Bands/Musicians The Best Chicago Rappers  

Ranker Hip Hop
Originally by
92k votes 10.7k voters 166.8k 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!

list ordered by

1
3,003 1,412
G Herbo is listed (or ranked) 1 on the list The Best Chicago Rappers
-1452106876343 added

2
3,235 1,663
Chief Keef is listed (or ranked) 2 on the list The Best Chicago Rappers
JohnBerthiaume added Finally Rich, Back From the Dead, I Don't Like

3
3,409 1,975
Chance The Rapper is listed (or ranked) 3 on the list The Best Chicago Rappers
Acid Rap, Confident, Songs from Scratch: Paranoia

4
3,122 2,168
Kanye West is listed (or ranked) 4 on the list The Best Chicago Rappers
My Beautiful Dark Twisted Fantasy, Late Registration, The College Dropout

5
2,026 1,232
Lupe Fiasco is listed (or ranked) 5 on the list The Best Chicago Rappers
Food & Liquor, Food & Liquor II: The Great American Rap Album, Part 1

6
1,671 1,002
Twista is listed (or ranked) 6 on the list The Best Chicago Rappers
NicholasDecowski added Adrenaline Rush, Kamikaze, The Day After

7
1,983 1,207
Common is listed (or ranked) 7 on the list The Best Chicago Rappers
Resurrection, Be, Like Water for Chocolate

8
2,220 1,098
Lil Durk is listed (or ranked) 8 on the list The Best Chicago Rappers

9
1,772 687
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
1,751 788
Vic Mensa is listed (or ranked) 10 on the list The Best Chicago Rappers
Jasen Waslien added Innanetape, Straight Up, Down on My Luck

11
1,862 929
Lil Bibby is listed (or ranked) 11 on the list The Best Chicago Rappers
-1452106876343 added

12
1,285 577
Earl Sweatshirt is listed (or ranked) 12 on the list The Best Chicago Rappers
Earl, Doris, Chum

13
1,234 520
SZA is listed (or ranked) 13 on the list The Best Chicago Rappers
charlie54 added Z, See.SZA.Run EP, S EP

14
1,284 664
Fredo Santana is listed (or ranked) 14 on the list The Best Chicago Rappers
It's A Scary Site

15
1,085 635
Mick Jenkins is listed (or ranked) 15 on the list The Best Chicago Rappers
Mick Jenkins

16
1,069 701
L'a Capone is listed (or ranked) 16 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

17
1,124 641
Lil Reese is listed (or ranked) 17 on the list The Best Chicago Rappers
Supa Savage

18
431 167
Saba is listed (or ranked) 18 on the list The Best Chicago Rappers
skalemba added Saba

19
876 449
Tink is listed (or ranked) 19 on the list The Best Chicago Rappers
Tink

20
432 178
Noname is listed (or ranked) 20 on the list The Best Chicago Rappers
jasem8 added Noname

21
848 490
Da Brat is listed (or ranked) 21 on the list The Best Chicago Rappers
Funkdafied, Unrestricted, Miss P.

22
647 327
Young Pappy is listed (or ranked) 22 on the list The Best Chicago Rappers
shnigaa added Young Pappy

23
611 298
No I.d. is listed (or ranked) 23 on the list The Best Chicago Rappers
No I.d.

24
621 303
Do or Die is listed (or ranked) 24 on the list The Best Chicago Rappers
Pimpin Ain't Dead, D.O.D., Back 2 the Game

25
661 329
Crucial Conflict is listed (or ranked) 25 on the list The Best Chicago Rappers
The Final Tic, Good Side Bad Side, Planet Crucon

26
716 463
Rhymefest is listed (or ranked) 26 on the list The Best Chicago Rappers
Blue Collar, Mark Ronson Presents Rhymefest: Man in the Mirror, Raw Dawg

27
613 343
Rockie Fresh is listed (or ranked) 27 on the list The Best Chicago Rappers
The Otherside Redux, Driving 88, The Otherside

28
636 363
Chuck Inglish is listed (or ranked) 28 on the list The Best Chicago Rappers
Convertibles, Legs, Easily

29
642 369
Ca$his is listed (or ranked) 29 on the list The Best Chicago Rappers
The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

30
619 356
Gil Scott-Heron is listed (or ranked) 30 on the list The Best Chicago Rappers
Bridges, Winter in America, The First Minute of a New Day

31
584 333
Brandun DeShay is listed (or ranked) 31 on the list The Best Chicago Rappers
All Day DeShay: AM, Volume: Three! To Get Ready

32
621 324
Kids These Days is listed (or ranked) 32 on the list The Best Chicago Rappers
Traphouse Rock, All These Interruptions, Manifest Destiny

33
501 268
Taylor Bennett is listed (or ranked) 33 on the list The Best Chicago Rappers
Jasen Waslien added Taylor Bennett

34
565 335
Juice is listed (or ranked) 34 on the list The Best Chicago Rappers
Something to Feel, Can We Get Personal?, Juice

35
551 295
Kid Sister is listed (or ranked) 35 on the list The Best Chicago Rappers
Pro Nails Super High Shine EP, Ultraviolet, Control

36
493 285
Sir Michael Rocks is listed (or ranked) 36 on the list The Best Chicago Rappers
Sir Michael Rocks

37
518 300
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
509 301
Co-Still is listed (or ranked) 38 on the list The Best Chicago Rappers
1464133153755 added Co-Still

39
509 272
Naledge is listed (or ranked) 39 on the list The Best Chicago Rappers
Chicago Picasso, The Kidz in the Hall Present: Naledge

40
509 313
Capital D is listed (or ranked) 40 on the list The Best Chicago Rappers
PolyMath, Insomnia, Return of the Renegade

41
441 261
Joey Purp is listed (or ranked) 41 on the list The Best Chicago Rappers
Jasen Waslien added

42
493 272
Open Mike Eagle is listed (or ranked) 42 on the list The Best Chicago Rappers
Unapologetic Art Rap, Rappers Will Die of Natural Causes, Sir Rockabye

43
485 272
Legendary Traxter is listed (or ranked) 43 on the list The Best Chicago Rappers

44
182 56
Mick Jenkins is listed (or ranked) 44 on the list The Best Chicago Rappers

45
457 258
Psalm One is listed (or ranked) 45 on the list The Best Chicago Rappers
Bio:Chemistry II: Esters and Essays, The Death of the Frequent Flyer

46
493 315
Ty Money is listed (or ranked) 46 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

47
770 612
King Louie is listed (or ranked) 47 on the list The Best Chicago Rappers
Showtime, My Hoes They Do Drugs, Your Pussy Is My Pillow

48
347 186
GLC is listed (or ranked) 48 on the list The Best Chicago Rappers
JoshuaThomas1 added Hood Celebrity, Love, Life & Loyalty

49
340 123
Sharkula is listed (or ranked) 49 on the list The Best Chicago Rappers
1519704292721 added Sharkula

50
455 276
Jeremiah Jae is listed (or ranked) 50 on the list The Best Chicago Rappers
Raw Money Raps, Bad Jokes, New Day