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.