During the Great Migration, more than a half-million Black Americans moved from the South to Chicago, and with them, they brought the blues, amplifying what would be one of the city's greatest musical artforms. In 1958, the iconic Johnson Publishing Company, the voice of Black America, launched the Ebony Fashion Fair show, leading to the creation of the first makeup brand for Black skin. For three decades starting in the 1970s, households across the country were transported to a stage birthed in Chicago as they moved their hips in front of TV screens airing Soul Train.

Chicago is where Oprah Winfrey, a Black woman who did not have the "traditional look" TV managers pushed on talent, premiered her talk show, which went on to break every record possible and solidify her position as the "Queen of Daytime TV." It's where Hall of Famer Michael Jordan led the Bulls to six championships, including two three-peats, making the NBA a must-see attraction worldwide and wearing Jordans a style symbol to this day. And it's home to Grammy winner Chance the Rapper, whose work honors the city's cultural institutions, from the White Sox to modern art superstar Hebru Brantley.