music The Best Chicago Rappers  

Ranker Hip Hop
Originally by
46.0k votes 5.2k voters 89.0k views 68 items Embed

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
1,759 769
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

The Greatest White Rappers of All Time The Best Ford Trucks of All Time

2
1,604 865
Kanye West is listed (or ranked) 2 on the list The Best Chicago Rappers
Kanye West My Beautiful Dark Twisted Fantasy, Late Registration, The College Dropout

3
1,273 618
G Herbo is listed (or ranked) 3 on the list The Best Chicago Rappers
-1452106876343 added G Herbo

4
1,425 761
Chief Keef is listed (or ranked) 4 on the list The Best Chicago Rappers
JohnBerthiaume added Chief Keef Finally Rich, Back From the Dead, I Don't Like

5
1,117 592
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
1,095 583
Common is listed (or ranked) 6 on the list The Best Chicago Rappers
Common Resurrection, Be, Like Water for Chocolate

7
685 246
Montana of 300 is listed (or ranked) 7 on the list The Best Chicago Rappers
PorzinGOD added Montana of 300 Cursed With a Blessing, Gunz n Roses, Fire in the Church

8
1,019 476
Lil Bibby is listed (or ranked) 8 on the list The Best Chicago Rappers
-1452106876343 added Lil Bibby

9
915 489
Twista is listed (or ranked) 9 on the list The Best Chicago Rappers
NicholasDecowski added Twista Adrenaline Rush, Kamikaze, The Day After

10
877 380
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
1,021 531
Lil Durk is listed (or ranked) 11 on the list The Best Chicago Rappers

12
712 354
Mick Jenkins is listed (or ranked) 12 on the list The Best Chicago Rappers
Mick Jenkins

13
668 298
Earl Sweatshirt is listed (or ranked) 13 on the list The Best Chicago Rappers
Earl Sweatshirt Earl, Doris, Chum

14
539 259
Tink is listed (or ranked) 14 on the list The Best Chicago Rappers
Tink

15
521 252
SZA is listed (or ranked) 15 on the list The Best Chicago Rappers
charlie54 added SZA Z, See.SZA.Run EP, S EP

The Best Songs About Chicago 16 Songs That Don't Mean What You Think They Do

16
652 339
Fredo Santana is listed (or ranked) 16 on the list The Best Chicago Rappers
Fredo Santana It's A Scary Site

17
627 320
Lil Reese is listed (or ranked) 17 on the list The Best Chicago Rappers
Lil Reese Supa Savage

18
543 314
L'a Capone is listed (or ranked) 18 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

19
513 259
Da Brat is listed (or ranked) 19 on the list The Best Chicago Rappers
Da Brat Funkdafied, Unrestricted, Miss P.

20
388 183
Crucial Conflict is listed (or ranked) 20 on the list The Best Chicago Rappers
Jay Clayton added Crucial Conflict The Final Tic, Good Side Bad Side, Planet Crucon

21
455 244
Rhymefest is listed (or ranked) 21 on the list The Best Chicago Rappers
Rhymefest Blue Collar, Mark Ronson Presents Rhymefest: Man in the Mirror, Raw Dawg

22
540 299
King Louie is listed (or ranked) 22 on the list The Best Chicago Rappers
King Louie Showtime, My Hoes They Do Drugs, Your Pussy Is My Pillow

23
416 217
Ca$his is listed (or ranked) 23 on the list The Best Chicago Rappers
Ca$his The County Hound EP, Six-Point Stars & Cocked Hats, The Art of Dying

24
415 216
Chuck Inglish is listed (or ranked) 24 on the list The Best Chicago Rappers
Chuck Inglish Convertibles, Legs, Easily

25
385 200
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
383 198
Brandun DeShay is listed (or ranked) 26 on the list The Best Chicago Rappers
Brandun DeShay All Day DeShay: AM, Volume: Three! To Get Ready

27
377 195
Rockie Fresh is listed (or ranked) 27 on the list The Best Chicago Rappers
Rockie Fresh The Otherside Redux, Driving 88, The Otherside

28
407 186
Kids These Days is listed (or ranked) 28 on the list The Best Chicago Rappers
Kids These Days Traphouse Rock, All These Interruptions, Manifest Destiny

29
317 142
Do or Die is listed (or ranked) 29 on the list The Best Chicago Rappers
Do or Die Pimpin Ain't Dead, D.O.D., Back 2 the Game

The Greatest Rappers of All Time Girls Reveal What They Actually Want for Valentine's Day

30
358 201
Juice is listed (or ranked) 30 on the list The Best Chicago Rappers
Juice Something to Feel, Can We Get Personal?, Juice

31
336 158
No I.d. is listed (or ranked) 31 on the list The Best Chicago Rappers
No I.d.

32
362 175
Kid Sister is listed (or ranked) 32 on the list The Best Chicago Rappers
Kid Sister Pro Nails Super High Shine EP, Ultraviolet, Control

33
328 177
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
325 186
Co-Still is listed (or ranked) 34 on the list The Best Chicago Rappers
1464133153755 added Co-Still

35
119 25
Young Pappy is listed (or ranked) 35 on the list The Best Chicago Rappers
shnigaa added Young Pappy

36
327 201
Capital D is listed (or ranked) 36 on the list The Best Chicago Rappers
Capital D PolyMath, Insomnia, Return of the Renegade

37
132 38
Famous Dex is listed (or ranked) 37 on the list The Best Chicago Rappers
Guest_2f236cc2-bbfa-4c5f-a958-66aeb7c27a83 added Famous Dex

38
316 175
Naledge is listed (or ranked) 38 on the list The Best Chicago Rappers
Naledge Chicago Picasso, The Kidz in the Hall Present: Naledge

39
276 192
Sir Michael Rocks is listed (or ranked) 39 on the list The Best Chicago Rappers
Sir Michael Rocks

40
298 211
Ty Money is listed (or ranked) 40 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

41
293 212
Qwazaar is listed (or ranked) 41 on the list The Best Chicago Rappers
Qwazaar Walk Thru Walls

42
280 175
Legendary Traxter is listed (or ranked) 42 on the list The Best Chicago Rappers

43
277 211
Diverse is listed (or ranked) 43 on the list The Best Chicago Rappers
Tree One A.M., Wylin Out, Big Game

The Best Chicago Blues Songs Political Issues That Matter the Most Right Now

44
259 170
Psalm One is listed (or ranked) 44 on the list The Best Chicago Rappers
Psalm One Bio:Chemistry II: Esters and Essays, The Death of the Frequent Flyer

45
264 204
YP is listed (or ranked) 45 on the list The Best Chicago Rappers
YP

46
73 22
Noname is listed (or ranked) 46 on the list The Best Chicago Rappers
jasem8 added Noname

47
272 193
Rastabwoykell is listed (or ranked) 47 on the list The Best Chicago Rappers
RastaBwoyKell added Rastabwoykell

48
266 189
Open Mike Eagle is listed (or ranked) 48 on the list The Best Chicago Rappers
Open Mike Eagle Unapologetic Art Rap, Rappers Will Die of Natural Causes, Sir Rockabye

49
265 190
Jeremiah Jae is listed (or ranked) 49 on the list The Best Chicago Rappers
Jeremiah Jae Raw Money Raps, Bad Jokes, New Day^! Rawmoney Shit / Legacy

50
241 198
Project Mayhem is listed (or ranked) 50 on the list The Best Chicago Rappers
Project Mayhem