Since the birth of hip-hop, Chicago has remained a cultural mainstay in the rap scene. So join me as I take you through 15 of the best Chicago rappers, as we pay homage to both old school and new school rappers.
The Best Chicago Rappers (TLDR)
Chicago has remained a hotbed of hip-hop, producing a host of great rappers over the years. Kanye West is one of the undisputed leaders of the scene, and Chance the Rapper has been successful for years. Chief Keef also became a leader himself in the 2010s.
For old school hip-hop fans, Common and Twista are two rappers who helped put Chicago on the map back in the 90’s.
Rapper, actor, producer, artist—Common is something of a renaissance man and an industry staple. Working with Common is a sign one has “made it” in the rap game. Starting off in the early 90’s under the name Common Sense, the Chicago rapper has released a string of classics over the years, dabbling in a variety of sounds and genres.
Favorite Song by Common: “I Used to Love H.E.R.” from 1994’s Resurrection is a jazzy and socially conscious hip-hop anthem which decries the popular gangster lyrics of the day and calls for a return to thoughtful lyricism.
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2. Da Brat
Da Brat’s name as a rapper might not come up as often as others on this list, but she could hold her own with the best male MCs. With her 1994 classic Funkdafied becoming the first album by a solo female hip-hop artist to go platinum, it’s a wonder her influence isn’t discussed more often.
Favorite Song by Da Brat: “Funkdafied,” the title track of her classic album, is a smooth and funky G-funk party jam.
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3. No I.D.
Often called “The Godfather of Chicago Hip-Hop,” No I.D. had a crucial impact on the Chicago scene and the hip-hop scene at large, influencing guys like Kanye West in the process. His 1997 album Accept Your Own and Be Yourself (The Black Album) is a classic that often gets overlooked since No I.D. is more known for his production work nowadays.
Favorite Song by No I.D.: “Sky’s the Limit,” the single from his 1997 album, is a laid back yet uplifting jam that shows No I.D.’s impeccable and relaxed flow.
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4. Lupe Fiasco
Lupe Fiasco is a Chicago rapper who took Common’s advice to heart and has primarily focused on socially conscious and politically aware lyricism. Combining these aspects with his unique musical choices makes Lupe Fiasco one of the modern greats.
Favorite Song by Lupe Fiasco: “Kick, Push” from 2006’s Food and Liquor is a thrilling and bold choice for a lead single. This song tells a unique love story for hip-hop.
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5. Chance the Rapper
While the bulk of Chance’s output has been spotty, his 2013 mixtape Acid Rap is so good that he deserves a seat at the table. This experimental release lives up to its name, with Chance citing LSD as a crucial component of the album’s production.
Favorite Song by Chance the Rapper: “Cocoa Butter Kisses” is an excellent collaboration with Vic Mensa and Twista. A trippy and jazz-influenced track, this is Chance’s finest moment.
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6. R.A.P. Ferreira
If you haven’t kept up with hip-hop in a while, you might know Ferreira better by his old name Milo. Whatever name the guy goes by, he keeps delivering experimental and cutting edge hip-hop time and time again, further demonstrating that Chicago hip-hop is always about looking forward.
Favorite Song by R.A.P. Ferreira: “An Idea Is a Work of Art” from 2020’s Purple Moonlight Pages shows that the artist formerly known as Milo just keeps on getting better. I’m a sucker for jazz-influenced hip-hop.
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7. Open Mike Eagle
One of the alternative hip-hop artists who inspired guys like R.A.P. Ferreira is Open Mike Eagle, who has consistently released top notch records for the past decade. He’s got a great sense of humor, but his beats and delivery are no joke whatsoever.
Favorite Song by Open Mike Eagle: “Thirsty Ego Raps” from 2014’s Dark Comedy is probably not the “best” Open Mike Eagle song, but it’s what I’d call a perfect example of his style if you’re a newcomer. Filled with random and goofy lyrics that make more sense with repeated listens, it’s a song I keep coming back to.
8. Chief Keef
I’m normally not a fan of trap or mumble rap, but Chief Keef just consistently produces fun and catchy party music, and he’s undeniably one of the biggest names in Chicago rap today. He was dropping his first tracks when I was in high school, so his music is a large part of the party soundtracks of that era. He’s great at what he does.
Favorite Song by Chief Keef: “3Hunna” is a silly, brash, over-the-top song featuring Rick Ross, but it’s an addictive party song. I love the fun club atmosphere.
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Going back to the old school for a bit, Twista (formerly known as Tung Twista) is one of the OGs of Chicago rap music, influencing many who would come later. While he hasn’t been as prolific in recent years, his 90’s and early 2000’s run of albums cemented him as one of the greats.
Favorite Song by Twista: “Death Before Dishonor” is just a killer gangsta rap track from 1997’s Adrenaline Rush. It’s a great juxtaposition to what Twista’s friend and colleague Common was releasing around the same time, showing the diversity of the Chicago scene.
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Qwel is an experimental white rapper from Chicago who mixes abstract beats and lyrics with political and philosophical elements as well. While the man might look more like an accountant than a rapper, he’s got such a unique voice that it’s a shame Qwel has largely remained an underground rapper.
Favorite Song by Qwel: “Underachiever” is the first song that comes to mind, with its spacey and jagged rhythms underneath Qwel’s unique and deadpan delivery.
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Vakill’s work with hip-hop collective The Molemen is worth a listen, but I think he rose to the level of the greats as a solo artist in the early 2000’s. His name doesn’t come up much nowadays, but 2003’s The Darkest Cloud is a refreshing and thoughtful album in the Chicago rap world.
Favorite Song by Vakill: “Til the World Blows Up” is a laid back and jazzy track, but really any song on The Darkest Cloud is great. The beats incorporate elements of piano-driven jazz, while Vakill remains engaging and clever throughout.
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12. Fredo Santana
While Fredo Santana sadly passed away in 2018 before he could fully realize his potential, he left us with some great stuff in the meantime. While often known for his association with Chief Keef, I personally think Fredo produced music that was more forward-thinking and experimental, incorporating Memphis horror elements with the trap and drill party style Keef is known for.
Favorite Song by Fredo Santana: “Trap Life” is a fist-pumping anthem from 2013’s mixtape Fredo Kruger, its horrorcore elements an obvious homage to acts like Three 6 Mafia.
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Like Chance, R.A.P., and the late Fredo, Saba is another young cat at the forefront of the Chicago rap scene. Saba has the alternative and jazz elements of his peers while also incorporating strong traces of soul. This gives Saba’s music a unique sensitivity and vulnerability to it.
Favorite Song by Saba: “Church (Liquor Store),” from Saba’s 2016 debut Bucket List Project is a laid back, chilled out, jazzy exercise while Saba lays down his unique and powerful enunciations. I love the range of emotions Saba can explore with his voice, acting out his words in a sense.
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Noname is a young female rapper who takes a different approach from Da Brat—Noname’s music is more soulful, jazzy, and poetically oriented. Her 2018 album Room 25 is a fantastic release that stands up there with the work of her colleagues like Chance and R.A.P.
She comes from the slam poetry scene, so spoken word and an emphasis on lyricism often takes precedence over the beats, but her music often has an enchanting effect nonetheless.
Favorite Song by Noname: “Ace” is a great collaboration featuring Saba. Both artists get to show off their tremendous talent here, yet Noname’s great lyrics and unique style steal the show.
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15. Kanye West
It makes sense I’d save arguably the biggest name in rap (and pop music as a whole) of the last twenty years for last on this list—Kanye’s appeal is so far and wide that many might have stopped reading after his name, as even people who aren’t fans of rap listen to Kanye.
Whatever you think of the man himself, West’s ability to transcend genres and to blend so many elements together has made his music a cultural mainstay of our times. While recent releases have been disappointing, West had a nearly impeccable discography from around 2004 to 2015 or so.
Favorite Song by Kanye West: “Champion” comes from 2007’s Graduation. While not my favorite Kanye West album, I love this song—the sample of Steely Dan’s “Kid Charlemagne” works so well with the lyrics about West’s father. Also, if you’re looking for sad Kanye West songs, or maybe just reflective ones, I’d recommend “Street Lights.:
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Wrapping It Up
There you have it, fifteen names of the best Chicago rappers, ranging from the originals of the old school to the torchbearers and trailblazers of the modern age. While I’m sure you’re familiar with at least a couple names on this list, I urge you to check out the names you don’t recognize if you want to explore some of the great gems of Chicago rap out there.
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This article was written by Avery and edited by Michael.