Bands/Musicians The Best Chicago Rappers  

Ranker Hip Hop
Originally by
86.6k votes 9.8k voters 154.8k views 78 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
2,748 1,278
G Herbo is listed (or ranked) 1 on the list The Best Chicago Rappers
-1452106876343 added G Herbo

2
2,943 1,507
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
3,131 1,827
Chance The Rapper is listed (or ranked) 3 on the list The Best Chicago Rappers
Chance The Rapper Acid Rap, Confident, Songs from Scratch: Paranoia

4
2,854 2,008
Kanye West is listed (or ranked) 4 on the list The Best Chicago Rappers
Kanye West My Beautiful Dark Twisted Fantasy, Late Registration, The College Dropout

5
1,891 1,133
Common is listed (or ranked) 5 on the list The Best Chicago Rappers
Common Resurrection, Be, Like Water for Chocolate

6
1,581 943
Twista is listed (or ranked) 6 on the list The Best Chicago Rappers
NicholasDecowski added Twista Adrenaline Rush, Kamikaze, The Day After

7
1,901 1,162
Lupe Fiasco is listed (or ranked) 7 on the list The Best Chicago Rappers
Lupe Fiasco Food & Liquor, Food & Liquor II: The Great American Rap Album, Part 1

8
1,637 622
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
2,049 1,029
Lil Durk is listed (or ranked) 9 on the list The Best Chicago Rappers

10
1,670 729
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
1,757 889
Lil Bibby is listed (or ranked) 11 on the list The Best Chicago Rappers
-1452106876343 added Lil Bibby

12
1,157 478
SZA is listed (or ranked) 12 on the list The Best Chicago Rappers
charlie54 added SZA Z, See.SZA.Run EP, S EP

13
1,215 543
Earl Sweatshirt is listed (or ranked) 13 on the list The Best Chicago Rappers
Earl Sweatshirt Earl, Doris, Chum

14
1,045 605
Mick Jenkins is listed (or ranked) 14 on the list The Best Chicago Rappers
Mick Jenkins

The Best Songs About Chicago

15
1,182 637
Fredo Santana is listed (or ranked) 15 on the list The Best Chicago Rappers
Fredo Santana It's A Scary Site

16
1,008 669
L'a Capone is listed (or ranked) 16 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

17
848 427
Tink is listed (or ranked) 17 on the list The Best Chicago Rappers
Tink

18
818 469
Da Brat is listed (or ranked) 18 on the list The Best Chicago Rappers
Da Brat Funkdafied, Unrestricted, Miss P.

19
702 440
Rhymefest is listed (or ranked) 19 on the list The Best Chicago Rappers
Rhymefest Blue Collar, Mark Ronson Presents Rhymefest: Man in the Mirror, Raw Dawg

20
371 140
Saba is listed (or ranked) 20 on the list The Best Chicago Rappers
skalemba added Saba

21
594 284
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
590 284
No I.d. is listed (or ranked) 22 on the list The Best Chicago Rappers
No I.d.

23
641 312
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
633 353
Ca$his is listed (or ranked) 24 on the list The Best Chicago Rappers
Ca$his The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

25
1,043 623
Lil Reese is listed (or ranked) 25 on the list The Best Chicago Rappers
Lil Reese Supa Savage

26
600 328
Rockie Fresh is listed (or ranked) 26 on the list The Best Chicago Rappers
Rockie Fresh The Otherside Redux, Driving 88, The Otherside

27
608 341
Gil Scott-Heron is listed (or ranked) 27 on the list The Best Chicago Rappers
Gil Scott-Heron Bridges, Winter in America, The First Minute of a New Day

28
622 347
Chuck Inglish is listed (or ranked) 28 on the list The Best Chicago Rappers
Chuck Inglish Convertibles, Legs, Easily

The Greatest White Rappers of All Time

29
577 318
Brandun DeShay is listed (or ranked) 29 on the list The Best Chicago Rappers
Brandun DeShay All Day DeShay: AM, Volume: Three! To Get Ready

30
387 160
Noname is listed (or ranked) 30 on the list The Best Chicago Rappers
jasem8 added Noname

31
611 309
Kids These Days is listed (or ranked) 31 on the list The Best Chicago Rappers
Kids These Days Traphouse Rock, All These Interruptions, Manifest Destiny

32
556 319
Juice is listed (or ranked) 32 on the list The Best Chicago Rappers
Juice Something to Feel, Can We Get Personal?, Juice

33
566 305
Young Pappy is listed (or ranked) 33 on the list The Best Chicago Rappers
shnigaa added Young Pappy

34
511 285
Chris Ruben is listed (or ranked) 34 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

35
483 269
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
472 255
Taylor Bennett is listed (or ranked) 36 on the list The Best Chicago Rappers
Jasen Waslien added Taylor Bennett

37
543 280
Kid Sister is listed (or ranked) 37 on the list The Best Chicago Rappers
Kid Sister Pro Nails Super High Shine EP, Ultraviolet, Control

38
261 46
Famous Dex is listed (or ranked) 38 on the list The Best Chicago Rappers
1519704292721 added Famous Dex Dexters Laboratory, Dexter the Robot, OhhMannGoddDamm

39
500 286
Co-Still is listed (or ranked) 39 on the list The Best Chicago Rappers
1464133153755 added Co-Still

40
501 298
Capital D is listed (or ranked) 40 on the list The Best Chicago Rappers
Capital D PolyMath, Insomnia, Return of the Renegade

41
500 259
Naledge is listed (or ranked) 41 on the list The Best Chicago Rappers
Naledge Chicago Picasso, The Kidz in the Hall Present: Naledge

42
474 258
Legendary Traxter is listed (or ranked) 42 on the list The Best Chicago Rappers

The Best Underground Rappers

43
421 249
Joey Purp is listed (or ranked) 43 on the list The Best Chicago Rappers
Jasen Waslien added Joey Purp

44
477 259
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
449 244
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
482 300
Ty Money is listed (or ranked) 46 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

47
746 597
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
338 176
GLC is listed (or ranked) 48 on the list The Best Chicago Rappers
JoshuaThomas1 added GLC Hood Celebrity, Love, Life & Loyalty

49
155 45
Mick Jenkins is listed (or ranked) 49 on the list The Best Chicago Rappers

50
453 306
Qwazaar is listed (or ranked) 50 on the list The Best Chicago Rappers
Qwazaar Walk Thru Walls