Bands/Musicians The Best Chicago Rappers  

Ranker Hip Hop
Originally by
96.1k votes 11.3k voters 176k views 81 items

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
3,454 1,781
Chief Keef is listed (or ranked) 1 on the list The Best Chicago Rappers
JohnBerthiaume added Finally Rich, Back From the Dead, I Don't Like

2
3,613 2,078
Chance The Rapper is listed (or ranked) 2 on the list The Best Chicago Rappers
Acid Rap, Confident, Songs from Scratch: Paranoia

3
3,192 1,524
G Herbo is listed (or ranked) 3 on the list The Best Chicago Rappers
-1452106876343 added

4
3,317 2,277
Kanye West is listed (or ranked) 4 on the list The Best Chicago Rappers
My Beautiful Dark Twisted Fantasy, Late Registration, The College Dropout

5
2,099 1,282
Lupe Fiasco is listed (or ranked) 5 on the list The Best Chicago Rappers
Food & Liquor, Food & Liquor II: The Great American Rap Album, Part 1

6
1,727 1,050
Twista is listed (or ranked) 6 on the list The Best Chicago Rappers
NicholasDecowski added Adrenaline Rush, Kamikaze, The Day After

7
2,050 1,253
Common is listed (or ranked) 7 on the list The Best Chicago Rappers
Resurrection, Be, Like Water for Chocolate

8
2,349 1,131
Lil Durk is listed (or ranked) 8 on the list The Best Chicago Rappers

9
1,852 720
Montana of 300 is listed (or ranked) 9 on the list The Best Chicago Rappers
PorzinGOD added Montana of 300 Cursed With a Blessing, Gunz n Roses, Fire in the Church

10
1,804 854
Vic Mensa is listed (or ranked) 10 on the list The Best Chicago Rappers
Jasen Waslien added Innanetape, Straight Up, Down on My Luck

11
1,955 962
Lil Bibby is listed (or ranked) 11 on the list The Best Chicago Rappers
-1452106876343 added

12
1,354 604
Earl Sweatshirt is listed (or ranked) 12 on the list The Best Chicago Rappers
Earl, Doris, Chum

13
1,295 538
SZA is listed (or ranked) 13 on the list The Best Chicago Rappers
charlie54 added Z, See.SZA.Run EP, S EP

14
1,353 689
Fredo Santana is listed (or ranked) 14 on the list The Best Chicago Rappers
It's A Scary Site

15
1,117 662
Mick Jenkins is listed (or ranked) 15 on the list The Best Chicago Rappers
Mick Jenkins

16
1,121 728
L'a Capone is listed (or ranked) 16 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

17
485 189
Saba is listed (or ranked) 17 on the list The Best Chicago Rappers
skalemba added Saba

18
711 351
Young Pappy is listed (or ranked) 18 on the list The Best Chicago Rappers
shnigaa added Young Pappy

19
1,166 671
Lil Reese is listed (or ranked) 19 on the list The Best Chicago Rappers
Supa Savage

20
471 204
Noname is listed (or ranked) 20 on the list The Best Chicago Rappers
jasem8 added Noname

21
899 470
Tink is listed (or ranked) 21 on the list The Best Chicago Rappers
Tink

22
864 513
Da Brat is listed (or ranked) 22 on the list The Best Chicago Rappers
Funkdafied, Unrestricted, Miss P.

23
637 324
Do or Die is listed (or ranked) 23 on the list The Best Chicago Rappers
Pimpin Ain't Dead, D.O.D., Back 2 the Game

24
626 320
No I.d. is listed (or ranked) 24 on the list The Best Chicago Rappers
No I.d.

25
673 350
Crucial Conflict is listed (or ranked) 25 on the list The Best Chicago Rappers
The Final Tic, Good Side Bad Side, Planet Crucon

26
728 482
Rhymefest is listed (or ranked) 26 on the list The Best Chicago Rappers
Blue Collar, Mark Ronson Presents Rhymefest: Man in the Mirror, Raw Dawg

27
528 279
Taylor Bennett is listed (or ranked) 27 on the list The Best Chicago Rappers
Jasen Waslien added Taylor Bennett

28
644 379
Chuck Inglish is listed (or ranked) 28 on the list The Best Chicago Rappers
Convertibles, Legs, Easily

29
629 373
Gil Scott-Heron is listed (or ranked) 29 on the list The Best Chicago Rappers
Bridges, Winter in America, The First Minute of a New Day

30
621 361
Rockie Fresh is listed (or ranked) 30 on the list The Best Chicago Rappers
The Otherside Redux, Driving 88, The Otherside

31
648 385
Ca$his is listed (or ranked) 31 on the list The Best Chicago Rappers
The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

32
590 345
Brandun DeShay is listed (or ranked) 32 on the list The Best Chicago Rappers
All Day DeShay: AM, Volume: Three! To Get Ready

33
629 336
Kids These Days is listed (or ranked) 33 on the list The Best Chicago Rappers
Traphouse Rock, All These Interruptions, Manifest Destiny

34
570 344
Juice is listed (or ranked) 34 on the list The Best Chicago Rappers
Something to Feel, Can We Get Personal?, Juice

35
501 292
Sir Michael Rocks is listed (or ranked) 35 on the list The Best Chicago Rappers
Sir Michael Rocks

36
557 304
Kid Sister is listed (or ranked) 36 on the list The Best Chicago Rappers
Pro Nails Super High Shine EP, Ultraviolet, Control

37
164 19
Ranker Video
1519704292721 added Lud Foe Get Well Foe, No Hooks, No Hooks pt. 2

38
523 308
Chris Ruben is listed (or ranked) 38 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

39
464 268
Joey Purp is listed (or ranked) 39 on the list The Best Chicago Rappers
Jasen Waslien added

40
514 308
Co-Still is listed (or ranked) 40 on the list The Best Chicago Rappers
1464133153755 added Co-Still

41
516 279
Naledge is listed (or ranked) 41 on the list The Best Chicago Rappers
Chicago Picasso, The Kidz in the Hall Present: Naledge

42
201 62
Mick Jenkins is listed (or ranked) 42 on the list The Best Chicago Rappers

43
515 319
Capital D is listed (or ranked) 43 on the list The Best Chicago Rappers
PolyMath, Insomnia, Return of the Renegade

44
506 276
Open Mike Eagle is listed (or ranked) 44 on the list The Best Chicago Rappers
Unapologetic Art Rap, Rappers Will Die of Natural Causes, Sir Rockabye

45
457 261
Famous Dex is listed (or ranked) 45 on the list The Best Chicago Rappers
Anthony Ponzi added Famous Dex

46
491 278
Legendary Traxter is listed (or ranked) 46 on the list The Best Chicago Rappers

47
462 264
Psalm One is listed (or ranked) 47 on the list The Best Chicago Rappers
Bio:Chemistry II: Esters and Essays, The Death of the Frequent Flyer

48
501 319
Ty Money is listed (or ranked) 48 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

49
784 623
King Louie is listed (or ranked) 49 on the list The Best Chicago Rappers
Showtime, My Hoes They Do Drugs, Your Pussy Is My Pillow

50
353 193
GLC is listed (or ranked) 50 on the list The Best Chicago Rappers
JoshuaThomas1 added Hood Celebrity, Love, Life & Loyalty