bands/musicians The Best Chicago Rappers  

Ranker Hip Hop
Originally by
83.3k votes 9.3k voters 148.2k views 80 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!

1
2,675 1,901
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
2,946 1,715
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
2,763 1,417
Chief Keef is listed (or ranked) 3 on the list The Best Chicago Rappers
JohnBerthiaume added Chief Keef Finally Rich, Back From the Dead, I Don't Like

4
2,572 1,190
G Herbo is listed (or ranked) 4 on the list The Best Chicago Rappers
-1452106876343 added G Herbo

5
1,816 1,058
Common is listed (or ranked) 5 on the list The Best Chicago Rappers
Common Resurrection, Be, Like Water for Chocolate

6
1,840 1,085
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
1,506 873
Twista is listed (or ranked) 7 on the list The Best Chicago Rappers
NicholasDecowski added Twista Adrenaline Rush, Kamikaze, The Day After

8
1,933 992
Lil Durk is listed (or ranked) 8 on the list The Best Chicago Rappers

9
1,600 698
Vic Mensa is listed (or ranked) 9 on the list The Best Chicago Rappers
Jasen Waslien added Vic Mensa Innanetape, Straight Up, Down on My Luck

10
1,550 592
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
1,671 869
Lil Bibby is listed (or ranked) 11 on the list The Best Chicago Rappers
-1452106876343 added Lil Bibby

12
1,092 455
SZA is listed (or ranked) 12 on the list The Best Chicago Rappers
charlie54 added SZA Z, See.SZA.Run EP, S EP

13
1,173 519
Earl Sweatshirt is listed (or ranked) 13 on the list The Best Chicago Rappers
Earl Sweatshirt Earl, Doris, Chum

14
1,034 579
Mick Jenkins is listed (or ranked) 14 on the list The Best Chicago Rappers
Mick Jenkins

The Best Songs About Chicago

15
963 652
L'a Capone is listed (or ranked) 15 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

16
1,120 627
Fredo Santana is listed (or ranked) 16 on the list The Best Chicago Rappers
Fredo Santana It's A Scary Site

17
807 443
Da Brat is listed (or ranked) 17 on the list The Best Chicago Rappers
Da Brat Funkdafied, Unrestricted, Miss P.

18
694 421
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
345 117
Saba is listed (or ranked) 19 on the list The Best Chicago Rappers
skalemba added Saba

20
378 141
Noname is listed (or ranked) 20 on the list The Best Chicago Rappers
jasem8 added Noname

21
583 270
No I.d. is listed (or ranked) 21 on the list The Best Chicago Rappers
No I.d.

The Very Best Flavors of Yoplait Yogurt

22
583 269
Do or Die is listed (or ranked) 22 on the list The Best Chicago Rappers
Do or Die Pimpin Ain't Dead, D.O.D., Back 2 the Game

23
632 297
Crucial Conflict is listed (or ranked) 23 on the list The Best Chicago Rappers
Crucial Conflict The Final Tic, Good Side Bad Side, Planet Crucon

24
604 327
Gil Scott-Heron is listed (or ranked) 24 on the list The Best Chicago Rappers
Gil Scott-Heron Bridges, Winter in America, The First Minute of a New Day

25
828 417
Tink is listed (or ranked) 25 on the list The Best Chicago Rappers
Tink

26
595 314
Rockie Fresh is listed (or ranked) 26 on the list The Best Chicago Rappers
Rockie Fresh The Otherside Redux, Driving 88, The Otherside

27
627 341
Ca$his is listed (or ranked) 27 on the list The Best Chicago Rappers
Ca$his The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

28
574 305
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
619 335
Chuck Inglish is listed (or ranked) 29 on the list The Best Chicago Rappers
Chuck Inglish Convertibles, Legs, Easily

30
608 296
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
554 305
Juice is listed (or ranked) 31 on the list The Best Chicago Rappers
Juice Something to Feel, Can We Get Personal?, Juice

32
998 614
Lil Reese is listed (or ranked) 32 on the list The Best Chicago Rappers
Lil Reese Supa Savage

33
509 277
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
541 272
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
477 263
Sir Michael Rocks is listed (or ranked) 35 on the list The Best Chicago Rappers
Sir Michael Rocks

The 37 Greatest On-Stage Falls of All Time

36
497 278
Co-Still is listed (or ranked) 36 on the list The Best Chicago Rappers
1464133153755 added Co-Still

37
457 247
Taylor Bennett is listed (or ranked) 37 on the list The Best Chicago Rappers
Jasen Waslien added Taylor Bennett

38
499 290
Capital D is listed (or ranked) 38 on the list The Best Chicago Rappers
Capital D PolyMath, Insomnia, Return of the Renegade

39
498 253
Naledge is listed (or ranked) 39 on the list The Best Chicago Rappers
Naledge Chicago Picasso, The Kidz in the Hall Present: Naledge

40
521 298
Young Pappy is listed (or ranked) 40 on the list The Best Chicago Rappers
shnigaa added Young Pappy

41
473 252
Legendary Traxter is listed (or ranked) 41 on the list The Best Chicago Rappers

42
449 238
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 Best Underground Rappers

43
481 293
Ty Money is listed (or ranked) 43 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

44
410 244
Joey Purp is listed (or ranked) 44 on the list The Best Chicago Rappers
Jasen Waslien added Joey Purp

45
473 254
Open Mike Eagle is listed (or ranked) 45 on the list The Best Chicago Rappers
Open Mike Eagle Unapologetic Art Rap, Rappers Will Die of Natural Causes, Sir Rockabye

46
336 171
GLC is listed (or ranked) 46 on the list The Best Chicago Rappers
JoshuaThomas1 added GLC Hood Celebrity, Love, Life & Loyalty

47
725 593
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
134 42
Tink is listed (or ranked) 48 on the list The Best Chicago Rappers
Tink

49
452 301
Qwazaar is listed (or ranked) 49 on the list The Best Chicago Rappers
Qwazaar Walk Thru Walls

50
443 293
Diverse is listed (or ranked) 50 on the list The Best Chicago Rappers
Tree One A.M., Wylin Out, Big Game