Bands/Musicians The Best Chicago Rappers  

Ranker Hip Hop
Originally by
94.7k votes 11k voters 171.9k 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
3,367 1,728
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
3,536 2,032
Chance The Rapper is listed (or ranked) 2 on the list The Best Chicago Rappers
Acid Rap, Confident, Songs from Scratch: Paranoia

3
3,126 1,484
G Herbo is listed (or ranked) 3 on the list The Best Chicago Rappers
-1452106876343 added

4
3,239 2,239
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
2,078 1,262
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
2,026 1,234
Common is listed (or ranked) 6 on the list The Best Chicago Rappers
Resurrection, Be, Like Water for Chocolate

7
1,700 1,037
Twista is listed (or ranked) 7 on the list The Best Chicago Rappers
NicholasDecowski added Adrenaline Rush, Kamikaze, The Day After

8
2,299 1,120
Lil Durk is listed (or ranked) 8 on the list The Best Chicago Rappers

9
1,819 710
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
1,789 831
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
1,922 951
Lil Bibby is listed (or ranked) 11 on the list The Best Chicago Rappers
-1452106876343 added

12
1,330 596
Earl Sweatshirt is listed (or ranked) 12 on the list The Best Chicago Rappers
Earl, Doris, Chum

13
1,274 532
SZA is listed (or ranked) 13 on the list The Best Chicago Rappers
charlie54 added Z, See.SZA.Run EP, S EP

14
1,326 680
Fredo Santana is listed (or ranked) 14 on the list The Best Chicago Rappers
It's A Scary Site

15
1,110 654
Mick Jenkins is listed (or ranked) 15 on the list The Best Chicago Rappers
Mick Jenkins

16
1,100 721
L'a Capone is listed (or ranked) 16 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

17
465 179
Saba is listed (or ranked) 17 on the list The Best Chicago Rappers
skalemba added Saba

18
1,157 661
Lil Reese is listed (or ranked) 18 on the list The Best Chicago Rappers
Supa Savage

19
681 344
Young Pappy is listed (or ranked) 19 on the list The Best Chicago Rappers
shnigaa added Young Pappy

20
459 196
Noname is listed (or ranked) 20 on the list The Best Chicago Rappers
jasem8 added Noname

21
891 465
Tink is listed (or ranked) 21 on the list The Best Chicago Rappers
Tink

22
858 505
Da Brat is listed (or ranked) 22 on the list The Best Chicago Rappers
Funkdafied, Unrestricted, Miss P.

23
623 313
No I.d. is listed (or ranked) 23 on the list The Best Chicago Rappers
No I.d.

24
631 318
Do or Die is listed (or ranked) 24 on the list The Best Chicago Rappers
Pimpin Ain't Dead, D.O.D., Back 2 the Game

25
669 345
Crucial Conflict is listed (or ranked) 25 on the list The Best Chicago Rappers
The Final Tic, Good Side Bad Side, Planet Crucon

26
725 477
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
621 356
Rockie Fresh is listed (or ranked) 27 on the list The Best Chicago Rappers
The Otherside Redux, Driving 88, The Otherside

28
628 368
Gil Scott-Heron is listed (or ranked) 28 on the list The Best Chicago Rappers
Bridges, Winter in America, The First Minute of a New Day

29
642 375
Chuck Inglish is listed (or ranked) 29 on the list The Best Chicago Rappers
Convertibles, Legs, Easily

30
648 381
Ca$his is listed (or ranked) 30 on the list The Best Chicago Rappers
The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

31
522 277
Taylor Bennett is listed (or ranked) 31 on the list The Best Chicago Rappers
Jasen Waslien added Taylor Bennett

32
589 343
Brandun DeShay is listed (or ranked) 32 on the list The Best Chicago Rappers
All Day DeShay: AM, Volume: Three! To Get Ready

33
628 334
Kids These Days is listed (or ranked) 33 on the list The Best Chicago Rappers
Traphouse Rock, All These Interruptions, Manifest Destiny

34
570 342
Juice is listed (or ranked) 34 on the list The Best Chicago Rappers
Something to Feel, Can We Get Personal?, Juice

35
501 290
Sir Michael Rocks is listed (or ranked) 35 on the list The Best Chicago Rappers
Sir Michael Rocks

36
557 302
Kid Sister is listed (or ranked) 36 on the list The Best Chicago Rappers
Pro Nails Super High Shine EP, Ultraviolet, Control

37
523 306
Chris Ruben is listed (or ranked) 37 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

38
514 306
Co-Still is listed (or ranked) 38 on the list The Best Chicago Rappers
1464133153755 added Co-Still

39
514 277
Naledge is listed (or ranked) 39 on the list The Best Chicago Rappers
Chicago Picasso, The Kidz in the Hall Present: Naledge

40
514 318
Capital D is listed (or ranked) 40 on the list The Best Chicago Rappers
PolyMath, Insomnia, Return of the Renegade

41
197 61
Mick Jenkins is listed (or ranked) 41 on the list The Best Chicago Rappers

42
457 268
Joey Purp is listed (or ranked) 42 on the list The Best Chicago Rappers
Jasen Waslien added

43
504 275
Open Mike Eagle is listed (or ranked) 43 on the list The Best Chicago Rappers
Unapologetic Art Rap, Rappers Will Die of Natural Causes, Sir Rockabye

44
491 277
Legendary Traxter is listed (or ranked) 44 on the list The Best Chicago Rappers

45
462 262
Psalm One is listed (or ranked) 45 on the list The Best Chicago Rappers
Bio:Chemistry II: Esters and Essays, The Death of the Frequent Flyer

46
500 318
Ty Money is listed (or ranked) 46 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

47
430 256
Famous Dex is listed (or ranked) 47 on the list The Best Chicago Rappers
Anthony Ponzi added Famous Dex

48
144 18
Ranker Video
1519704292721 added Lud Foe Get Well Foe, No Hooks, No Hooks pt. 2

49
780 621
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
353 192
GLC is listed (or ranked) 50 on the list The Best Chicago Rappers
JoshuaThomas1 added Hood Celebrity, Love, Life & Loyalty