bands/musicians The Best Chicago Rappers  

Ranker Hip Hop
Originally by
74.4k votes 8.3k voters 136.2k views 75 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
2,445 1,610
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
2,662 1,518
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
2,250 1,023
G Herbo is listed (or ranked) 3 on the list The Best Chicago Rappers
-1452106876343 added G Herbo

4
1,673 944
Lupe Fiasco is listed (or ranked) 4 on the list The Best Chicago Rappers
Lupe Fiasco Food & Liquor, Food & Liquor II: The Great American Rap Album, Part 1

5
1,632 916
Common is listed (or ranked) 5 on the list The Best Chicago Rappers
Common Resurrection, Be, Like Water for Chocolate

6
2,410 1,259
Chief Keef is listed (or ranked) 6 on the list The Best Chicago Rappers
JohnBerthiaume added Chief Keef Finally Rich, Back From the Dead, I Don't Like

7
1,349 765
Twista is listed (or ranked) 7 on the list The Best Chicago Rappers
NicholasDecowski added Twista Adrenaline Rush, Kamikaze, The Day After

8
1,414 605
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
1,740 900
Lil Durk is listed (or ranked) 9 on the list The Best Chicago Rappers

10
1,344 528
Montana of 300 is listed (or ranked) 10 on the list The Best Chicago Rappers
PorzinGOD added Montana of 300 Cursed With a Blessing, Gunz n Roses, Fire in the Church

11
1,506 773
Lil Bibby is listed (or ranked) 11 on the list The Best Chicago Rappers
-1452106876343 added Lil Bibby

12
1,051 469
Earl Sweatshirt is listed (or ranked) 12 on the list The Best Chicago Rappers
Earl Sweatshirt Earl, Doris, Chum

13
937 405
SZA is listed (or ranked) 13 on the list The Best Chicago Rappers
charlie54 added SZA Z, See.SZA.Run EP, S EP

14
969 520
Mick Jenkins is listed (or ranked) 14 on the list The Best Chicago Rappers
Mick Jenkins

The Best Songs About Chicago

15
872 572
L'a Capone is listed (or ranked) 15 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

16
741 397
Da Brat is listed (or ranked) 16 on the list The Best Chicago Rappers
Da Brat Funkdafied, Unrestricted, Miss P.

17
636 372
Rhymefest is listed (or ranked) 17 on the list The Best Chicago Rappers
Rhymefest Blue Collar, Mark Ronson Presents Rhymefest: Man in the Mirror, Raw Dawg

18
307 100
Noname is listed (or ranked) 18 on the list The Best Chicago Rappers
jasem8 added Noname

19
987 562
Fredo Santana is listed (or ranked) 19 on the list The Best Chicago Rappers
Fredo Santana It's A Scary Site

20
774 384
Tink is listed (or ranked) 20 on the list The Best Chicago Rappers
Tink

21
525 238
Do or Die is listed (or ranked) 21 on the list The Best Chicago Rappers
Do or Die Pimpin Ain't Dead, D.O.D., Back 2 the Game

The Greatest Works of Hunter S. Thompson

22
553 295
Gil Scott-Heron is listed (or ranked) 22 on the list The Best Chicago Rappers
Gil Scott-Heron Bridges, Winter in America, The First Minute of a New Day

23
579 311
Ca$his is listed (or ranked) 23 on the list The Best Chicago Rappers
Ca$his The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

24
523 242
No I.d. is listed (or ranked) 24 on the list The Best Chicago Rappers
No I.d.

25
543 284
Rockie Fresh is listed (or ranked) 25 on the list The Best Chicago Rappers
Rockie Fresh The Otherside Redux, Driving 88, The Otherside

26
576 309
Chuck Inglish is listed (or ranked) 26 on the list The Best Chicago Rappers
Chuck Inglish Convertibles, Legs, Easily

27
578 273
Crucial Conflict is listed (or ranked) 27 on the list The Best Chicago Rappers
Crucial Conflict The Final Tic, Good Side Bad Side, Planet Crucon

28
534 284
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 Greatest White Rappers of All Time

29
568 278
Kids These Days is listed (or ranked) 29 on the list The Best Chicago Rappers
Kids These Days Traphouse Rock, All These Interruptions, Manifest Destiny

30
266 92
Saba is listed (or ranked) 30 on the list The Best Chicago Rappers
skalemba added Saba

31
506 284
Juice is listed (or ranked) 31 on the list The Best Chicago Rappers
Juice Something to Feel, Can We Get Personal?, Juice

32
891 554
Lil Reese is listed (or ranked) 32 on the list The Best Chicago Rappers
Lil Reese Supa Savage

33
473 254
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
507 251
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
462 261
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
438 246
Sir Michael Rocks is listed (or ranked) 36 on the list The Best Chicago Rappers
Sir Michael Rocks

37
464 272
Capital D is listed (or ranked) 37 on the list The Best Chicago Rappers
Capital D PolyMath, Insomnia, Return of the Renegade

38
463 236
Naledge is listed (or ranked) 38 on the list The Best Chicago Rappers
Naledge Chicago Picasso, The Kidz in the Hall Present: Naledge

39
444 253
Young Pappy is listed (or ranked) 39 on the list The Best Chicago Rappers
shnigaa added Young Pappy

40
437 234
Legendary Traxter is listed (or ranked) 40 on the list The Best Chicago Rappers

41
413 222
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
388 231
Taylor Bennett is listed (or ranked) 42 on the list The Best Chicago Rappers
Jasen Waslien added Taylor Bennett

The Best Underground Rappers

43
692 541
King Louie is listed (or ranked) 43 on the list The Best Chicago Rappers
King Louie Showtime, My Hoes They Do Drugs, Your Pussy Is My Pillow

44
435 239
Open Mike Eagle is listed (or ranked) 44 on the list The Best Chicago Rappers
Open Mike Eagle Unapologetic Art Rap, Rappers Will Die of Natural Causes, Sir Rockabye

45
442 277
Ty Money is listed (or ranked) 45 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

46
67 3
Boo & Gotti is listed (or ranked) 46 on the list The Best Chicago Rappers
1519704292721 added Boo & Gotti Perfect Timing

47
300 91
Sharkula is listed (or ranked) 47 on the list The Best Chicago Rappers
1519704292721 added Sharkula

48
300 155
GLC is listed (or ranked) 48 on the list The Best Chicago Rappers
JoshuaThomas1 added GLC Hood Celebrity, Love, Life & Loyalty

49
361 227
Joey Purp is listed (or ranked) 49 on the list The Best Chicago Rappers
Jasen Waslien added Joey Purp

50
66 3
Chali 2na is listed (or ranked) 50 on the list The Best Chicago Rappers
1519704292721 added Chali 2na Fish Market, We Know Something You Don't Know, Lock S**t Down