Best 22 Rapper from Chicago USA of all time

Twista is a legend among rappers from Chicago. It is the stage name of the renowned American rapper Carl Terrell Mitchell. 

The rapper released his first album under the name Tung Twista in the year 1992. The album was called Runnin' Off at da Mouth. Similarly, the rapper's second album named Resurrection was released in 1994 inside the city of Chicago. 

Mitchell has collaborated with The Legendary Traxster and Cwal's Do or Die in the project Po Pimp. Similarly, in 1998 he collaborated with Chicago area rappers and formed the Speedknot Mobstaz.

The rapper partnered with popular artists including Kanye West and Ludacris to record the album named Kamikaze. 

Taylor Bennett is one of the beloved Chicago rappers on this list. Bennett has been in the music industry since the year 2013. 

Bennett's full name is Taylor Matthew Bennett. Born in the year 1996, Bennett's father used to work for the Mayor of Chicago and made sure that his son pursued his dream of being a singer while continuing formal education. 

The 27-year-old has a unique style of rapping. In addition, the way he presents his music is influential and inspiring at the same time. Bennett released a mixtape named Broad Shoulders in the year 2015.

Similarly, the artist released a single called Rock n Roll, including a video from his Ep named Be Yourself. Bennett is also well-regarded because of his music's eclectic mix of styles.

Lil Durk is a widely renowned American singer and rapper. Druk's real name is Durk Derrick Banks. 

Durk began his musical journey in 2011. Growing up in a financially weak household, the rapper had to endure many hardships during his childhood and young age. 

After releasing the two singles named Sneak Dissin and I'ma Hitta, the rapper thought of taking rap as a full-time career. He received a lot of positive feedback from his listeners and thus decided to give music a chance.

In 2012, the rapper released a mixtape called Life Ain't Joke, which rose his popularity to a great extent. Similarly, his mixtape series, Signed to the Streets, released in 2013, added to his popularity in the music industry.

Open Mike Eagle is the stage name of Michael W. Eagle II. This Chicago rapper is known for his conscious bars. 

Mike Eagle spent most of his childhood in Robert Taylor Homes with his grandparents. He was interested in music and used rap as a hobby. However, when he discovered Dumbfoundead, he developed a deep understanding of music. 

In 2010, Eagle released his first-ever solo album entitled Unapologetic Art Rap. The album also featured some other artists like Busdriver and Nocando.

Open Mike Eagle also collaborated with Dumboundead and Psychosoz to form a trio band called Thirsty Fish. The band's first album, Testing the Waters, became popular in the music industry.

Chance The Rapper is a Chicago Hip Hop artist. The rapper has been in the music industry since the year 2011.

The original name of the rapper is Chancelor Johnathan Bennett. The rapper was born to Ken Williams, an aide to the mayor of Chicago. Therefore, Bennett grew up in a good environment.

The 29-year-old started rapping in the sixth grade. His career officially began in 2011. Bennett was successful in recording his first-ever full-length project within a time period of the span of eight months which included a mixtape named 10 Day. 

The rapper's second mix tape was released in 2013. It was entitled Acid Rap and got downloaded more than 1.5 million times. In 2014, Bennett was presented with the Outstanding Youth Of the Year Award by Rahm Emanuel. Similarly, he was included on the Forbes 30 under 30 in January 2015. 

Vic Mensa is the most controversial among all rappers from Chicago. He is best known for his incendiary views and genre bending music.

Born in 1993, the rapper was born to a white American mother and father from Ghana. Mensa spent his childhood in Hyde Park. The rapper began his career after forming the band called Kids These Days.

The rapper's first studio album was entitled The Autobiography. It was officially released in June 2014.

The Chicago native also founded a punk rock and rap band, 93Punx. The band released a cover of the song Zombie, which became popular among the listeners. At the same time, the band also released their debut single, Camp America.

Common is one of the best ol school Chicago rappers. His original name is Lonnie Rashid Lynn. 

Common began his career in the music industry during the late 1980s. Raised by a single mother, the rapper has a degree in Business Administration. Besides music, he was good in academics too. 

The debut album of the Chicago native entitled Can I Borrow a Dollar? was brought among the listeners in 1992. The album was able to gain immense success.

The rapper's prominence rose even higher after he released Resurrection in 1994. Besides music, Common also has an involvement in the acting industry.

Born with the name Ke'Asha McClureas in Chicago, Queen Key is a popular rapper. She is best known for her performance in songs like Hit A Lix and Take Money.

Queen Key often makes headlines because of her hardcore lyrics. At the same time, the hip-hop world also regards her as one of the unique rappers.

Queen Key started rapping at an early age. She was introduced to the world of music at the age of six. Her projects, including Your Highness and Beauty In A Beast, were released officially in 2016.

According to Key, she is highly inspired by artists such as Lil Kim, Trina, and Lil Wayne. In addition, she also adores the work my Nicki Minaj. A mom of three children, Queen Key, is unapologetic about her choices when it comes to music.

Fredo Santana is the stage name of popular American rapper Derrick Coleman. Santana is best known also as the older cousin of Chicago-based rapper Chief Keef.

Santana's first mixtape was released on September 20, 2012, under It's a Scary Site. Similarly, his second mixtape was released on February 28, 2013, under Fredo Kruger. 

The Chicago native's debut album was entitled Trappin Ain't Dead. It was released on November 20, 2013. The album also included guest appearances by artists including Kendrick Lamar, Peewee Longway, Chief Kief, and some other members of the Glory Boyz Entertainment.

Santana suffered from serious health issues due to addiction for a prolonged time and eventually passed away in 2018. Even though he had a short time in the industry, Fredo Santana is widely known for his contribution. 

Psalm One is a popular artist Chicago, Illinois. One is best known for being a member of the group named Nacrobats. 

Psalm One is the stage name of rapper Cristalle Bowen. Besides Nacrobats, the rapper is also involved in Rapperchicks and Big Silky.

Raised in Engelwood, the 42-year-old graduated from Whitney M. Young Magnet High School. At the same time, she also achieved a degree in Chemistry from the University of Illinois.

In the year 2006 that she released a studio album entitled The Death of Frequent Flyer on Rhymesayers Entertainment. Some of the popular singles of the rapper include Juke Me, Need Love Too, Impatient, Rules and Regulations, and What I Get For Being Brilliant.

Add-2 is the stage name of the renowned Chicago rappers, Andre D'Juan Daniels. Add became famous for his second mixtape entitled A Tale Of Two's City: Volume 2.

A native of Chicago, he has been in the music industry since 2006. Daniels' single entitled Luxury was released in the year 2009.

Tale of Two's City: Volume 2 was released in 2007. Daniels has collaborated with popular artists, including Grammy Award Winning music producers 9th Wonder and Kendrick Lamar.

In addition, he has also worked with The Roots and Gerald Walker.  The rapper also released the third volume of Tale of Two's City in 2009 and the fourth in 2010.

Rapper Joey Purp is one of the founding members of Savemoney. Purp is more commonly recognized as one-half of the Leather Corduroys.

His original name is Joseph Davis. During his time at Whitney Young High School, Purp realized he had a talent for freestyle rapping.

Joey began his career in 2012 after releasing his first-ever mix tape, The Purple Tape. Similarly, in 2016 he released another mixtape called iiiDrops with contributions from some popular figures like Vic Mensa and Chance The Rapper.

Purp also has several guest appearances in the creation of artists like Donnie Trumpet, Vic Mensa, Louis the Child, and Phantogram. In addition, he has worked as a featured artist in Winners, including Yxng Bane and Chance The Rapper.

Born in 1999, the 24-year-old Polo G is a famous American rapper. Polo G rose to prominence because of his singles entitled Finer Things and Pop out. 

Polo G is the stage name of rapper Taurus Tremani Bartlett. The rapper began his musical journey by releasing an ODA song on YouTube.

It was in 2019 that he released another song named Pop Out, where Lil Tjay was featured as the leading artist. The song peaked and gained number 11 on the Billboard Hot 100.

In addition, its music video successfully got over 200 million views on YouTube.  Taurus has been honored with Forbes 30 under 30 in the year 2021 under the music category.

Chuck Inglish is the stage name of the famous rapper and songwriter Evan Ingersoll.  Inglish is best known for being one of the hip-hop duo The Cool Kids.

He was in the group along with Sir Michael Rocks, whom he met in 2005. Both of them were highly inspired by Golden Age Hip Hop. In addition, they also drew inspiration from artists like LL Cool J and Eric B. & Rakim. 

Speaking of his personal and independent career, the rapper released a mixtape titled Droptops. In October 2013, he released a five-song EP entitled Easily.

In addition, the rapper's debut album, Convertibles, was released in 2014 through Fun Imprint and Federal Prism Records.  The album was developed in collaboration with other important artists like Chance the Rapper, Action Bronson, Ab-Soul, Mac Miller, and BJ the Chicago Kid.

Calboy is the stage name of the 23-year-old rapper from Calvin Lashon Woods, Chicago. The rapper is best known for his viral song Envy Me. 

Woods is a native of South Side, Chicago. Growing up, his family struggled to meet his basic needs. Therefore, the rapper turned his frustration and worries about living below the poverty line as an inspiration and a guiding tool towards music.

It was in the year 2017 that Woods released his debut mixtape under the name The Chosen One. The same year, he released his second mixtape, Anxiety. Woods brought his third mixtape among listeners on June 18, 2018, called Calboy, The Wildboy. 

The rapper claims he is highly inspired by artists such as Chance The Rapper, The Starting Line, Chief Keef, The All American Rejects, and Sherwood Fuel.

Lil Zay Osama is an American rapper who reflects his upbringing through his music. The original name of the 25-year-old rapper is Isaiah Dukes. 

Born and raised in Chicago, Osama had a difficult childhood. Osama started rapping when he was just eight years old. His greatest inspiration was his own brother.

The rapper was 12 years old when he joined a gang. As his gang grew popular, he changed his name and began introducing himself as Lil Zay Osama. 

Osama signed with Warner Records in 2019. After that, he released some works, including Like A Pimp, in collaboration with Stunna 4 Vegas. 

Mick Jenkins is another popular name in the music industry of music in Chicago. Jenkins has signed with the Cinematic Music Group. 

Jenkins' full name is Jayson Mick Jenkins. He was highly inspired and motivated by his parents' musical interests. 

The rapper began his career in 2012 when he released his first official mixtape on January 13, 2012. At the same time, Jenkins also became a member of a hip-hop group named Free Nationals.

It was in April 2013 that the rapper released his mixtape entitled Trees and Truths. Jenkins has also collaborated with rappers like Chance The Rapper and Vic Mensa for the Crossroads project, which gained popularity after its release.

Lucki Camel Jr., popularly known by his stage name gained recognition from his debut project named Alternative Trap. 

Lucki started his journey during his freshman year in High School. According to him, he gains inspiration from famous artists like Chief Keef, Future, and Babyface Ray. After being introduced to the world of music, he dropped out of high school and gave full time to his passion. 

The rapper's debut single was released in 2012 by Untouchable Lucki. It was produced and premiered by the music blog named ELEVATOR. In collaboration with his friends Plu2o Nash and other producers, the rapper released a project named Alternative Trap when he was 17.

Chief Keef is a Chicago rapper who began his journey in the music industry right during his teenage years. 

The original name of Chief Keef is Keith Farrelle Cozart. Keef rose to prominence after he released his mixtape entitled The Glory Road and Bang.

It was in 2015 that the 27 years old released a 20-track mixtape by the name Sorry 4 the Weight. However, in 2016 the popular artist announced that he would retire from rapping.

The news disheartened fans until the rapper reappeared in MGK's song, Young Man. After a break of some time, Keef returned back to the industry and collaborated with different prominent figures, including Jay Z, Nicki Minaj, and Lupe Fiasco.

Rapper Tavares Lamont Taylor is professionally known as Lil Reese. Taylor has been reigning the hip-hop industry of Chicago since the year 2010.

Taylor has been interested in music since his youth and got into the drill scene in the early 2010s. His popularity rose even more when he got an opportunity to collaborate with the famous rapper Chief Keef. 

The collaboration was made for the project entitled I Don't Like. It gained international attention and won the hearts of music lovers from all over the world. 

In addition, Taylor also gained immense recognition from his music videos, including Us and Beef.

Donald Howard Pullen is popularly known by his stage name Rockie Fresh. The rapper is best known for his versatility. 

The rapper began getting immense popularity as his projects became successful one after the other. At the same time, he met Josh Madden in the Bamboozie Festival who helped him a lot in his career.

In 2012, the Chicago native released a mixape called Driving 88. In addition, he also became a part of a Group Project named Electric Highway with several other artists.

Similarly, in 2013 Rockie came up with a project with seven tracks entitled The Birthday Tape. The project was also a celebration of his birthday.

Earl Sweatshirt is a renowned rapper from Chicago, Illinois. Besides being a rapper, Sweatshirt also does record producing and song writing. 

The original name of the rapper is Thebe Neruda Kgositsile. Kgositsile began rapping for the first time while he was in his seventh grade.

He was featured in a song entitled Oldie from the debut album of Odd Future named The OF Tape Vol. 2. Similarly, Kgositsile was also featured in the track named Super Rich Kids from the debut album of Frank Ocean called Channel ORANGE. 

The musical artist is highly acclaimed of his ten-minute track that was released in YouTube under the name Solace. The track was successful in getting more than 100,000 views in 24 hours on the video sharing platform.