bands/musicians The Best Chicago Rappers  

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List Rules Only famous hip hop artists from Chicago.

When you think of Chicago rappers these days, the first person that usually comes to mind is Kanye West. While he is from the Windy City, immensely famous and critically lauded, there is so much more to the Chicago hip hop scene. So much so that it couldn’t possibly all be included here. This is a list of the best Chicago rappers, ranked by hip hop fans.

Chicago rappers take their inspiration from every part of the country – some embraced the East coast, others, the West coast, and still others, the South. While there is no actual “Chicago sound” there is still a unique voice and seemingly limitless talent. Check out these rappers from Chicago and vote for your favorite, and while you’re at it, add your own voice to the mix! If anybody is missing, add them!

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Chance The Rapper is listed (or ranked) 1 on the list The Best Chicago Rappers
Chance The Rapper Acid Rap, Confident, Songs from Scratch: Paranoia

The Greatest White Rappers of All Time The Best Scottish Actors of All Time

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Kanye West is listed (or ranked) 2 on the list The Best Chicago Rappers
Kanye West My Beautiful Dark Twisted Fantasy, Late Registration, The College Dropout

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Lupe Fiasco is listed (or ranked) 3 on the list The Best Chicago Rappers
Lupe Fiasco Food & Liquor, Food & Liquor II: The Great American Rap Album, Part 1

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Common is listed (or ranked) 4 on the list The Best Chicago Rappers
Common Resurrection, Be, Like Water for Chocolate

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Chief Keef is listed (or ranked) 5 on the list The Best Chicago Rappers
Chief Keef Finally Rich, Back From the Dead, I Don't Like

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Twista is listed (or ranked) 6 on the list The Best Chicago Rappers
Twista Adrenaline Rush, Kamikaze, The Day After

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G Herbo is listed (or ranked) 7 on the list The Best Chicago Rappers
G Herbo

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Montana of 300 is listed (or ranked) 8 on the list The Best Chicago Rappers
Montana of 300 Cursed With a Blessing, Gunz n Roses, Fire in the Church

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Vic Mensa is listed (or ranked) 9 on the list The Best Chicago Rappers
Vic Mensa Innanetape, Straight Up, Down on My Luck

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Earl Sweatshirt is listed (or ranked) 10 on the list The Best Chicago Rappers
Earl Sweatshirt Earl, Doris, Chum

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Lil Bibby is listed (or ranked) 11 on the list The Best Chicago Rappers
Lil Bibby

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Mick Jenkins is listed (or ranked) 12 on the list The Best Chicago Rappers
Mick Jenkins

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Lil Durk is listed (or ranked) 13 on the list The Best Chicago Rappers

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Da Brat is listed (or ranked) 14 on the list The Best Chicago Rappers
Da Brat Funkdafied, Unrestricted, Miss P.

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Rhymefest is listed (or ranked) 15 on the list The Best Chicago Rappers
Rhymefest Blue Collar, Mark Ronson Presents Rhymefest: Man in the Mirror, Raw Dawg

The Best Songs About Chicago Songs That Were Total Ripoffs

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Crucial Conflict is listed (or ranked) 16 on the list The Best Chicago Rappers
Crucial Conflict The Final Tic, Good Side Bad Side, Planet Crucon

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Do or Die is listed (or ranked) 17 on the list The Best Chicago Rappers
Do or Die Pimpin Ain't Dead, D.O.D., Back 2 the Game

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Tink is listed (or ranked) 18 on the list The Best Chicago Rappers
Tink

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SZA is listed (or ranked) 19 on the list The Best Chicago Rappers
SZA Z, See.SZA.Run EP, S EP

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Ca$his is listed (or ranked) 20 on the list The Best Chicago Rappers
Ca$his The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

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No I.d. is listed (or ranked) 21 on the list The Best Chicago Rappers
No I.d.

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Brandun DeShay is listed (or ranked) 22 on the list The Best Chicago Rappers
Brandun DeShay All Day DeShay: AM, Volume: Three! To Get Ready

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Chuck Inglish is listed (or ranked) 23 on the list The Best Chicago Rappers
Chuck Inglish Convertibles, Legs, Easily

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Fredo Santana is listed (or ranked) 24 on the list The Best Chicago Rappers
Fredo Santana It's A Scary Site

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King Louie is listed (or ranked) 25 on the list The Best Chicago Rappers
King Louie Showtime, My Hoes They Do Drugs, Your Pussy Is My Pillow

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Kids These Days is listed (or ranked) 26 on the list The Best Chicago Rappers
Kids These Days Traphouse Rock, All These Interruptions, Manifest Destiny

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Gil Scott-Heron is listed (or ranked) 27 on the list The Best Chicago Rappers
Gil Scott-Heron Bridges, Winter in America, The First Minute of a New Day

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Chris Ruben is listed (or ranked) 28 on the list The Best Chicago Rappers
Chris Ruben Coffee & Vinyls - CHICAGO | Beat Maker | MC | Amateur Photographer | Instagram: CHRISRUBEN_ | 3AM | Booking: djceasedays@gmail.comsoundcloud.com/chris_ruben

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Juice is listed (or ranked) 29 on the list The Best Chicago Rappers
Juice Something to Feel, Can We Get Personal?, Juice

The Greatest Rappers of All Time Harsh Reminders Every 30-year-old Needs to Hear Right Now

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Lil Reese is listed (or ranked) 30 on the list The Best Chicago Rappers
Lil Reese Supa Savage

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Rockie Fresh is listed (or ranked) 31 on the list The Best Chicago Rappers
Rockie Fresh The Otherside Redux, Driving 88, The Otherside

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Kid Sister is listed (or ranked) 32 on the list The Best Chicago Rappers
Kid Sister Pro Nails Super High Shine EP, Ultraviolet, Control

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Co-Still is listed (or ranked) 33 on the list The Best Chicago Rappers
Co-Still

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L'a Capone is listed (or ranked) 34 on the list The Best Chicago Rappers
L'a Capone

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Capital D is listed (or ranked) 35 on the list The Best Chicago Rappers
Capital D PolyMath, Insomnia, Return of the Renegade

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Naledge is listed (or ranked) 36 on the list The Best Chicago Rappers
Naledge Chicago Picasso, The Kidz in the Hall Present: Naledge

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Qwazaar is listed (or ranked) 37 on the list The Best Chicago Rappers
Qwazaar Walk Thru Walls

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Ty Money is listed (or ranked) 38 on the list The Best Chicago Rappers
Ty Money

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Diverse is listed (or ranked) 39 on the list The Best Chicago Rappers
Tree One A.M., Wylin Out, Big Game

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YP is listed (or ranked) 40 on the list The Best Chicago Rappers
YP

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Sir Michael Rocks is listed (or ranked) 41 on the list The Best Chicago Rappers
Sir Michael Rocks

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Legendary Traxter is listed (or ranked) 42 on the list The Best Chicago Rappers

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Rastabwoykell is listed (or ranked) 43 on the list The Best Chicago Rappers
Rastabwoykell

The Best Chicago Blues Songs Cute Ways to Ask Someone to Prom

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Project Mayhem is listed (or ranked) 44 on the list The Best Chicago Rappers
Project Mayhem

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+ - 259 163
Jeremiah Jae is listed (or ranked) 45 on the list The Best Chicago Rappers
Jeremiah Jae Raw Money Raps, Bad Jokes, New Day

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Psalm One is listed (or ranked) 46 on the list The Best Chicago Rappers
Psalm One Bio:Chemistry II: Esters and Essays, The Death of the Frequent Flyer

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Open Mike Eagle is listed (or ranked) 47 on the list The Best Chicago Rappers
Open Mike Eagle Unapologetic Art Rap, Rappers Will Die of Natural Causes, Sir Rockabye

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+ - 243 156
Demarco Castle is listed (or ranked) 48 on the list The Best Chicago Rappers
Demarco Castle On the Road to Glory My Story

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Treated Crew is listed (or ranked) 49 on the list The Best Chicago Rappers
Treated Crew

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+ - 234 155
JaMiss is listed (or ranked) 50 on the list The Best Chicago Rappers