100 Chicago Rappers & Artists Worth Listening To

100 Chicago Rappers & Artists Worth Listening To

Sydny August


The city’s North Side has been getting more and more attention thanks to artists like Sydny August. The Chicago songstress has performed at classic venues such as Double Door and The Metro and continues to show the city just how talented she is.



The Save Money team has deep roots and artists like Brill are a part of their electrifying ecosystem. The R&B crooner has the singing chops and smooth style to make a name for himself on a larger scale than just Chicago.

Realest JBone


It can be easy to get lost in the shuffle with the abundance of artists in Chicago, but Realest JBone has made connections and music that should change that soon. Working with the likes of Mvjor and Meechie Greedy helped him land a Fetty Wap placement and it looks like he has more to come soon.

Morocco Brown


Employing a creative  flow and a sound that loosely resembles some of Chicago’s finest such as Chance The Rapper, Morocco Brown has been on the come up for the past few years. His personal lyrics and interesting sound are things to check out when listening.



Some artists drop music all the time, others focus on perfecting their projects before releasing them. LEGIT is a part of the ladder group and that focused nature has helped him unleash fantastic full length projects such as Maudlin.



Taking a fresh twist on R&B, Schenay has found power in her vulnerability and uses those emotions to make heartfelt, passionate music that resonates with anyone who hears it. Be on the lookout for Schenay to become a key figure on the Chicago music scene.

Vic Spencer


Chicago has a vibrant underground scene and Vic Spencer probably belongs on the Chi-town underground Mount Rushmore at this point. His fame is well founded thansk to his songwriting and musical ability and he’s worked with prolific artists like Chance The Rapper and Future.

Lulu Be.


When she’s not making music she is the studio manager at Classick Studios which is also where she met producer Lanre who crafted the bouncy afrobeat infused production on her track Rude Tings. Her excellent mix of musical genres is sure to push her sound to a very broad audience.



Roo$ki has been one of the most well known names in Chicago’s underground for some years at this point, and there’s good reason for that. His brooding style and work with some of the most prominent producers in the city have made him a go-to artist on the scene.



It’s dope to see artists become part of such a strong community and AlifortheGo has collaborated with dozens of Chicago’s burgeoning artists. This sense of partnership has brought Ali to the forefront of the bubbling underground scene in the city.




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