Chicago has been holding down the No. 1 spot as America’s third most populous city for a minute. So it shouldn’t be a surprise that the Windy City has housed more than a few of the most influential musicians to ever touch a stage. The likes of Quincy Jones, Chaka Khan, Sam Cooke, Nat King Cole and Herbie Hancock aren’t the only Chi-Town icons in existence. Chicago has also bred several hip-hop G.O.A.T.s. We all know Ye reps the Chi heavy, but did you know that the likes of Ludacris, Soulja Boy, Young Dolph and Earl Sweatshirt also have roots in the Chi? Chicago has played a major role in shaping what modern hip-hop music and culture looks and feels like. From ushering in drill music to being a hub for super more conscious, lyrical, backpack type rap to birthing some of music’s biggest superstars, Chicago has been a force to be reckoned with. But who are the best Chicago rappers of all time?
Let’s take a look at the best of the best of Chicago’s top-tier MCs. These are the 16 best Chicago rappers of all time.
To start off our list of the best Chicago rappers, we’ve got Calboy—a rapper who’s made a name for himself for the right reasons. If you’re new to Calboy, even though you’re not early, here’s your chance to get hip. You can thank us later. Chances are, you’ve heard his song “Envy Me”—which has over 200 million views on YouTube.
It goes without saying that Lucki deserves a spot on this list. After all, he’s spent the last several years on a graceful come-up, and he’s finally got the type of attention he’s been deserving for the longest. Check out some of his latest, it’s heat.
If you’re into hip-hop that comes with a dash of introspection, then Saba is your guy. This dude weaves intricate lyrics with beats that’ll have you tapping your feet in no time. It’s not just music, it’s an experience – a journey into the heart of the West Side of Chicago.
At number nine, we’ve got Noname, the insightful poetess of the Chicago scene. She’s got a style that’s both soulful and sweet, with lyrics so rich they feel like a meal. Her intellectual approach to rap sets her apart and is definitely worth your time. It’s not about bling or bravado with Noname—it’s about storytelling, and man, can she spin a tale.
Lil Durk’s twin made a name for himself with hard-hitting anthems like “Took Her To The O” and “Crazy Story”. King Von’s music embodied the gritty spirit of his hometown. King Von’s legacy will continue to live on through his music, which will remain timeless for generations to come.
Da Brat is a legend. Known for her style and flow, the So So Def artist became the first solo female rapper to go platinum, with her 1994 album, Funkdafied.
G Herbo is a hometown legend. He first made noise in the early 2010s with projects like 2014’s Welcome to Fazoland. He has since released several albums and mixtapes, including 2017’s Humble Beast and 2019’s PTSD. He has collaborated with the likes of Nicki Minaj, Lil Durk and 21 Savage. G Herbo continues to carve out his lane.
At number five, we’ve got Twista, a true pioneer in the game. Known for his lightning-fast lyrical style, Twista held the Guinness World Record as the fastest rapper. He’s not just quick though, he’s also got a flow so smooth you could skate on it.
Now, Polo G, he’s the one to watch. Bursting onto the scene with his single “Finer Things,” this young talent has quickly risen to the top with his emotional and gritty take on drill music. He’s got a depth of feeling in his music that tugs at the heartstrings while still getting you to bob your head to the beat.
Lupe Fiasco, a staple of Chi-town’s rap scene, has consistently delivered lyrically rich and deeply personal songs since his debut. With his cool, laid-back style and his boundary-pushing themes, Lupe has carved out a unique spot for himself in hip-hop.
Chance is like that cool kid from school who also happens to be incredibly talented. His music is quirky, catchy, and thoughtful. Who could forget Coloring Book, which nabbed him a well-deserved Grammy? This man’s not just a rapper, he’s a movement, shaking up the music industry with his independent approach.
Long Live Juice Wrld. The young G.O.A.T. made an impact on the game in such a short amount of time. He rose to fame with the hit song “Lucid Dreams” in 2018 and continued to up it with albums such as Goodbye & Good Riddance, Wrld on Drugs (with Future) and Death Race for Love.
Lil Durk is one of those artists who came up from the trenches and made it big without forgetting where he came from. Durk’s music is filled with raw emotion and stark narratives of his life growing up in Chicago. Over time, he has evolved his style, infusing melodic elements into his street-inspired sound. He’s more than a rapper—he’s a symbol of perseverance and resilience. And hey, he’s got the co-signs from industry heavyweights like Drake and Kanye, which speaks volumes.
Chief Keef, the godfather of drill music. This man’s influence on Chicago’s rap scene is indisputable. His raw and unfiltered style defined a generation and brought the city’s South Side to the global stage. For better or worse, Keef changed the game and his impact continues to resonate.
No. 2 is none other than the soulful, eloquent Common. This man is like the philosopher of Chicago’s rap scene. From love and life to social issues, Common raps about it all. His songs are timeless, his flow is unmatched, and his influence on hip-hop is monumental. He’s easily one of the greatest Chicago Rappers of all time.
And who else could top our list of best Chicago rappers but the controversial, the innovative, the one and only, Kanye West. Love him or hate him, you can’t deny his influence on the rap scene. Kanye’s experimental beats and heartfelt lyrics have made him one of the most successful artists of all time. From “College Dropout” to “Donda”, Ye has remained a central figure in hip-hop, pushing the envelope and keeping us all on our toes.
