100 Chicago Rappers & Artists Worth Listening To

100 Chicago Rappers & Artists Worth Listening To

It’s been a few years since the last Chicago Rappers/Artists List and there have been a plethora of artists that have made their presence felt on the hip hop scene since then. From mainstream successes such as Juice WRLD and Polo G to burgeoning underground artists like Duffle Bag Buru and Nnamdi Ogbonnaya, there are plenty of styles to be found here. With sounds ranging from hard hitting bangers to introspective experimentalism, Chicago has nearly every flavor of hip hop you could imagine and I tried to include a little bit of everything in this snapshot. Featuring entirely new artists from the last list, this selection of Windy City talent proves just how prolific and vibrant this musical community is. While it does have 100 Chicago rappers/hip hop artists, this list is by no means an all-encompassing look at the genre in the city and there are bound to be skilled artists I failed to mention.

On top of the list itself, I put together a playlist with my favorite track from each artist. Check out all 100 rappers/artists below, along with the playlist, and get in tune with what Chicago has been putting out.

This list has no repeats from the previous list. If your favorite Chicago artist isn’t on this one, there’s a very good chance they were on the last one.

This is in no particular order.

100 Rappers/Artists Playlist

Juice WRLD


If you haven’t heard of Juice WRLD yet, you probably haven’t been paying attention to hip hop much recently. The young Chicago artist has burst onto the scene and is one of music’s biggest rising stars with huge Billboard hits and collaborations with artists such as Future.

Polo G


Polo G is another rising Chicago star and has caught the attention of big publications such as XXL. With music full of true-to-life topics combined with high quality production and catchy vocals, Polo G has a well-rounded sound that is taking him big places.

Queen Key


With multiple hits under her belt already, Queen Key is poised to be one of the genre’s biggest artists. Fun music and bringing women to the forefront are both a big part of Queen Key’s image and they are both helping her reach a new level.



Poised for the limelight, Calboy has been seeing his stock rise considerably thanks to his consistently dope music. From interviews with Billboard to an abundance of streams online, things are looking up for this skilled MC.

Duffle Bag Buru


From his high quality music to his strong presence on the Chicago scene, Duffle Bag Buru has been making a name for himself over the past year or so and people are starting to pay attention. With production from some of the city’s best beatsmiths, Buru has been making all the right moves and we expect him to be a staple in the underground in no time.

Lil Zay Osama


With multiple hits under his belt already, Lil Zay Osama is looking like one of the city’s best artists on the rise. Tracks like Changed Up and Pain are good examples of the music he provides and show how much talent he has.



To put it bluntly, Chicago is packed with talented hip hop artists. While the scene is crowded, ICYTWAT has proven to be a force in the Windy City thanks to his highly interesting, catchy music that is a divergence from the typical hip hop sound. Full of melancholy, extremely confident concepts, ICYTWAT has shown that he makes music he likes and it doesn’t matter if that’s different from what’s trending at the moment.




There are a few superstars already on the Chicago scene and Dreezy is definitely one of them. The Interscope signee was named the Princess of Chicago Rap and has put out multiple solid projects over the past few years.

Z Money


A Chicago vet, Z Money has been making waves for quite some time and has become a big figure on the scene. One of the city’s dopest and most recognizable artists, his presence is felt all over and has earned the respect he is given.

Stark Of Huey


One of the Westside’s most promising artists, Stark of HUEY has shown consistency with his music and continues to be a leader for HUEY Gang, a Chicago collective of aspiring MCs. His strong melodies and harmonies have helped set him apart from the crowd.




3 thoughts on “100 Chicago Rappers & Artists Worth Listening To

Leave a Reply

%d bloggers like this: