The Greatest Chicago Rappers of All Time

What rappers are from Chicago? Let’s find out. From the gritty streets of the Windy City, Chicago’s rap scene has stood out as one of hip-hop’s most potent hotbeds of talent, innovation, and cultural influence.

A metropolis of diverging sounds and stories, Chicago’s rap legacy encompasses the soulful rhythms of Kanye West’s samples, the poignant introspection of Common’s verses, and the drill-infused beats that young lions like Chief Keef brought to the game.

What Rappers Are from Chicago?

This city birthed Saba’s vivid poetic narratives, Lupe Fiasco’s conscious awakening, and the soulful resurgence of artists like Noname.

Whether you are talking about the legacy of pioneers like Twista or the innovative dynamism of Chance the Rapper, Chicago’s rap panorama offers a myriad of styles that reflect its complex urban tapestry.

A city where jazz, blues, and hip-hop intertwine, Chicago has solidified its place as an indomitable force in the rap culture, birthing legends and shaping the very fabric of hip-hop culture.

What Rappers Are from Chicago?

A countdown of the most popular Chicago Rap artists in order of streams on Spotify as lead artists is as follows:

33 Tay Capone

Streams as a lead artist: 4.7M

Streams as a featured artist: 67K

Most streamed song of all time by Tay Capone: Deep in with 809K streams

32 Prince Dre

Streams as a lead artist: 12.1M

Streams as a featured artist: 91.2M

The most streamed song of all time by Prince Dre: Back Again with 90.6M streams

31 Tadoe

Streams as a lead artist: 14.3M

Streams as a featured artist: 20.8M

Most streamed song of all time by Tadoe: Tuxedo with 7.8M streams

30 Rondonumbanine

Streams as a lead artist: 16.1M

Streams as a featured artist: 758K

Most streamed song of all time by Rondonumbanine: Play For Keeps with 6.6M streams

29 Ballout

Streams as a lead artist: 17.8M

Streams as a featured artist: 24.7M

The most streamed song of all time by Ballout: Been Ballin’ with 10.9M streams

28 Booka600

Streams as a lead artist: 38.5M

Streams as a featured artist: 92.5M

Most streamed song of all time by Booka600: JUMP with 30.9M streams

27 Canon

Streams as a lead artist: 45.8M

Most streamed song of all time by Canon: Motivation with 5.6M streams

26 Lil Bibby

Streams as a lead artist: 58.6M

Streams as a featured artist: 101.4M

Most streamed song of all time by Lil Bibby: Kill Shit with 31.7M streams

25 Lil Reese

Streams as a lead artist: 60.6M

Streams as a featured artist: 344.9M

The most streamed song of all time by Lil Reese: I Don’t Like with 315.3M streams

24 Fredo Santana

Streams as a lead artist: 81.0M

Streams as a featured artist: 3.7M

Most streamed song of all time by Fredo Santana: Jealous with 15.7M streams

23 FBG Duck

Streams as a lead artist: 85.8M

Streams as a featured artist: 757K

Most streamed song of all time by FBG Duck: Exposing Me Remix with 18.7M streams

22 Young Pappy

Streams as a lead artist: 96.4M

Streams as a featured artist: 1.2M

Most streamed song of all time by Young Pappy: Killa with 27.5M streams

21 Da Brat

Streams as a lead artist: 107.1M

Streams as a featured artist: 65.7M

Most streamed song of all time by Da Brat: Funkdafied with 30.8M streams

20 Lil Zay Osama

Streams as a lead artist: 127.4M

Streams as a featured artist: 2.5M

Most streamed song of all time by Lil Zay Osama: Changed Up with 21.6M streams

19 BigKayBeezy

Streams as a lead artist: 150.3M

Streams as a featured artist: 2.3M

Most streamed song of all time by BigKayBeezy: BookBag 2.0 with 103.2M streams

18 Lud Foe

Streams as a lead artist: 197.9M

Most streamed song of all time by Lud Foe: In and Out with 25.8M streams

17 Montana of 300

Streams as a lead artist: 247.5M

Most streamed song of all time by Montana of 300: Wifin’ You with 55.3M streams

16 Saba

Streams as a lead artist: 434.9MStreams as a featured artist: 272.8M

Most streamed song of all time by Saba:

Angels with 179.1M streams

15 Noname

Streams as a lead artist: 452.2M

Streams as a featured artist: 100.0M

Most streamed song of all time by Noname: Finish Line / Drown with 74.7M streams

14 Common

Streams as a lead artist: 677.4M

Streams as a featured artist: 536.1M

Most streamed song of all time by Common: Make Her Say with 99.3M streams

13 VIC MENSA

Streams as a lead artist: 693.7M

Streams as a featured artist: 206.2M

Most streamed song of all time by VIC MENSA: Cocoa Butter Kisses with 188.0M streams

12 Calboy

Streams as a lead artist: 742.8M

Streams as a featured artist: 84.2M

Most streamed song of all time by Calboy: Envy Me with 498.3M streams

11 Only The Family

Streams as a lead artist: 804.8M

Streams as a featured artist: 106.8M

Most streamed song of all time by Only The Family: Crazy Story with 284.9M streams

10 Famous Dex

Streams as a lead artist: 1.36B

Streams as a featured artist: 106.2M

Most streamed song of all time by Famous Dex: PICK IT UP with 585.3M streams

9 G Herbo

Streams as a lead artist: 1.43

Streams as a featured artist: 911.0

Most streamed song of all time by G Herbo: PTSD with 411.2M streams

8 Lupe Fiasco

Streams as a lead artist: 1.79B

Streams as a featured artist: 404.5M

Most streamed song of all time by Lupe Fiasco: Battle Scars with 383.9M streams

7 King Von

Streams as a lead artist: 3.02B

Streams as a featured artist: 805.9M

Most streamed song of all time by King Von: Took Her To The O with 547.5M streams

6 Chief Keef

Streams as a lead artist: 3.25B

Streams as a featured artist: 1.21B

Most streamed song of all time by Chief Keef: Love Sosa with 800.8M streams

5 Chance the Rapper

Streams as a lead artist: 3.84B

Streams as a featured artist: 4.39B

Most streamed song of all time by Chance the Rapper: I’m the One with 1.28B streams

4 Lil Durk

Streams as a lead artist: 4.99B

Streams as a featured artist: 7.07B

Most streamed song of all time by Lil Durk: Laugh Now Cry Later with 976.1M streams

3 Polo G

Streams as a lead artist: 8.86B

Streams as a featured artist: 2.61B

Most streamed song of all time by Polo G: RAPSTAR with 960.5M streams

2 Juice WRLD

Streams as a lead artist: 29.53B

Streams as a featured artist: 9.59B

Most streamed song of all time by Juice WRLD: Lucid Dreams with 2.63B streams

1 Kanye West

Streams as a lead artist: 37.41B

Streams as a featured artist: 14.81B

Most streamed song of all time by Kanye West: Ni**as In Paris with 1.50B streams.

Bottom Line

Chicago has an avalanche of good rappers. Some of them have made it to the league of the greatest of all time. The article above exhaustively highlights 33 of the greatest Chicago rappers of all time.

Kindly drop a comment in the section below regarding our selection.

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