bands/musicians The Best Chicago Rappers  

Ranker Hip Hop
Originally by
78.8k votes 8.8k voters 142.5k views 76 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
2,566 1,756
Kanye West is listed (or ranked) 1 on the list The Best Chicago Rappers
Kanye West My Beautiful Dark Twisted Fantasy, Late Registration, The College Dropout

2
2,814 1,611
Chance The Rapper is listed (or ranked) 2 on the list The Best Chicago Rappers
Chance The Rapper Acid Rap, Confident, Songs from Scratch: Paranoia

3
2,402 1,108
G Herbo is listed (or ranked) 3 on the list The Best Chicago Rappers
-1452106876343 added G Herbo

4
2,597 1,334
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
1,727 977
Common is listed (or ranked) 5 on the list The Best Chicago Rappers
Common Resurrection, Be, Like Water for Chocolate

6
1,764 1,011
Lupe Fiasco is listed (or ranked) 6 on the list The Best Chicago Rappers
Lupe Fiasco Food & Liquor, Food & Liquor II: The Great American Rap Album, Part 1

7
1,426 817
Twista is listed (or ranked) 7 on the list The Best Chicago Rappers
NicholasDecowski added Twista Adrenaline Rush, Kamikaze, The Day After

8
1,503 647
Vic Mensa is listed (or ranked) 8 on the list The Best Chicago Rappers
Jasen Waslien added Vic Mensa Innanetape, Straight Up, Down on My Luck

9
1,449 554
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
1,824 945
Lil Durk is listed (or ranked) 10 on the list The Best Chicago Rappers

11
1,579 819
Lil Bibby is listed (or ranked) 11 on the list The Best Chicago Rappers
-1452106876343 added Lil Bibby

12
1,127 490
Earl Sweatshirt is listed (or ranked) 12 on the list The Best Chicago Rappers
Earl Sweatshirt Earl, Doris, Chum

13
1,021 433
SZA is listed (or ranked) 13 on the list The Best Chicago Rappers
charlie54 added SZA Z, See.SZA.Run EP, S EP

14
1,003 551
Mick Jenkins is listed (or ranked) 14 on the list The Best Chicago Rappers
Mick Jenkins

The Best Songs About Chicago

15
915 613
L'a Capone is listed (or ranked) 15 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

16
1,056 591
Fredo Santana is listed (or ranked) 16 on the list The Best Chicago Rappers
Fredo Santana It's A Scary Site

17
776 418
Da Brat is listed (or ranked) 17 on the list The Best Chicago Rappers
Da Brat Funkdafied, Unrestricted, Miss P.

18
667 396
Rhymefest is listed (or ranked) 18 on the list The Best Chicago Rappers
Rhymefest Blue Collar, Mark Ronson Presents Rhymefest: Man in the Mirror, Raw Dawg

19
346 121
Noname is listed (or ranked) 19 on the list The Best Chicago Rappers
jasem8 added Noname

20
553 252
No I.d. is listed (or ranked) 20 on the list The Best Chicago Rappers
No I.d.

21
604 322
Ca$his is listed (or ranked) 21 on the list The Best Chicago Rappers
Ca$his The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

The Most Beautiful Women of All Time

22
801 400
Tink is listed (or ranked) 22 on the list The Best Chicago Rappers
Tink

23
579 308
Gil Scott-Heron is listed (or ranked) 23 on the list The Best Chicago Rappers
Gil Scott-Heron Bridges, Winter in America, The First Minute of a New Day

24
571 296
Rockie Fresh is listed (or ranked) 24 on the list The Best Chicago Rappers
Rockie Fresh The Otherside Redux, Driving 88, The Otherside

25
610 284
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
558 255
Do or Die is listed (or ranked) 26 on the list The Best Chicago Rappers
Do or Die Pimpin Ain't Dead, D.O.D., Back 2 the Game

27
602 320
Chuck Inglish is listed (or ranked) 27 on the list The Best Chicago Rappers
Chuck Inglish Convertibles, Legs, Easily

28
557 292
Brandun DeShay is listed (or ranked) 28 on the list The Best Chicago Rappers
Brandun DeShay All Day DeShay: AM, Volume: Three! To Get Ready

The Best Dressed Rappers

29
308 102
Saba is listed (or ranked) 29 on the list The Best Chicago Rappers
skalemba added Saba

30
591 283
Kids These Days is listed (or ranked) 30 on the list The Best Chicago Rappers
Kids These Days Traphouse Rock, All These Interruptions, Manifest Destiny

31
535 292
Juice is listed (or ranked) 31 on the list The Best Chicago Rappers
Juice Something to Feel, Can We Get Personal?, Juice

32
494 261
Chris Ruben is listed (or ranked) 32 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

33
943 584
Lil Reese is listed (or ranked) 33 on the list The Best Chicago Rappers
Lil Reese Supa Savage

34
527 257
Kid Sister is listed (or ranked) 34 on the list The Best Chicago Rappers
Kid Sister Pro Nails Super High Shine EP, Ultraviolet, Control

35
484 266
Co-Still is listed (or ranked) 35 on the list The Best Chicago Rappers
1464133153755 added Co-Still

The Greatest Songs by One-Hit Wonders

36
461 251
Sir Michael Rocks is listed (or ranked) 36 on the list The Best Chicago Rappers
Sir Michael Rocks

37
485 278
Capital D is listed (or ranked) 37 on the list The Best Chicago Rappers
Capital D PolyMath, Insomnia, Return of the Renegade

38
484 241
Naledge is listed (or ranked) 38 on the list The Best Chicago Rappers
Naledge Chicago Picasso, The Kidz in the Hall Present: Naledge

39
422 238
Taylor Bennett is listed (or ranked) 39 on the list The Best Chicago Rappers
Jasen Waslien added Taylor Bennett

40
459 240
Legendary Traxter is listed (or ranked) 40 on the list The Best Chicago Rappers

41
481 275
Young Pappy is listed (or ranked) 41 on the list The Best Chicago Rappers
shnigaa added Young Pappy

42
435 226
Psalm One is listed (or ranked) 42 on the list The Best Chicago Rappers
Psalm One Bio:Chemistry II: Esters and Essays, The Death of the Frequent Flyer

The Greatest Rappers of All Time

43
456 244
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

44
462 282
Ty Money is listed (or ranked) 44 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

45
385 233
Joey Purp is listed (or ranked) 45 on the list The Best Chicago Rappers
Jasen Waslien added Joey Purp

46
322 160
GLC is listed (or ranked) 46 on the list The Best Chicago Rappers
JoshuaThomas1 added GLC Hood Celebrity, Love, Life & Loyalty

47
710 566
King Louie is listed (or ranked) 47 on the list The Best Chicago Rappers
King Louie Showtime, My Hoes They Do Drugs, Your Pussy Is My Pillow

48
321 94
Sharkula is listed (or ranked) 48 on the list The Best Chicago Rappers
1519704292721 added Sharkula

49
432 282
Diverse is listed (or ranked) 49 on the list The Best Chicago Rappers
Tree One A.M., Wylin Out, Big Game

50
438 291
Qwazaar is listed (or ranked) 50 on the list The Best Chicago Rappers
Qwazaar Walk Thru Walls