Best Singers from Chicago: Top 10 Talented Musicians to Watch Out For

Best Singers from Chicago
Written by Corey Morgan

Chicago is a city that has given birth to many talented musicians, including some of the most iconic singers in the world. From blues legends to modern-day pop stars, the Windy City has produced a diverse range of vocalists who have made a significant impact on the music industry.

One of the most famous singers to come out of Chicago is Sam Cooke, a soulful crooner who rose to fame in the 1950s and 60s. Known for hits like “You Send Me” and “Chain Gang,” Cooke’s smooth, silky voice and heartfelt lyrics made him one of the most beloved singers of his time.

Another legendary Chicago singer is Muddy Waters, a bluesman who helped define the genre with his raw, powerful vocals and electrifying guitar playing.

But Chicago’s musical legacy doesn’t end with these icons. The city has continued to produce talented singers in a variety of genres, from Kanye West and Chance the Rapper in hip-hop to Jennifer Hudson and R. Kelly in R&B.

Whether they’re belting out anthems or crooning ballads, these singers have all left their mark on the world of music and continue to inspire new generations of artists.

Early Chicago Music Scene

Chicago has a rich history in music, and it all started in the early 20th century. The city’s music scene was heavily influenced by African American musicians who migrated from the South, bringing with them the sounds of blues and jazz.

Chicago’s South Side became a hub for blues music, with clubs like the Checkerboard Lounge and Theresa’s Lounge becoming popular spots for both local and traveling musicians.

During the 1930s, Chicago became a center for jazz music, with legendary musicians such as Nat King Cole and Benny Goodman making their mark on the scene.

The city’s thriving music scene also attracted other notable musicians, including Louis Armstrong and Duke Ellington, who performed at venues like the Regal Theater and the Chicago Theater.

Chicago’s music scene continued to evolve in the 1950s and 1960s, with the rise of R&B and soul music. Artists like Curtis Mayfield, Jerry Butler, and The Impressions gained popularity during this time, with many of them starting their careers in Chicago.

Overall, the early Chicago music scene was a melting pot of different sounds and cultures, with African American musicians playing a major role in shaping the city’s musical identity. Today, Chicago continues to be a hub for music, with a diverse range of genres and artists calling the city home.

Top Singers from Chicago

1. Sam Cooke

Sam Cooke, also known as the King of Soul, was born in Clarksdale, Mississippi, but moved to Chicago as a child. He began his career as a gospel singer and later transitioned to secular music.

Cooke’s smooth and soulful voice earned him hits such as “You Send Me” and “A Change Is Gonna Come”. His music continues to inspire and influence singers today.

2. Jennifer Hudson

Hailing from Chicago, Jennifer Hudson is an actress and singer who has won both the Grammy and Academy Awards.

She rose to fame as a contestant on American Idol and later starred in the movie adaptation of the musical Dreamgirls. Hudson’s powerful voice and soulful delivery have earned her hits such as “Spotlight” and “And I Am Telling You I’m Not Going”.

3. R. Kelly

Kelly, a singer-songwriter from Chicago, is a controversial figure. Despite his personal controversies, his music has had a significant impact on the R&B and hip-hop genres. Kelly’s chart-toppers include “I Believe I Can Fly” and “Ignition (Remix)”.

4. Kanye West

Hailing from Chicago, Kanye West is a rapper, producer, and fashion designer.

He has been one of the most influential figures in hip-hop and pop music since the early 2000s. West’s hits include “Gold Digger” and “Stronger”. He has also produced hits for other artists, such as Jay-Z and Beyoncé.

5. Chaka Khan

Chaka Khan, also known as the Queen of Funk, was born and raised in Chicago. She began her career as the lead singer of the funk band Rufus before transitioning to a successful solo career.

Khan’s hits include “I’m Every Woman” and “Ain’t Nobody”. Her powerful voice and energetic stage presence have earned her a place in music history.

Honorable Mentions

6. Mavis Staples

Mavis Staples is a legendary gospel and R&B singer from Chicago. She began her career in the 1950s with her family’s group, The Staple Singers.

Over the years, she has collaborated with artists such as Bob Dylan, Prince, and Wilco. Her powerful voice and socially conscious lyrics have earned her numerous accolades, including a Grammy Lifetime Achievement Award.

7. Curtis Mayfield

Curtis Mayfield was a singer, songwriter, and producer who was a major figure in soul music in the 1960s and 1970s.

He began his career as a member of The Impressions, but later went on to have a successful solo career. He was known for his socially conscious lyrics and his ability to blend soul, funk, and rock into his music.

8. Common

Common, born Lonnie Rashid Lynn Jr., is a rapper, actor, and writer from Chicago. He has released numerous critically acclaimed albums, including “Be” and “Like Water for Chocolate.” He is known for his introspective lyrics and his ability to blend different genres of music into his work.

9. Nat King Cole

Born in Montgomery, Alabama, Nat King Cole was a jazz pianist and vocalist who was raised in Chicago.

He began his career as a jazz pianist, but later became a successful pop and ballad singer. He is best known for his smooth, silky voice and his hits such as “Unforgettable” and “Mona Lisa.”

10. Lupe Fiasco

Lupe Fiasco is a rapper, producer, and entrepreneur from Chicago. He has released several successful albums, including “Food & Liquor” and “The Cool.” He is known for his socially conscious lyrics and his ability to blend different genres of music into his work.

These musicians are just a few of the many talented singers from Chicago. Their contributions to music have helped to shape the city’s rich musical history and have influenced countless artists across the globe.


Chicago has produced some of the most iconic and influential musicians in history. From the early jazz and blues legends like Nat King Cole and Benny Goodman to the rock and roll pioneers like Chicago, the city’s music scene has left an indelible mark on the industry.

Some of the most famous singers to come out of Chicago include Jennifer Hudson, R. Kelly, and Kanye West. Each artist has their unique style and has contributed to the city’s diverse music scene.

It is also worth noting that Chicago has a thriving underground music scene, with many up-and-coming artists making a name for themselves.

The city’s music festivals, such as Lollapalooza and Pitchfork Music Festival, provide a platform for these artists to showcase their talents and reach wider audiences.

Overall, Chicago’s music scene continues to thrive, with new artists emerging and established acts continuing to produce innovative and exciting music. It is a testament to the city’s rich musical heritage and its ongoing commitment to nurturing and supporting new talent.