music The Best Chicago Rappers  

Ranker Hip Hop
Originally by
50.0k votes 5.9k voters 100.1k views 69 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
1,939 927
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 Best Songs About Chicago The Best Indie Folk Bands & Artists

2
1,809 980
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
1,477 693
G Herbo is listed (or ranked) 3 on the list The Best Chicago Rappers
-1452106876343 added G Herbo

4
1,608 841
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
817 300
Montana of 300 is listed (or ranked) 5 on the list The Best Chicago Rappers
PorzinGOD added Montana of 300 Cursed With a Blessing, Gunz n Roses, Fire in the Church

6
1,150 575
Lil Durk is listed (or ranked) 6 on the list The Best Chicago Rappers

7
1,203 657
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
1,141 532
Lil Bibby is listed (or ranked) 8 on the list The Best Chicago Rappers
-1452106876343 added Lil Bibby

9
1,175 640
Common is listed (or ranked) 9 on the list The Best Chicago Rappers
Common Resurrection, Be, Like Water for Chocolate

10
970 424
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
979 536
Twista is listed (or ranked) 11 on the list The Best Chicago Rappers
NicholasDecowski added Twista Adrenaline Rush, Kamikaze, The Day After

12
739 393
Mick Jenkins is listed (or ranked) 12 on the list The Best Chicago Rappers
Mick Jenkins

13
617 341
L'a Capone is listed (or ranked) 13 on the list The Best Chicago Rappers
Zachary Butt added L'a Capone

14
677 345
Lil Reese is listed (or ranked) 14 on the list The Best Chicago Rappers
Lil Reese Supa Savage

15
581 290
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 Dressed Rappers 15 Songs That Don't Mean What You Think They Do

16
692 366
Fredo Santana is listed (or ranked) 16 on the list The Best Chicago Rappers
Fredo Santana It's A Scary Site

17
720 335
Earl Sweatshirt is listed (or ranked) 17 on the list The Best Chicago Rappers
Earl Sweatshirt Earl, Doris, Chum

18
570 292
Tink is listed (or ranked) 18 on the list The Best Chicago Rappers
Tink

19
534 287
Da Brat is listed (or ranked) 19 on the list The Best Chicago Rappers
Da Brat Funkdafied, Unrestricted, Miss P.

20
568 330
King Louie is listed (or ranked) 20 on the list The Best Chicago Rappers
King Louie Showtime, My Hoes They Do Drugs, Your Pussy Is My Pillow

21
466 269
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
184 42
Young Pappy is listed (or ranked) 22 on the list The Best Chicago Rappers
shnigaa added Young Pappy

23
425 232
Chuck Inglish is listed (or ranked) 23 on the list The Best Chicago Rappers
Chuck Inglish Convertibles, Legs, Easily

24
425 235
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
393 214
Brandun DeShay is listed (or ranked) 25 on the list The Best Chicago Rappers
Brandun DeShay All Day DeShay: AM, Volume: Three! To Get Ready

26
394 217
Gil Scott-Heron is listed (or ranked) 26 on the list The Best Chicago Rappers
Gil Scott-Heron Bridges, Winter in America, The First Minute of a New Day

27
387 212
Rockie Fresh is listed (or ranked) 27 on the list The Best Chicago Rappers
Rockie Fresh The Otherside Redux, Driving 88, The Otherside

28
416 202
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
406 199
Crucial Conflict is listed (or ranked) 29 on the list The Best Chicago Rappers
Crucial Conflict The Final Tic, Good Side Bad Side, Planet Crucon

The Greatest Rappers of All Time 31 Things That Are Normal In The Day, But Terrifying At Night

30
339 157
Do or Die is listed (or ranked) 30 on the list The Best Chicago Rappers
Do or Die Pimpin Ain't Dead, D.O.D., Back 2 the Game

31
190 59
Famous Dex is listed (or ranked) 31 on the list The Best Chicago Rappers
Guest_2f236cc2-bbfa-4c5f-a958-66aeb7c27a83 added Famous Dex

32
349 175
No I.d. is listed (or ranked) 32 on the list The Best Chicago Rappers
No I.d.

33
336 194
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
367 192
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
360 222
Juice is listed (or ranked) 35 on the list The Best Chicago Rappers
Juice Something to Feel, Can We Get Personal?, Juice

36
326 206
Co-Still is listed (or ranked) 36 on the list The Best Chicago Rappers
1464133153755 added Co-Still

37
327 219
Capital D is listed (or ranked) 37 on the list The Best Chicago Rappers
Capital D PolyMath, Insomnia, Return of the Renegade

38
324 188
Naledge is listed (or ranked) 38 on the list The Best Chicago Rappers
Naledge Chicago Picasso, The Kidz in the Hall Present: Naledge

39
287 203
Sir Michael Rocks is listed (or ranked) 39 on the list The Best Chicago Rappers
Sir Michael Rocks

40
97 33
Noname is listed (or ranked) 40 on the list The Best Chicago Rappers
jasem8 added Noname

41
289 187
Legendary Traxter is listed (or ranked) 41 on the list The Best Chicago Rappers

42
300 229
Ty Money is listed (or ranked) 42 on the list The Best Chicago Rappers
ReginaldDavis added Ty Money

43
294 230
Qwazaar is listed (or ranked) 43 on the list The Best Chicago Rappers
Qwazaar Walk Thru Walls

The Best Chicago Blues Songs The Grossest Personal Habits

44
267 181
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
277 229
Diverse is listed (or ranked) 45 on the list The Best Chicago Rappers
Tree One A.M., Wylin Out, Big Game

46
278 198
Open Mike Eagle is listed (or ranked) 46 on the list The Best Chicago Rappers
Open Mike Eagle Unapologetic Art Rap, Rappers Will Die of Natural Causes, Sir Rockabye

47
265 221
YP is listed (or ranked) 47 on the list The Best Chicago Rappers
YP

48
272 199
Jeremiah Jae is listed (or ranked) 48 on the list The Best Chicago Rappers
Jeremiah Jae Raw Money Raps, Bad Jokes, New Day^! Rawmoney Shit / Legacy

49
151 118
GLC is listed (or ranked) 49 on the list The Best Chicago Rappers
JoshuaThomas1 added GLC Hood Celebrity, Love^! Life & Loyalty, Welcome to Haterville

50
272 210
Rastabwoykell is listed (or ranked) 50 on the list The Best Chicago Rappers
RastaBwoyKell added Rastabwoykell