bands/musicians The Best Chicago Rappers  

Ranker Hip Hop
Originally by
52.3k votes 6.4k voters 107.6k views 71 items Embed

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
2,064 1,032
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 51 Greatest Pictures of Animals Sitting Like People The Best Dressed Rappers

2
1,950 1,061
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
1,558 690
G Herbo is listed (or ranked) 3 on the list The Best Chicago Rappers
-1452106876343 added G Herbo

4
1,748 891
Chief Keef is listed (or ranked) 4 on the list The Best Chicago Rappers
JohnBerthiaume added Chief Keef Finally Rich, Back From the Dead, I Don't Like

5
1,177 494
Lil Bibby is listed (or ranked) 5 on the list The Best Chicago Rappers
-1452106876343 added Lil Bibby

6
913 329
Montana of 300 is listed (or ranked) 6 on the list The Best Chicago Rappers
PorzinGOD added Montana of 300 Cursed With a Blessing, Gunz n Roses, Fire in the Church

7
1,241 616
Lil Durk is listed (or ranked) 7 on the list The Best Chicago Rappers

8
1,239 668
Common is listed (or ranked) 8 on the list The Best Chicago Rappers
Common Resurrection, Be, Like Water for Chocolate

9
1,268 692
Lupe Fiasco is listed (or ranked) 9 on the list The Best Chicago Rappers
Lupe Fiasco Food & Liquor, Food & Liquor II: The Great American Rap Album, Part 1

10
1,009 550
Twista is listed (or ranked) 10 on the list The Best Chicago Rappers
NicholasDecowski added Twista Adrenaline Rush, Kamikaze, The Day After

11
1,023 445
Vic Mensa is listed (or ranked) 11 on the list The Best Chicago Rappers
Jasen Waslien added Vic Mensa Innanetape, Straight Up, Down on My Luck

12
650 356
L'a Capone is listed (or ranked) 12 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

13
223 54
Young Pappy is listed (or ranked) 13 on the list The Best Chicago Rappers
shnigaa added Young Pappy

14
760 406
Mick Jenkins is listed (or ranked) 14 on the list The Best Chicago Rappers
Mick Jenkins

15
757 347
Earl Sweatshirt is listed (or ranked) 15 on the list The Best Chicago Rappers
Earl Sweatshirt Earl, Doris, Chum

The Greatest Rappers of All Time The Social Issues You Care About Most

16
621 300
SZA is listed (or ranked) 16 on the list The Best Chicago Rappers
charlie54 added SZA Z, See.SZA.Run EP, S EP

17
706 359
Lil Reese is listed (or ranked) 17 on the list The Best Chicago Rappers
Lil Reese Supa Savage

18
717 376
Fredo Santana is listed (or ranked) 18 on the list The Best Chicago Rappers
Fredo Santana It's A Scary Site

19
590 339
King Louie is listed (or ranked) 19 on the list The Best Chicago Rappers
King Louie Showtime, My Hoes They Do Drugs, Your Pussy Is My Pillow

20
546 296
Da Brat is listed (or ranked) 20 on the list The Best Chicago Rappers
Da Brat Funkdafied, Unrestricted, Miss P.

21
583 300
Tink is listed (or ranked) 21 on the list The Best Chicago Rappers
Tink

22
471 278
Rhymefest is listed (or ranked) 22 on the list The Best Chicago Rappers
Rhymefest Blue Collar, Mark Ronson Presents Rhymefest: Man in the Mirror, Raw Dawg

23
424 210
Kids These Days is listed (or ranked) 23 on the list The Best Chicago Rappers
Kids These Days Traphouse Rock, All These Interruptions, Manifest Destiny

24
348 165
Do or Die is listed (or ranked) 24 on the list The Best Chicago Rappers
Do or Die Pimpin Ain't Dead, D.O.D., Back 2 the Game

25
412 207
Crucial Conflict is listed (or ranked) 25 on the list The Best Chicago Rappers
Crucial Conflict The Final Tic, Good Side Bad Side, Planet Crucon

26
430 240
Chuck Inglish is listed (or ranked) 26 on the list The Best Chicago Rappers
Chuck Inglish Convertibles, Legs, Easily

27
431 242
Ca$his is listed (or ranked) 27 on the list The Best Chicago Rappers
Ca$his The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

28
398 224
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
396 222
Brandun DeShay is listed (or ranked) 29 on the list The Best Chicago Rappers
Brandun DeShay All Day DeShay: AM, Volume: Three! To Get Ready

Once Iconic Musicians Who Ended Up Slummin' It At The County Fair 20 Hilarious GIFs of Cats Pretending to Be People

30
390 220
Rockie Fresh is listed (or ranked) 30 on the list The Best Chicago Rappers
Rockie Fresh The Otherside Redux, Driving 88, The Otherside

31
357 180
No I.d. is listed (or ranked) 31 on the list The Best Chicago Rappers
No I.d.

32
368 203
Kid Sister is listed (or ranked) 32 on the list The Best Chicago Rappers
Kid Sister Pro Nails Super High Shine EP, Ultraviolet, Control

33
340 200
Chris Ruben is listed (or ranked) 33 on the list The Best Chicago Rappers
Cease Days Ortiz added Chris Ruben Coffee & Vinyls - CHICAGO | Beat Maker | MC | Amateur Photographer | Instagram: CHRISRUBEN_ | 3AM | Booking: djceasedays@gmail.comsoundcloud.com/chris_ruben

34
365 229
Juice is listed (or ranked) 34 on the list The Best Chicago Rappers
Juice Something to Feel, Can We Get Personal?, Juice

35
327 195
Naledge is listed (or ranked) 35 on the list The Best Chicago Rappers
Naledge Chicago Picasso, The Kidz in the Hall Present: Naledge

36
326 215
Co-Still is listed (or ranked) 36 on the list The Best Chicago Rappers
1464133153755 added Co-Still

37
110 38
Noname is listed (or ranked) 37 on the list The Best Chicago Rappers
jasem8 added Noname

38
327 228
Capital D is listed (or ranked) 38 on the list The Best Chicago Rappers
Capital D PolyMath, Insomnia, Return of the Renegade

39
293 192
Legendary Traxter is listed (or ranked) 39 on the list The Best Chicago Rappers

40
291 208
Sir Michael Rocks is listed (or ranked) 40 on the list The Best Chicago Rappers
Sir Michael Rocks

41
270 186
Psalm One is listed (or ranked) 41 on the list The Best Chicago Rappers
Psalm One Bio:Chemistry II: Esters and Essays, The Death of the Frequent Flyer

42
301 236
Ty Money is listed (or ranked) 42 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

43
284 203
Open Mike Eagle is listed (or ranked) 43 on the list The Best Chicago Rappers
Open Mike Eagle Unapologetic Art Rap, Rappers Will Die of Natural Causes, Sir Rockabye

The Best Current Pop Groups/Singers The Best EDM YouTube Channels

44
294 238
Qwazaar is listed (or ranked) 44 on the list The Best Chicago Rappers
Qwazaar Walk Thru Walls

45
89 46
Saba is listed (or ranked) 45 on the list The Best Chicago Rappers
skalemba added Saba

46
273 206
Jeremiah Jae is listed (or ranked) 46 on the list The Best Chicago Rappers
Jeremiah Jae Raw Money Raps, Bad Jokes, New Day^! Rawmoney Shit / Legacy

47
277 237
Diverse is listed (or ranked) 47 on the list The Best Chicago Rappers
Tree One A.M., Wylin Out, Big Game

48
265 229
YP is listed (or ranked) 48 on the list The Best Chicago Rappers
YP

49
272 217
Rastabwoykell is listed (or ranked) 49 on the list The Best Chicago Rappers
RastaBwoyKell added Rastabwoykell

50
155 123
GLC is listed (or ranked) 50 on the list The Best Chicago Rappers
JoshuaThomas1 added GLC Hood Celebrity, Love, Life & Loyalty