Bands/Musicians The Best Chicago Rappers  

Ranker Hip Hop
Originally by
90.2k votes 10.4k voters 163.2k 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
3,315 1,928
Chance The Rapper is listed (or ranked) 1 on the list The Best Chicago Rappers
Chance The Rapper Acid Rap, Confident, Songs from Scratch: Paranoia

2
3,138 1,615
Chief Keef is listed (or ranked) 2 on the list The Best Chicago Rappers
JohnBerthiaume added Chief Keef Finally Rich, Back From the Dead, I Don't Like

3
3,033 2,117
Kanye West is listed (or ranked) 3 on the list The Best Chicago Rappers
Kanye West My Beautiful Dark Twisted Fantasy, Late Registration, The College Dropout

4
2,916 1,372
G Herbo is listed (or ranked) 4 on the list The Best Chicago Rappers
-1452106876343 added G Herbo

5
1,989 1,206
Lupe Fiasco is listed (or ranked) 5 on the list The Best Chicago Rappers
Lupe Fiasco Food & Liquor, Food & Liquor II: The Great American Rap Album, Part 1

6
1,641 984
Twista is listed (or ranked) 6 on the list The Best Chicago Rappers
NicholasDecowski added Twista Adrenaline Rush, Kamikaze, The Day After

7
2,165 1,078
Lil Durk is listed (or ranked) 7 on the list The Best Chicago Rappers

8
1,734 663
Montana of 300 is listed (or ranked) 8 on the list The Best Chicago Rappers
PorzinGOD added Montana of 300 Cursed With a Blessing, Gunz n Roses, Fire in the Church

9
1,951 1,186
Common is listed (or ranked) 9 on the list The Best Chicago Rappers
Common Resurrection, Be, Like Water for Chocolate

10
1,722 759
Vic Mensa is listed (or ranked) 10 on the list The Best Chicago Rappers
Jasen Waslien added Vic Mensa Innanetape, Straight Up, Down on My Luck

11
1,826 914
Lil Bibby is listed (or ranked) 11 on the list The Best Chicago Rappers
-1452106876343 added Lil Bibby

12
1,202 507
SZA is listed (or ranked) 12 on the list The Best Chicago Rappers
charlie54 added SZA Z, See.SZA.Run EP, S EP

13
1,252 568
Earl Sweatshirt is listed (or ranked) 13 on the list The Best Chicago Rappers
Earl Sweatshirt Earl, Doris, Chum

14
1,254 657
Fredo Santana is listed (or ranked) 14 on the list The Best Chicago Rappers
Fredo Santana It's A Scary Site

15
1,072 624
Mick Jenkins is listed (or ranked) 15 on the list The Best Chicago Rappers
Mick Jenkins

16
1,049 691
L'a Capone is listed (or ranked) 16 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

17
414 157
Saba is listed (or ranked) 17 on the list The Best Chicago Rappers
skalemba added Saba

18
1,094 635
Lil Reese is listed (or ranked) 18 on the list The Best Chicago Rappers
Lil Reese Supa Savage

19
417 169
Noname is listed (or ranked) 19 on the list The Best Chicago Rappers
jasem8 added Noname

20
865 444
Tink is listed (or ranked) 20 on the list The Best Chicago Rappers
Tink

21
836 485
Da Brat is listed (or ranked) 21 on the list The Best Chicago Rappers
Da Brat Funkdafied, Unrestricted, Miss P.

22
610 295
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
601 292
No I.d. is listed (or ranked) 23 on the list The Best Chicago Rappers
No I.d.

24
654 323
Crucial Conflict is listed (or ranked) 24 on the list The Best Chicago Rappers
Crucial Conflict The Final Tic, Good Side Bad Side, Planet Crucon

25
709 456
Rhymefest is listed (or ranked) 25 on the list The Best Chicago Rappers
Rhymefest Blue Collar, Mark Ronson Presents Rhymefest: Man in the Mirror, Raw Dawg

26
623 317
Young Pappy is listed (or ranked) 26 on the list The Best Chicago Rappers
shnigaa added Young Pappy

27
633 355
Chuck Inglish is listed (or ranked) 27 on the list The Best Chicago Rappers
Chuck Inglish Convertibles, Legs, Easily

28
608 336
Rockie Fresh is listed (or ranked) 28 on the list The Best Chicago Rappers
Rockie Fresh The Otherside Redux, Driving 88, The Otherside

29
639 363
Ca$his is listed (or ranked) 29 on the list The Best Chicago Rappers
Ca$his The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

30
616 350
Gil Scott-Heron is listed (or ranked) 30 on the list The Best Chicago Rappers
Gil Scott-Heron Bridges, Winter in America, The First Minute of a New Day

31
582 326
Brandun DeShay is listed (or ranked) 31 on the list The Best Chicago Rappers
Brandun DeShay All Day DeShay: AM, Volume: Three! To Get Ready

32
312 60
Famous Dex is listed (or ranked) 32 on the list The Best Chicago Rappers
1519704292721 added Famous Dex Dexters Laboratory, Dexter the Robot, OhhMannGoddDamm

33
618 318
Kids These Days is listed (or ranked) 33 on the list The Best Chicago Rappers
Kids These Days Traphouse Rock, All These Interruptions, Manifest Destiny

34
490 262
Taylor Bennett is listed (or ranked) 34 on the list The Best Chicago Rappers
Jasen Waslien added Taylor Bennett

35
562 329
Juice is listed (or ranked) 35 on the list The Best Chicago Rappers
Juice Something to Feel, Can We Get Personal?, Juice

36
491 278
Sir Michael Rocks is listed (or ranked) 36 on the list The Best Chicago Rappers
Sir Michael Rocks

37
516 294
Chris Ruben is listed (or ranked) 37 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

38
548 289
Kid Sister is listed (or ranked) 38 on the list The Best Chicago Rappers
Kid Sister Pro Nails Super High Shine EP, Ultraviolet, Control

39
506 295
Co-Still is listed (or ranked) 39 on the list The Best Chicago Rappers
1464133153755 added Co-Still

40
506 307
Capital D is listed (or ranked) 40 on the list The Best Chicago Rappers
Capital D PolyMath, Insomnia, Return of the Renegade

41
505 267
Naledge is listed (or ranked) 41 on the list The Best Chicago Rappers
Naledge Chicago Picasso, The Kidz in the Hall Present: Naledge

42
433 256
Joey Purp is listed (or ranked) 42 on the list The Best Chicago Rappers
Jasen Waslien added Joey Purp

43
482 267
Legendary Traxter is listed (or ranked) 43 on the list The Best Chicago Rappers

44
487 267
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
455 252
Psalm One is listed (or ranked) 45 on the list The Best Chicago Rappers
Psalm One Bio:Chemistry II: Esters and Essays, The Death of the Frequent Flyer

46
491 308
Ty Money is listed (or ranked) 46 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

47
172 51
Mick Jenkins is listed (or ranked) 47 on the list The Best Chicago Rappers

48
764 606
King Louie is listed (or ranked) 48 on the list The Best Chicago Rappers
King Louie Showtime, My Hoes They Do Drugs, Your Pussy Is My Pillow

49
343 182
GLC is listed (or ranked) 49 on the list The Best Chicago Rappers
JoshuaThomas1 added GLC Hood Celebrity, Love, Life & Loyalty

50
108 9
Ranker Video
1519704292721 added Lud Foe Get Well Foe, No Hooks, No Hooks pt. 2