From '90s pioneers like Common and Da Brat to transcendent superstars like Kanye West and Juice WRLD, these are the best rappers to come from the Windy City.
Dimas SanfiorenzoKool Keith
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Kanye West returned to Chicago with a bang, reuniting with Kid Cudi, and performing with Chief Keef, Don Toliver, Travis Scott, and many more.
Antonio Johri
From Drake and his new album 'Iceman' to Rod Wave who just released 'Don't Look Down'—we ranked the hottest rappers right now.
Dimas Sanfiorenzo
These are the best rap albums of 2026, featuring Drake's 'Iceman', Rod Wave's 'Don’t Look Down', and more.
Dimas SanfiorenzoLatest Stories
Premiere: L'Orange and Kool Keith Release the Video for "The Green Ray"
From their 'Time? Astonishing!' album.
Zach Frydenlund3940 days ago
Marvel Transforms Kendrick Lamar, Raekwon and Kool Keith Into Comic Book Characters
Marvel just released more hip-hop variants that turn Kendrick Lamar, Raekwon and Kool Keith into comic book characters.
Christopher Spata4019 days ago
Listen to Newly Unearthed Kool Keith, Slick Rick, and Wu-Tang Clan Freestyles From The 'Stretch And Bobbito' Archives
The legendary New York DJs have started unloading their archives on SoundCloud ahead of the documentary 'Stretch and Bobbito: Radio That Changed Lives.'
Trace William Cowen4089 days ago