The future of music

35 Best Chicago Rappers of All Time

June 19, 2023
chicago rappers

Chicago has something for everyone, whether you’re looking for fine dining, famous architecture, exciting sporting events, or, most importantly, great music. 

Known as ‘The Windy City,’ Chicago is unique and special for many reasons, including its rich history and vibrant culture. 

Rap, in particular, has made an important contribution to the world’s musical landscape. 

When compared to cities such as New York, Atlanta, and Compton, the importance of Chicago in the rap scene is almost always understated.

Nonetheless, Chicago has produced some of the best rappers of all time.

Rappers from Chicago have been among the most influential hip-hop artists over the last two decades. 

Chicago has produced a plethora of talented MCs: from Ye (formerly known as Kanye West) in the mid-2000s to the Chief Keef movement in the 2010s to Polo G right now.

From the drill rap movement, which influenced an entire generation of rappers today, to the independent scene spearheaded by Chance the Rapper, to veteran MCs like Twista, Do or Die, Crucial Conflict, and global superstars like Ye, Common, Lupe Fiasco, and Lil Durk, Chicago hip-hop is diverse and rich.

If you enjoy discovering new rap artists to follow, keep an eye out for Chicago rappers because there is always something fresh and interesting to hear in this city.

Here are the thirty-five best Chicago rappers of all time, there are some well-known artists on this list, but there may be some new names to add to your playlist as well.

1. Chief Keef

It was Keef’s “I Don’t Like,” a raw, hypnotic track featuring Lil Reese, that catapulted him to the top of the rap game in 2012. 

When Ye produced a GOOD Music version of the song, labeling it “Don’t Like,” the Chicago drill wave began.

While Keef’s rap career may not have gone as planned when he first arrived on the scene, things have turned out better for the rapper in some ways.

Many rappers today have been directly influenced by Keef’s DIY approach as well as his melodic emphasis on rapping.

2. Lil Durk

Lil Durk has remained one of the most recognizable Chicago rappers in the game, from his early days as a drill rapper known for his mixtape-slinging to his more reflective records in recent years. 

One of the top rappers right now, Durk has helped to define an entire subgenre with his combination of melodic delivery and drill raps.

Early on, Lil Durk’s verbose and loquacious style distinguished him from his peers. 

His lyrics changed throughout his career, focusing more on the unintended negative effects of gang life in real life than on its glamorization. 

Durk has scored a hit single with Drake (“Laugh Now Cry Later”) and two number-one albums with Lil Baby, 7220, and The Voice of the Heroes.

3. Juice WRLD

Before dying of a drug overdose at the age of 21, the Chicago rapper’s emotionally vulnerable style catapulted him from SoundCloud to massive stardom almost overnight. 

Juice had found huge success with a tender-voiced combination of melodic hip-hop, emo, and pop-punk in the three years since he started releasing music on SoundCloud.

Nine months before his death, Death Race for Love, his second album reached number one on Billboard’s chart. 

His music was notable for its honesty and emotional vulnerability.

In the intro to “Lean Wit Me,” from his platinum-selling debut Goodbye & Good Riddance, he sings, “Drugs got me sweatin’, but the room gettin’ colder / Lookin’ at the devil and the angel on my shoulder / Will I die tonight? I don’t know, is it over? / Lookin’ for my next high, I’m lookin’ for closure.”

His lyrics give a sense of eery foreshadowing if you will.

4. Ye (Kanye West)

Although he may be a controversial artist, West’s body of work cannot be underestimated; it is a string of ground-breaking, genre-defining tracks that has few if any, worthy comparisons, especially not in this millennium.

West’s musical career has been marked by frequent stylistic shifts and a variety of musical approaches. 

Since making his debut, West has experimented more with his music and lyrics to create progressive hip-hop music while still keeping a relatable pop sensibility.

“All Falls Down” (2004), “Flashing Lights” (2007), “Niggas in Paris” (2011), “Blood on the Leaves” (2013), “Fade” (2016), or “Off The Grid” (2021) are some of the songs that display how talented Ye truly is.

5. Calboy

Calboy creates music that is influenced by a wide range of artists, including Chance the Rapper, Michael Jackson, and The All American Rejects. 

He made a local breakthrough with his releases “ANXIETY” and “Calboy the Wild Boy” in 2017. 

Calboy is one of rap’s most exciting new faces, emerging from Chicago’s South Side with equal parts melody and tenacity. 

His breakthrough hit, “Envy Me,” is buoyantly soulful and crammed with hooks, but it’s also infused with the violence of Calboy’s hometown.

6. Joey Purp

Joey Purp, while a new name on a global scale, is no stranger to his hometown of Chicago. 

The resilient lyricist rose to prominence as part of the SaveMoney collective’s rap duo Leather Corduroys.

His cited musical influences include the Wu-Tang Clan, Sex Pistols, and The Velvet Underground, among others. 

As a result, he has developed a distinct sound that adds something special to his mixtapes and debut album, Quarterthing.

His 2016 project iiiDrops is what catapulted him into the spotlight.

iiiDrops was hailed as one of the year’s best hip-hop endeavors by critics and fans alike, with singles “Cornerstore,” “Photobooth,” and “Girls @” providing momentum for an eagerly anticipated release.

7. Montana of 300

Chicago MC Montana of 300 spent 2015 adding his vocals to some bootleg remixes and ended the same year working with Ye.

Fire in the Church, his debut studio album, was released in 2016.

He is best known for his rap style, which incorporates trap music, R&B, and drill beats, as well as remixes of hit songs that, like his originals, frequently include religious subtext.

8. Rockie Fresh

Rockie Fresh is renowned for his alternatively influenced hip-hop style and collaborations with recording artists such as Fall Out Boy’s Patrick Stump and Good Charlotte’s Joel & Benji Madden.

Rockie prefers a low-key mic approach that runs seemingly in contradiction with his rhymes’ precision and force. 

He released his first mixtape at the end of the 2000s before releasing a proper album Destination in 2019.

9. Lil Zay Osama

Lil Zay’s success story is due to his infectious music, lyrics, and melodies that have channeled the spirit of the culture. 

Once Zay started making videos and posting them to YouTube, he quickly realized that music was his calling.

His music, which he describes as ‘pain music,’ reflects his violent upbringing on Chicago’s South Side and explores topics such as grief, trauma, and survival.

10. Fredo Santana

Coleman, like many of his drill music contemporaries, rarely raised his voice, instead delivering self-assured and grim depictions of violent street life over slow beats that boomed and rattled.

Fredo Santana, rapper Chief Keef’s cousin, died of a seizure in 2018, which ended a promising life and career in music.

He produced several incredible songs during his active years, and his fans still think highly of him.

Trappin Ain’t Dead, his debut studio album, was released in 2013 by Savage Squad and peaked at number 45 on the US Top R&B/Hip-Hop Albums chart.

11. Open Mike Eagle

Open Mike Eagle is a well-known Chicago-raised, Los Angeles-based entertainer, comedian, and podcaster. 

He coined the term ‘art rap’ to describe his razor-sharp, literate hip-hop style. 

He continued to use his music as an outlet to process personal issues with 2020’s Anime, Trauma, and Divorce.

Component System with the Auto Reverse, a much rawer, mixtape-style release, was also released in 2022.

12. Lupe Fiasco

Fiasco has been credited as a pioneer of the conscious hip-hop movement, which focuses on social issues, alongside other rappers such as Common, Mos Def, and Talib Kweli. 

Fiasco, who received four Grammy nominations for Food & Liquor, including one for best urban/alternative performance for “Daydreamin’,” laid the groundwork for his most powerful, multi-layered project to date. 

On the dark but pop-leaning single “Superstar,” released on his 2007 album The Cool, the Chicago MC unabashedly rapped about the perils of fame, gun violence on “Hip-Hop Saved My Life,” and health consciousness on “Gotta Eat.”

In his songwriting, Fiasco employs a variety of lyrical techniques including metaphors and lyrical statements. 

Because of his musical theater background, the rapper sees hip-hop as a medium conducive to storytelling, which is a major component of his lyrics.

13. G Herbo

At the age of 16, G Herbo released several mixtapes on the expanding Chicago drill scene that positioned him as the city’s future. 

A few years after the first wave, Lil Herb (as he was then known) and Lil Bibby emerged. 

While still rapping over the same nihilistic production, they displayed greater maturity and introspection than their precursors. 

G Herbo’s mixtape Welcome to Fazoland had a significant impact on the rap scene at the time. 

The rapper built his legend on true-life hood stories, using a deep and gravelly voice perfectly suited to demonic beats. 

G Herbo has steadily risen over the last decade, staying true to his roots, and rapping about the violence and trauma that living in his city brings.

14. Polo G

Many older rap fans complain that MCs under the age of 25 have talent and charisma, but their subject matter is shallow, with few stories of rags to riches. 

This criticism cannot be leveled at Polo G.

No artist in any medium has devoted as much time in the past few years to dissecting the lifelong trauma of growing up in a dangerous, underdeveloped socio-economic environment as Polo G has.

Since 2019, he has put out dozens of songs and verses, almost all of which detail his PTSD in a vulnerable yet stoic manner.

He frequently discusses poverty, violence, and trauma, but his words also inspire hope and resilience.

Polo G rose to prominence with his debut single “Finer Things” in 2018, and his debut album Die a Legend and his sophomore album The Goat have both been successful.

15. King Von

Von was best known as a chronicler of street life in Chicago, weaving tales of tense nights on the streets and his desire to escape the gangster’s mindset. 

Indebted to first-generation artists like G Herbo, Chief Keef, and King Louie, Von existed in the post-drill Chicago rap landscape while also attempting to infuse the genre with his own distinctive stylistic aesthetics. 

His rhymes are empathetic which softens the deadpan nihilism in his narrative songs.

Few rappers are able to create songs that are relatable to the stress, trauma, and pain of growing up in inner-city Chicago, a target of both police and neighborhood rulers.

In 2020, Von died of gunshot wounds a week after his new album, Welcome to O’Block, had been released. 

The album’s title emphasizes Von’s strong desire to return home, to make amends with those who had wronged him, and to infuse his community with a strong, inspiring presence, which makes his death even more devastating.

16. Twista

Although he set the world record for the fastest English rapper in 1992, saying 598 words in 55 seconds, according to Guinness World Records, he didn’t become an immediately successful rapper. 

But after releasing Kamikaze, which topped the Billboard 200 album chart in 2004, his luck began to change.

Twista rapped sharper, used metaphors, and applied all of his MC skills to a new style that was gaining traction in Chicago’s ghettos.

The lyrics of the lead single on Kamikaze, “Slow Jamz,” include elements of hip-hop, pop rap, R&B, and soul. 

17. Noname

Noname has paved a lane for herself with the perceptive and unflappable lyrics that shade the full-length albums, Telefone (2016) and Room 25 (2018).

Noname’s sound is characterized by clever, visual social commentary presented over jazz-infused moods and nods to old-school hip-hop beats. 

Her music has a progressive soul vibe to it, with hip-hop poetry mixed in with a genre-fluid, natural rhythm.

Noname is a poet, performer, and producer, who also runs a book club dedicated to radical texts by authors of color. 

18. Queen Key

With the single “My Way” which became a huge streaming success, Queen Key is also known as the Queen of Girl Power and Hip-Hop Humor. 

Her hip-hop style is described as girl power and uncontrollable laughter, though some people may consider her to be a little less-than-ladylike. 

But it’s what makes her one of the most well-liked young stars in the rap industry. 

With her hysterically funny and sexually explicit rhymes, Queen Key hopes to empower women and subvert hip-hop gender stereotypes.

19. Da Brat

Da Brat established herself as a tough, profane rhymer with an unwavering attitude and lyrical abilities. 

Because LGBTQ+ fans don’t have a lot of representation in the rap industry, her status as a queer icon is significant to her fans.

By working with some of the biggest names and releasing hit songs, she is still a vital player in the rap industry today. 

Her debut album, Funkdafied, was certified Platinum in 1994, making her the first female solo rap artist to do so.

20. Mick Jenkins

Creating an unconventional, rich, genre-fluid sound with jazz, soul, and funk influences, Jenkins has made a name for himself over the last decade through the power of his music. 

The rapper deviated from the mainstream path when he made his debut around the same time as the Chicago drill movement was at its peak.

His voice is evocative, commanding a sense of authority, or at the very least self-assurance, that allows him to use his own and others’ experiences in search of higher truths. 

However, some topics will always be difficult to discuss, and his latest album Elephant in the Room (2021) is about confronting those issues.

21. Chance The Rapper

From his incredible lyrical abilities to his ever-popular collaborations, it’s no surprise that Ye, Childish Gambino, and Twista have all leaped at the idea of working with the Chicago-born rapper and record producer.

Described as dynamic and upbeat, Chance’s music is characterized by jazz-inspired melodies and gospel influences. 

While incorporating choir in his songs, Chance’s lyrics often refer to Christian theology, his struggles with religion, and his upbringing. 

Chance’s third mixtape, Coloring Book, was the first streaming-only album to win a Grammy for Best Rap Album in 2017.

He has achieved mainstream success and popularity for his unique sound since his debut.

22. Common

Common rose from underground hip-hop to become one of the genre’s absolute greatest. 

Since his debut, Can I Borrow A Dollar?, in 1992, the South Side rapper curated an enormous discography of exploratory, inspiring soundtracks and a multitude of head-nodding, thought-provoking singles.

One of his best songs to date is “I Used To Love HER,” in which he embodies hip-hop to create a song about the music he once adored.

23. Taylor Bennett

Taylor Bennett, a Chicago native, worked hard to emerge from the shadow of his older brother, Chance the Rapper.

Taylor Bennett became a queer icon for contemporary rap after coming out as bisexual.

His artistry, however, goes beyond his sexual orientation or his relationship with Chance the Rapper; his music is renowned for incorporating a wide range of musical genres.

24. Earl Sweatshirt

Earl Sweatshirt is known for his deep baritone and creatively languid style, which has lyrically shifted from deeply subjective alt-rap to macabre horrorcore.

Dubbed a Hip-Hop Prodigy for his experimental hip-hop styles, Earl Sweatshirt has a Grammy nomination for his debut album, Doris, as well as an MTVU Breaking Woodie Award.

Although Earl Sweatshirt has a reputation for rapping about sinister and divisive subjects, the themes in his songs have become more subdued as he has aged.

“Couch” (2010) and “2010” (2022) are contrasting songs in nature.

25. Lil Reese

He became popular in the early 2010s as a member of Chicago’s drill scene, where he collaborated with fellow rappers Chief Keef, Fredo Santana, and Lil Durk.

Reese was featured on Chief Keef’s single “I Don’t Like,” which peaked at 73 on the Billboard Hot 100, 20 on the Hot R&B/Hip-Hop Songs chart, and 15 on the Hot Rap Songs chart in 2012.

His fame grew following the release of his singles “Beef” and “Us,” the latter of which he remixed with Drake and Rick Ross for Ross’ mixtape The Black Bar Mitzvah

In 2019, Reese suffered critical injuries when he was shot in the neck, but the day after he was discharged, he released “Come Outside” as a message to his assailant.

26. Qwazaar

Qwazaar, a well-known underground hip-hop performer, co-founded the rap group Typical Cats and is a part of Outerlimitz. 

With a solid reputation as one of the city’s most diverse MCs, he’s well-known for his soulful approach, diverse subject matter, and energizing live performances. 

He has over a decade of notable solo and collaborative releases to his credit, most recently as one-half of the Stoned Giant duo with acclaimed beatmaker and multi-instrumentalist Batsauce.

27. Saba

Saba, a successful Black independent artist, has built his career on authenticity and musicality, making him one of this generation’s most significant and unique voices.

Saba collaborated with Mick Jenkins in 2012, when he released his first mixtape GETCOMFORTable.

His 2018 album CARE FOR ME earned him the Tribune’s Chicagoan of the Year honors.

The album is a heartbreaking release that finds Saba dealing with the fallout from his cousin John Walt’s murder in 2017.

28. Soulja Boy

Soulja Boy is a live entertainer and producer with a knack for writing catchy hooks. 

In September 2007, his single “Crank That (Soulja Boy)” debuted at number one on the Billboard Hot 100. 

His 2007 debut mixtape, Unsigned & Still Major: Da Album Before da Album, was followed by his debut album that same year. 

His single “Kiss Me thru the Phone” remains a popular pop-rap song to this day.

29. Dreezy

Dreezy is a rapper, singer, and actress who successfully juggles swaggering, confident lyricism with slick R&B hooks and energetic pop-trap production. 

After years of releasing mixtapes and EPs, she made her Interscope debut with No Hard Feelings in 2016. 

The album contained the platinum-certified hit “Body” and the gold-certified “Close to You.” 

Later, she went solo and released Hitgirl, a 2022 collaboration with Hit-Boy.

30. Famous Dex

Famous Dex, a Chicago rapper, began posting and uploading his hooky, Southern-influenced hip-hop in 2015.

“Pick It Up,” an A$AP Rocky collaboration, charted at number 54 on the Billboard Hot 100 that same year.

His 2018 debut album Dex Meets Dexter reached No. 12 on the Billboard 200 chart—an incredible accomplishment for a debut artist.

Although he has faced legal issues due to substance abuse, he has sought assistance so that he can continue to dazzle his audience with his promising talent.

31. Vic Mensa

Vic Mensa is an American rapper and singer, who has been vocal about the issue of gun violence. 

He has released one studio album, one collaboration album, one mixtape, five extended plays, and 38 singles (including 18 singles as a featured artist).

32. King Louie

King Louie has been credited with being one of the Chicago rappers who helped make the city’s hip-hop scene the “hottest” in 2012. 

His YouTube promotion methods helped him become one of the city’s newer rappers to gain national attention. 

His continuous release of music videos has allowed him to quickly gain a large following.

33. Rooga

Despite only having three albums to his name, the 29-year-old South Side rapper has been nominated for a Grammy Award for Album of the Year.

His preferred music genres are reggae and hip-hop/rap, and his most successful song “GD Anthem” has 11 million views on YouTube.

34. Psalm One

Psalm One has been a member of the groups Nacrobats, Rapperchicks, and Big Silky.

Active since at least 2002 with her latest album in 2020, Psalm One has released twelve albums, three mixtapes, seven EPs, and more than five singles.

35. Lil Bibby

Lil Bibby began his career in 2011 during the drill rap scene and released his debut mixtape, Free Crack, in 2013. 

Following his signing with Kemosabe Records, he released Free Crack 2 (2014) and Free Crack 3 (2015).

Best Chicago Rappers – Final Thoughts

Chicago is known for producing some of America’s best rappers. 

Rappers from Chicago typically rap about their city, hustling, and politics in general. 

The majority of Chicago’s young rappers are inspired by their successful and older counterparts. 

Chicago rappers draw inspiration from all over the country. 

While there is no distinct Chicago sound, each artist has a distinct voice and a seemingly unlimited pool of skills to draw from. 

Because of the fundamental issues they discuss in their music and the environment that allows rap musicians to thrive, Chicago rappers continue to be among the highest-rated in the country.

You may also like: Best Carolina Rappers

Will Fenton

Will, the founder of MIDDER, is a multifaceted individual with a deep passion for music and personal finance. As a self-proclaimed music and personal finance geek, he has a keen eye for futuristic technologies, especially those that empower creators and the public.

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