The Best Chicago Rappers You Haven’t Heard Of

A List Of Chicago’s Best Under-The-Radar Rappers

Chicago has always been an important city for music. From the blues and jazz to house and drill rap, the Windy City has sparked some of the most vital creative movements in the history of music while also boasting some of the best musicians in the world.

Chi-Town has a long history of great music and the city has been making its mark on the hip-hop scene for decades. From Common and Kanye to Chance The Rapper and Chief Keef to Mick Jenkins and Open Mike Eagle, the Windy City has birthed some of the most respected and influential rappers around. And it continues to give rise to exciting new rappers who are worth checking out if you’re interested in expanding your musical horizons.

Broadly speaking, today’s Chicago rap scene is one of the most exciting and fresh in the world, producing some of the most innovative and exciting music around. Chicago’s new school rappers are breaking boundaries with their music, experimenting and creating new sounds that are unlike anything else coming out in the south, midwest, west or east coasts of the country.

With the constant influx of new talent in Chicago, it can be difficult to sift through everything and find artists that are truly worth your time. So with that in mind, Endless Crate has put together a list of the best under-the-radar Chicago rappers, artists who are creating exciting sounds for hip-hop heads of all ages.

Vic Spencer

Vic Spencer has spent the last decade or so steadily building a cult following with his raw and unapologetic approach to rap music. And yet, despite his exceptional output his work is largely overlooked by mainstream audiences, thanks in part to his steadfast commitment to self-releasing his music and his aversion to traditional rap structures.

Whether dropping rewind-worthy punchlines or stories about the Chicago-area locations he knows best, Vic Spencer has long been one of hip-hop’s most potent combinations of intellect and entertainment. Among the upper echelon of Chicago rappers, he keeps pushing his own boundaries from album to album with a conviction that only comes from someone truly devoted to their art form. Focusing less on mainstream success than he does on keeping his name in the underground hip-hop headlines, Vic has collaborated with rap royalty like Sean Price, 38 Spesh, Flee Lord, and Chicago’s own Tree, as well as working with new faces who might not be household names just yet. Case in point: Mudslide, his 2022 collaborative album with rising Philly producer Small Professor.

Mother Nature

Chicago’s hip-hop scene has always been an eclectic mix of sounds, and Mother Nature have carved out their own iconoclastic lane that’s cemented them as one of the next acts to come out of the Windy City. The duo, comprised of Chicago rappers Klevah and TRUTH, combine for powerful rhymes that pierce the conscience. While they’re often praised for their skillful wordplay, it’s their chemistry that truly sets them apart as a duo. Mother Nature’s music blends a wide variety of sounds and styles – from smooth g-funk to abstract trap to futuristic boom bap – but at its core are two emcees with a penchant for depth. Both Klevah and TRUTH deliver bars in a layered cadence that’s agile and nimble as they effortlessly shift between styles and tempos in the same song. Their music is a refreshing departure from the familiar rap tropes that permeate mainstream hip-hop today; instead, they deliver an honest and heart-felt experience that breathes new life to the genre.

Rich Jones

In the short time since he started rapping, Rich Jones has become one of Chicago’s most beloved artists. Driven by the search for new sounds, Jones’ unique style succeeds in equal parts because of its lyricism and production quality. An integral part of Chicago’s rap scene since he first picked up the mic, Jones has teamed with some of the best Chicago rappers around, including Joshua Virtue and Defcee (more on them later), to create tightly focused tracks which blend autobiography and social commentary. On his latest album Smoke Detector he worked entirely with producer Iceberg Theory to create one of the most eclectic and interesting hip-hop albums of 2022.


Lighting up the underground rap scene since the early 2010s when he was a member of Chicago’s Tomorrow Kings collective, SKECH185 is one of the most formidable rappers out these days. He makes music that feels vital and urgent. His flow is clear and direct, and his delivery is pure wreckage, like an engine running so hot it’s about to burst into flames. His sound is claustrophobic and he fills every verse with complex lyrics that have you rewinding to figure out what he said.

Now based in New York, SKECH185 has put his voice on some of the most exciting rap projects of the past few years, including guest verses for Armand Hammer and his flawless 2023 collaborative album with producer Jeff Markey, He Left Nothing For The Swim Back. A vital artist who should be a big name soon, SKECH is just waiting for the rest of the world to catch up with him.

Related: SKECH185 & Jeff Markey – He Left Nothing For The Swim Back Album Review


Defcee is a Chicago-based rapper and educator whose distinctive, forceful flow have made him one of the best rappers in the midwest. Although he’s only been performing in the music scene for a relatively short while, Defcee has already made a name for himself as one of the most exciting new rappers to come out of Chicago in a minute. His finesse and top-notch beat selection make him an MC who pushes the boundaries of lyrical composition. He’s worked relentlessly on crafting a dope sound centered around masterful flows, multi-syllabic acrobatics and strong production. With complex rhymes, insightful lyrics and cutting-edge production from producers like BoatHouse, Spectacular Diagnostics and Televangel, Defcee has created a buzz in underground circles with his vaulting lyricism and undeniable bravado.


Known best for producing tracks for Chicago rappers like Mick Jenkins and Qari, GreenSllime has been a cult favorite in Chi-town for years. In addition to working as a rapper, producer and DJ, he hosts his own talk show on YouTube (Sllime’s Broke Ass Low Budget Show) where he interviews other Chicago creatives/friends like Smino and Saba. While GreenSllime has established himself as a producer and presenter, he’s really come into his own as a solo artist lately with a slew of stellar self-released projects. GreenSllime’s lyrics are blunt and crass, and his solo sound is a signature blend of dusty samples and boom-bap drum patterns. It pays homage to classic grimy hip-hop, but it also pushes boundaries and expectations by infusing other influences into the mix. Among Chicago rappers, GreenSllime is definitely one to watch.

Psalm One

Chicago’s hip-hop scene has seen many artists come and go, but Psalm One is one who’s kept on going. The Chicago rapper and educator has been making her mark on the music scene for decades now. Known for her thoughtful lyrics, and commanding stage presence, she cemented her genre blending skills and multi-faceted appeal straight out of the gate with her 2002 debut album Bio:Chemistry, which she released while studying chemistry at the University of Illinois. Bay Area rapper Casual (of Hieroglyphics fame) discovered her talents shortly after and she later became the first female artist to ink a deal with Rhymesayers Entertainment.

A regular fixture in both the hip-hop and public educational spheres of Chicago, Psalm One has used her platform to spread appreciation for the art of lyricism to future generations, including running a hip-hop influenced after school program called Rhymeschool. As a rap artist, she’s heralded for her fierce lyrical craft, tough beat selection and message of social justice and community building.

For a good entry point into Psalm’s stellar catalogue, check out her 2022 album Bigg Perrm.

Joshua Virtue

Despite being a relatively new and upcoming artist, Joshua Virtue has put out more music in his career than many artists twice his age. With five full-length albums already under his belt and numerous features, as well as two released with Chicago rapper Davis as the duo UDABABY, Virtue is one of the most prolific and musically impressive Chicago rappers working today.

There’s much more to Virtue’s music than meets the eye. A rapper who creates music that demands to be heard, his singular sound is at the intersection of rap in its most experimental form. His production is a level up, with a sound that’s challenging yet enjoyable, and his solo work explores a wide range of topics.

While all of Virtue’s releases have been prolific, 2022’s RAMA is his most fully realized project to date, taking his sonic experimentation to another place entirely and offering up one of the most uniquely crafted albums to come out in quite some time.


If you want to hear a rapper who knows how to turn a phrase like nobody else, look no further than Davis. An MC capable of spitting venom and sarcasm, Davis has already established himself as an important part of Chicago’s hip-hop scene. Though his popularity is growing rapidly, he’s remained true to his roots as an artist dedicated to bringing a fresh perspective to the art form. In addition to his solo work, he cofounded Why? Records in 2019 with fellow MCs Malci, Ruby Watson and Joshua Virtue (who he also performs alongside as the duo UDABABY). Each of his solo projects provide a snapshot into what has made him one of the most exciting Chicago rappers around, with deft wordplay and punchy beats that make it clear Davis is working at building a sound that’s all his own.


Few hip-hop acts are capable of weaving together words and sound in a way that touches listeners down to the core. Jyroscope is one of them. The Chicago duo of IB Fokuz and Collasoul Structure mixes soulful beats with lyrics that reflect daily life from a different perspective. In many ways, Jyroscope has a lot in common with their hometown peers: the group doesn’t fit into a neat category, and that’s part of the reason they’re one of Chi-Town’s greatest groups. From lyrical flow to beats that are the perfect mix of nostalgia and futuristic production, Jyroscope create a raw sound for hardcore hip-hop heads. IB Fokuz and Collasoul Structure are two of Chicago’s most versatile MCs, both equally adept at freestyling or laying down bars over laidback beats. IB Fokuz constantly stays on top of his lyrical game and Collasoul Structure proves why he’s one of Chicago’s finest emcees with clean flows, witty punchlines and vivid storytelling.

Related: Midwest Rappers You Should Be Listening To