bands/musicians The Best Chicago Rappers  

Ranker Hip Hop
Originally by
83.5k votes 9.3k voters 148.5k 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
2,686 1,905
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
2,957 1,719
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
2,775 1,421
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
2,584 1,199
G Herbo is listed (or ranked) 4 on the list The Best Chicago Rappers
-1452106876343 added G Herbo

5
1,821 1,066
Common is listed (or ranked) 5 on the list The Best Chicago Rappers
Common Resurrection, Be, Like Water for Chocolate

6
1,844 1,092
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
1,513 879
Twista is listed (or ranked) 7 on the list The Best Chicago Rappers
NicholasDecowski added Twista Adrenaline Rush, Kamikaze, The Day After

8
1,943 996
Lil Durk is listed (or ranked) 8 on the list The Best Chicago Rappers

9
1,602 701
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
1,554 595
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
1,677 870
Lil Bibby is listed (or ranked) 11 on the list The Best Chicago Rappers
-1452106876343 added Lil Bibby

12
1,094 456
SZA is listed (or ranked) 12 on the list The Best Chicago Rappers
charlie54 added SZA Z, See.SZA.Run EP, S EP

13
1,174 520
Earl Sweatshirt is listed (or ranked) 13 on the list The Best Chicago Rappers
Earl Sweatshirt Earl, Doris, Chum

14
1,034 580
Mick Jenkins is listed (or ranked) 14 on the list The Best Chicago Rappers
Mick Jenkins

The Best Songs About Chicago

15
967 654
L'a Capone is listed (or ranked) 15 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

16
1,128 627
Fredo Santana is listed (or ranked) 16 on the list The Best Chicago Rappers
Fredo Santana It's A Scary Site

17
694 422
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
807 448
Da Brat is listed (or ranked) 18 on the list The Best Chicago Rappers
Da Brat Funkdafied, Unrestricted, Miss P.

19
347 119
Saba is listed (or ranked) 19 on the list The Best Chicago Rappers
skalemba added Saba

20
379 143
Noname is listed (or ranked) 20 on the list The Best Chicago Rappers
jasem8 added Noname

21
584 270
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 Very Best Flavors of Yoplait Yogurt

22
583 271
No I.d. is listed (or ranked) 22 on the list The Best Chicago Rappers
No I.d.

23
633 298
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
828 418
Tink is listed (or ranked) 24 on the list The Best Chicago Rappers
Tink

25
604 328
Gil Scott-Heron is listed (or ranked) 25 on the list The Best Chicago Rappers
Gil Scott-Heron Bridges, Winter in America, The First Minute of a New Day

26
595 315
Rockie Fresh is listed (or ranked) 26 on the list The Best Chicago Rappers
Rockie Fresh The Otherside Redux, Driving 88, The Otherside

27
627 342
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
574 306
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
619 336
Chuck Inglish is listed (or ranked) 29 on the list The Best Chicago Rappers
Chuck Inglish Convertibles, Legs, Easily

30
609 297
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
555 306
Juice is listed (or ranked) 31 on the list The Best Chicago Rappers
Juice Something to Feel, Can We Get Personal?, Juice

32
1,002 614
Lil Reese is listed (or ranked) 32 on the list The Best Chicago Rappers
Lil Reese Supa Savage

33
509 278
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
541 273
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
477 264
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
497 280
Co-Still is listed (or ranked) 36 on the list The Best Chicago Rappers
1464133153755 added Co-Still

37
459 249
Taylor Bennett is listed (or ranked) 37 on the list The Best Chicago Rappers
Jasen Waslien added Taylor Bennett

38
499 292
Capital D is listed (or ranked) 38 on the list The Best Chicago Rappers
Capital D PolyMath, Insomnia, Return of the Renegade

39
498 254
Naledge is listed (or ranked) 39 on the list The Best Chicago Rappers
Naledge Chicago Picasso, The Kidz in the Hall Present: Naledge

40
524 299
Young Pappy is listed (or ranked) 40 on the list The Best Chicago Rappers
shnigaa added Young Pappy

41
473 253
Legendary Traxter is listed (or ranked) 41 on the list The Best Chicago Rappers

42
413 245
Joey Purp is listed (or ranked) 42 on the list The Best Chicago Rappers
Jasen Waslien added Joey Purp

The Best Underground Rappers

43
449 239
Psalm One is listed (or ranked) 43 on the list The Best Chicago Rappers
Psalm One Bio:Chemistry II: Esters and Essays, The Death of the Frequent Flyer

44
481 294
Ty Money is listed (or ranked) 44 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

45
473 255
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
727 594
King Louie is listed (or ranked) 46 on the list The Best Chicago Rappers
King Louie Showtime, My Hoes They Do Drugs, Your Pussy Is My Pillow

47
336 172
GLC is listed (or ranked) 47 on the list The Best Chicago Rappers
JoshuaThomas1 added GLC Hood Celebrity, Love, Life & Loyalty

48
134 43
Tink is listed (or ranked) 48 on the list The Best Chicago Rappers
Tink

49
452 302
Qwazaar is listed (or ranked) 49 on the list The Best Chicago Rappers
Qwazaar Walk Thru Walls

50
443 294
Diverse is listed (or ranked) 50 on the list The Best Chicago Rappers
Tree One A.M., Wylin Out, Big Game