts in the late 2010s and early 2020s. After a difficult upbringing around Chicago’s Cabrini-Green projects, he started uploading songs online and caught the attention of Columbia Records. Tracks like “Pop Out” with fellow Chicagoan Lil Tjay demonstrated his modern drill-influenced sound marked by heartfelt lyrics. Still in his early 20s, Polo G looks to have a long career ahead repping contemporary Chicago rap.
08. G Herbo
Initially part of Chief Keef’s Glory Boyz crew, Lil Reese carved out his own niche with his menacing vocal tone and delivery. Tracks like “Us” and “Beef” established him as one of the original rising stars of the Chicago drill scene. While legal issues sidelined him for a few years, Reese remained connected to Chicago hip hop through collaborations with rappers like Lil Durk. He represents the hardcore gangsta rap wing of Chicago’s drill sound.
Formerly known as Noname Gypsy, Noname brings a jazzy, soulful vibe to Chicago hip hop. After gaining attention for her appearance on Chance the Rapper’s “Lost,” she released her acclaimed 2016 mixtape Telefone. Her debut 2018 album Room 25 further showed her poetry-infused style and deft wordplay. Rarely explicit, Noname uses her music to celebrate human experiences and give voice to the oppressed. Her unique approach makes her one of the more distinctive artists in modern Chicago rap. Know more about NBA Youngboy.
A frequent collaborator with artists like Chance the Rapper and Noname, Saba adds a soulful, jazz-rap element to Chicago’s hip hop landscape. Since his 2015 breakthrough mixtape ComfortZone, he has released increasingly acclaimed projects like 2018’s CARE FOR ME, which delved into difficult personal experiences. Still early in his career, Saba continues to earn praise as one of the most promising rappers and producers currently repping Chicago.
05. Young Pappy
Though his career was cut short by tragedy, Young Pappy emerged as one of the pioneers of Chicago’s drill movement. Mixing aggression with lyricism, tracks like “Killa” built his buzz online in the early 2010s. He also collaborated with fellow Chicago rappers like Montana of 300. Sadly, Young Pappy was gunned down in a shooting in 2015 at just 19 years old. His music stands as a testament to his potential, had he been given more time to develop his talent.
04. Do or Die
Do or Die had Chicago rap fans going “Hypnotize” in the late 90s with their smash hit of the same name. The group of Belo Zero, Nard and AK-47 reached their peak with 1996’s Picture This, which took their hard-hitting street tales to the mainstream. While they never again reached the heights of “Hypnotize,” Do or Die remains an influential group representing Chicago’s early rap history. Members like Belo Zero also later nurtured the careers of newcomers like Chief Keef.
03. Bump J
Active since the 1990s, Bump J had a hand in pioneering the Chicago rap sound. His 2003 track “Move Around” helped set the template for what later became drill music. While legal troubles derailed his career for a few years, Bump J returned to reconnect with rising Chicago stars like Lil Durk whom he had influenced. Though not as famous as other Chicago acts nationally, Bump J’s influence can be felt in the way he shaped early trap and drill music in the city.
02. Crucial Conflict
In the mid-90s, Crucial Conflict brought a rowdy, uptempo style with songs like “Hay” and “Scummy.” The group’s 1996 album The Final Tic was a local hit in Chicago that combined gangsta rap with youthful energy. While they never broke through commercially on a national level, Crucial Conflict’s early success proved Chicago had rap talent waiting to be unleashed. Their fast paced “riding music” still stands as an influence on later sounds coming out of the city.
Emerging from Chicago’s South Side, Psychodrama hit the rap scene in 1991 with their track “Little Man.” With a slowed down boom bap style, their music resonated with hip hop fans looking for something beyond gangsta rap. The group only released one official album, 1992’s Psychodrama, but it stands as a snapshot of Chicago’s early ’90s rap landscape as the genre gained traction in the city. Though underappreciated nationally, Psychodrama were hometown heroes for putting Chicago hip hop on the map.
This list shines a light on some of the many talented rappers that have emerged from Chicago over the years. As the birthplace of genres like drill, the city has contributed some of the most influential sounds and styles. From early trailblazers to today’s rising stars, Chicago rappers have made a tremendous impact. The Windy City continues to be a hub for diverse, innovative hip hop. Artists like Mexican rappers and Atlanta Rappers continue to build upon the foundation laid by Chicago greats. The future looks bright for Chicago to keep producing the next generation of rap icons.
Who are some of the most famous Chicago rappers?
Some of the most famous Chicago rappers include Kanye West, Common, Lupe Fiasco, Chief Keef, Chance the Rapper, and Twista. These artists have had major impact locally and across the hip hop world.
What rap styles did Chicago help create?
Chicago artists were instrumental in the creation of rap subgenres like drill and trap music. Chicago also developed its own fast-paced “chopper” rap style.
Is drill music still popular in Chicago?
Though it peaked around 2012-2014, drill music still has a strong presence in Chicago. Chief Keef, Lil Durk, Lil Reese, and artists coming up today keep the drill sound alive. However, Chicago rap continues to evolve beyond just drill.
What other cities have rap scenes connected to Chicago?
Nearby cities like St. Louis have collaborated with Chicago artists. But Chicago’s influence extends nationwide, as many rappers borrow styles like drill that started in the city. The Chicago scene has impacted hip hop across the U.S.
Who are some of the most popular female rappers from Chicago?
Some popular female rappers from Chicago include Cupcakke, Noname, Sasha Go Hard, Katie Got Bandz, and Rapsody. Each brings their own unique style and perspective to the Chicago scene.