Bands/Musicians The Best Chicago Rappers  

Ranker Hip Hop
Originally by
98.6k votes 11.7k voters 181.4k views 82 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
3,574 1,859
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
3,299 1,586
G Herbo is listed (or ranked) 2 on the list The Best Chicago Rappers
-1452106876343 added

3
3,716 2,160
Chance The Rapper is listed (or ranked) 3 on the list The Best Chicago Rappers
Acid Rap, Confident, Songs from Scratch: Paranoia

4
3,431 2,356
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
2,435 1,161
Lil Durk is listed (or ranked) 5 on the list The Best Chicago Rappers

6
2,098 1,298
Common is listed (or ranked) 6 on the list The Best Chicago Rappers
Resurrection, Be, Like Water for Chocolate

7
2,134 1,334
Lupe Fiasco is listed (or ranked) 7 on the list The Best Chicago Rappers
Food & Liquor, Food & Liquor II: The Great American Rap Album, Part 1

8
1,766 1,095
Twista is listed (or ranked) 8 on the list The Best Chicago Rappers
NicholasDecowski added Adrenaline Rush, Kamikaze, The Day After

9
1,913 749
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
2,020 983
Lil Bibby is listed (or ranked) 10 on the list The Best Chicago Rappers
-1452106876343 added

11
1,835 902
Vic Mensa is listed (or ranked) 11 on the list The Best Chicago Rappers
Jasen Waslien added Innanetape, Straight Up, Down on My Luck

12
1,395 634
Earl Sweatshirt is listed (or ranked) 12 on the list The Best Chicago Rappers
Earl, Doris, Chum

13
1,331 559
SZA is listed (or ranked) 13 on the list The Best Chicago Rappers
charlie54 added Z, See.SZA.Run EP, S EP

14
1,405 702
Fredo Santana is listed (or ranked) 14 on the list The Best Chicago Rappers
It's A Scary Site

15
1,161 746
L'a Capone is listed (or ranked) 15 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

16
1,139 684
Mick Jenkins is listed (or ranked) 16 on the list The Best Chicago Rappers
Mick Jenkins

17
755 365
Young Pappy is listed (or ranked) 17 on the list The Best Chicago Rappers
shnigaa added Young Pappy

18
525 211
Saba is listed (or ranked) 18 on the list The Best Chicago Rappers
skalemba added Saba

19
1,202 685
Lil Reese is listed (or ranked) 19 on the list The Best Chicago Rappers
Supa Savage

20
515 225
Noname is listed (or ranked) 20 on the list The Best Chicago Rappers
jasem8 added Noname

21
908 486
Tink is listed (or ranked) 21 on the list The Best Chicago Rappers
Tink

22
880 526
Da Brat is listed (or ranked) 22 on the list The Best Chicago Rappers
Funkdafied, Unrestricted, Miss P.

23
651 337
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
199 24
Ranker Video
johnstonismyname added Lud Foe Get Well Foe, No Hooks, No Hooks pt. 2

25
682 360
Crucial Conflict is listed (or ranked) 25 on the list The Best Chicago Rappers
The Final Tic, Good Side Bad Side, Planet Crucon

26
634 333
No I.d. is listed (or ranked) 26 on the list The Best Chicago Rappers
No I.d.

27
737 492
Rhymefest is listed (or ranked) 27 on the list The Best Chicago Rappers
Blue Collar, Mark Ronson Presents Rhymefest: Man in the Mirror, Raw Dawg

28
539 289
Taylor Bennett is listed (or ranked) 28 on the list The Best Chicago Rappers
Jasen Waslien added Taylor Bennett

29
652 386
Chuck Inglish is listed (or ranked) 29 on the list The Best Chicago Rappers
Convertibles, Legs, Easily

30
635 380
Gil Scott-Heron is listed (or ranked) 30 on the list The Best Chicago Rappers
Bridges, Winter in America, The First Minute of a New Day

31
626 368
Rockie Fresh is listed (or ranked) 31 on the list The Best Chicago Rappers
The Otherside Redux, Driving 88, The Otherside

32
593 352
Brandun DeShay is listed (or ranked) 32 on the list The Best Chicago Rappers
All Day DeShay: AM, Volume: Three! To Get Ready

33
649 393
Ca$his is listed (or ranked) 33 on the list The Best Chicago Rappers
The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

34
630 343
Kids These Days is listed (or ranked) 34 on the list The Best Chicago Rappers
Traphouse Rock, All These Interruptions, Manifest Destiny

35
574 350
Juice is listed (or ranked) 35 on the list The Best Chicago Rappers
Something to Feel, Can We Get Personal?, Juice

36
213 66
Mick Jenkins is listed (or ranked) 36 on the list The Best Chicago Rappers

37
505 297
Sir Michael Rocks is listed (or ranked) 37 on the list The Best Chicago Rappers
Sir Michael Rocks

38
472 273
Joey Purp is listed (or ranked) 38 on the list The Best Chicago Rappers
Jasen Waslien added

39
489 272
Famous Dex is listed (or ranked) 39 on the list The Best Chicago Rappers
Anthony Ponzi added Famous Dex

40
558 310
Kid Sister is listed (or ranked) 40 on the list The Best Chicago Rappers
Pro Nails Super High Shine EP, Ultraviolet, Control

41
524 312
Chris Ruben is listed (or ranked) 41 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

42
515 313
Co-Still is listed (or ranked) 42 on the list The Best Chicago Rappers
thesinbadwicked added Co-Still

43
518 284
Naledge is listed (or ranked) 43 on the list The Best Chicago Rappers
Chicago Picasso, The Kidz in the Hall Present: Naledge

44
517 324
Capital D is listed (or ranked) 44 on the list The Best Chicago Rappers
PolyMath, Insomnia, Return of the Renegade

45
511 279
Open Mike Eagle is listed (or ranked) 45 on the list The Best Chicago Rappers
Unapologetic Art Rap, Rappers Will Die of Natural Causes, Sir Rockabye

46
492 282
Legendary Traxter is listed (or ranked) 46 on the list The Best Chicago Rappers

47
797 626
King Louie is listed (or ranked) 47 on the list The Best Chicago Rappers
Showtime, My Hoes They Do Drugs, Your Pussy Is My Pillow

48
465 268
Psalm One is listed (or ranked) 48 on the list The Best Chicago Rappers
Bio:Chemistry II: Esters and Essays, The Death of the Frequent Flyer

49
503 324
Ty Money is listed (or ranked) 49 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

50
357 196
GLC is listed (or ranked) 50 on the list The Best Chicago Rappers
JoshuaThomas1 added Hood Celebrity, Love, Life & Loyalty