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!

list ordered by

1
+ - 1,605 660
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 Old School Anime From 1999 and Before

2
+ - 1,433 762
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

3
+ - 1,012 516
Common is listed (or ranked) 3 on the list The Best Chicago Rappers
Common Resurrection, Be, Like Water for Chocolate

4
+ - 1,277 667
Chief Keef is listed (or ranked) 4 on the list The Best Chicago Rappers
Chief Keef Finally Rich, Back From the Dead, I Don't Like

5
+ - 1,037 535
Lupe Fiasco is listed (or ranked) 5 on the list The Best Chicago Rappers
Lupe Fiasco Food & Liquor, Food & Liquor II: The Great American Rap Album, Part 1

6
+ - 1,115 543
G Herbo is listed (or ranked) 6 on the list The Best Chicago Rappers
G Herbo

7
+ - 862 434
Twista is listed (or ranked) 7 on the list The Best Chicago Rappers
Twista Adrenaline Rush, Kamikaze, The Day After

8
+ - 785 347
Vic Mensa is listed (or ranked) 8 on the list The Best Chicago Rappers
Vic Mensa Innanetape, Straight Up, Down on My Luck

9
+ - 914 444
Lil Bibby is listed (or ranked) 9 on the list The Best Chicago Rappers
Lil Bibby

10
+ - 532 198
Montana of 300 is listed (or ranked) 10 on the list The Best Chicago Rappers
Montana of 300 Cursed With a Blessing, Gunz n Roses, Fire in the Church

11
+ - 936 506
Lil Durk is listed (or ranked) 11 on the list The Best Chicago Rappers

12
+ - 674 327
Mick Jenkins is listed (or ranked) 12 on the list The Best Chicago Rappers
Mick Jenkins

13
+ - 611 270
Earl Sweatshirt is listed (or ranked) 13 on the list The Best Chicago Rappers
Earl Sweatshirt Earl, Doris, Chum

14
+ - 513 243
Tink is listed (or ranked) 14 on the list The Best Chicago Rappers
Tink

15
+ - 483 229
SZA is listed (or ranked) 15 on the list The Best Chicago Rappers
SZA Z, See.SZA.Run EP, S EP

The Best Songs About Chicago Songs That Were Total Ripoffs

16
+ - 493 239
Da Brat is listed (or ranked) 16 on the list The Best Chicago Rappers
Da Brat Funkdafied, Unrestricted, Miss P.

17
+ - 441 225
Rhymefest is listed (or ranked) 17 on the list The Best Chicago Rappers
Rhymefest Blue Collar, Mark Ronson Presents Rhymefest: Man in the Mirror, Raw Dawg

18
+ - 370 168
Crucial Conflict is listed (or ranked) 18 on the list The Best Chicago Rappers
Crucial Conflict The Final Tic, Good Side Bad Side, Planet Crucon

19
+ - 605 317
Fredo Santana is listed (or ranked) 19 on the list The Best Chicago Rappers
Fredo Santana It's A Scary Site

20
+ - 299 125
Do or Die is listed (or ranked) 20 on the list The Best Chicago Rappers
Do or Die Pimpin Ain't Dead, D.O.D., Back 2 the Game

21
+ - 586 302
Lil Reese is listed (or ranked) 21 on the list The Best Chicago Rappers
Lil Reese Supa Savage

22
+ - 515 282
King Louie is listed (or ranked) 22 on the list The Best Chicago Rappers
King Louie Showtime, My Hoes They Do Drugs, Your Pussy Is My Pillow

23
+ - 319 144
No I.d. is listed (or ranked) 23 on the list The Best Chicago Rappers
No I.d.

24
+ - 403 200
Chuck Inglish is listed (or ranked) 24 on the list The Best Chicago Rappers
Chuck Inglish Convertibles, Legs, Easily

25
+ - 496 299
L'a Capone is listed (or ranked) 25 on the list The Best Chicago Rappers
L'a Capone

26
+ - 405 205
Ca$his is listed (or ranked) 26 on the list The Best Chicago Rappers
Ca$his The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

27
+ - 374 186
Brandun DeShay is listed (or ranked) 27 on the list The Best Chicago Rappers
Brandun DeShay All Day DeShay: AM, Volume: Three! To Get Ready

28
+ - 374 188
Gil Scott-Heron is listed (or ranked) 28 on the list The Best Chicago Rappers
Gil Scott-Heron Bridges, Winter in America, The First Minute of a New Day

29
+ - 396 175
Kids These Days is listed (or ranked) 29 on the list The Best Chicago Rappers
Kids These Days Traphouse Rock, All These Interruptions, Manifest Destiny

The Greatest Rappers of All Time Things You Should Stop Apologizing For

30
+ - 366 186
Rockie Fresh is listed (or ranked) 30 on the list The Best Chicago Rappers
Rockie Fresh The Otherside Redux, Driving 88, The Otherside

31
+ - 354 184
Juice is listed (or ranked) 31 on the list The Best Chicago Rappers
Juice Something to Feel, Can We Get Personal?, Juice

32
+ - 326 161
Chris Ruben is listed (or ranked) 32 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

33
+ - 355 162
Kid Sister is listed (or ranked) 33 on the list The Best Chicago Rappers
Kid Sister Pro Nails Super High Shine EP, Ultraviolet, Control

34
+ - 322 171
Co-Still is listed (or ranked) 34 on the list The Best Chicago Rappers
Co-Still

35
+ - 322 185
Capital D is listed (or ranked) 35 on the list The Best Chicago Rappers
Capital D PolyMath, Insomnia, Return of the Renegade

36
+ - 311 163
Naledge is listed (or ranked) 36 on the list The Best Chicago Rappers
Naledge Chicago Picasso, The Kidz in the Hall Present: Naledge

37
+ - 295 195
Ty Money is listed (or ranked) 37 on the list The Best Chicago Rappers
Ty Money

38
+ - 292 196
Qwazaar is listed (or ranked) 38 on the list The Best Chicago Rappers
Qwazaar Walk Thru Walls

39
+ - 267 185
Sir Michael Rocks is listed (or ranked) 39 on the list The Best Chicago Rappers
Sir Michael Rocks

40
+ - 75 15
Young Pappy is listed (or ranked) 40 on the list The Best Chicago Rappers
Young Pappy

41
+ - 272 169
Legendary Traxter is listed (or ranked) 41 on the list The Best Chicago Rappers

42
+ - 275 198
Diverse is listed (or ranked) 42 on the list The Best Chicago Rappers
Tree One A.M., Wylin Out, Big Game

43
+ - 264 189
YP is listed (or ranked) 43 on the list The Best Chicago Rappers
YP

The Best Chicago Blues Songs The Best Video Game Franchises of All Time

44
+ - 272 181
Rastabwoykell is listed (or ranked) 44 on the list The Best Chicago Rappers
Rastabwoykell

45
+ - 250 163
Psalm One is listed (or ranked) 45 on the list The Best Chicago Rappers
Psalm One Bio:Chemistry II: Esters and Essays, The Death of the Frequent Flyer

46
+ - 70 18
Famous Dex is listed (or ranked) 46 on the list The Best Chicago Rappers
Famous Dex

47
+ - 241 184
Project Mayhem is listed (or ranked) 47 on the list The Best Chicago Rappers
Project Mayhem

48
+ - 262 177
Jeremiah Jae is listed (or ranked) 48 on the list The Best Chicago Rappers
Jeremiah Jae Raw Money Raps, Bad Jokes, New Day

49
+ - 257 177
Open Mike Eagle is listed (or ranked) 49 on the list The Best Chicago Rappers
Open Mike Eagle Unapologetic Art Rap, Rappers Will Die of Natural Causes, Sir Rockabye

50
+ - 244 171
Demarco Castle is listed (or ranked) 50 on the list The Best Chicago Rappers
Demarco Castle On the Road to Glory My Story