The neighborhood, which is a part of Bronzeville, is one of the most historic African-American communities in the country.
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Her guide in Douglas was one of the city's most unique and prominent historians - Sherman "Dilla" Thomas.
Dilla, known online as "6Figga Dilla", is known for his TikTok videos on Chicago history, which have been seen by hundreds of thousands of viewers.
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He took Val from the Victory Monument at 35th Street and Martin Luther King Drive to the former home of the Sunset Café at 35th Street and Calumet Avenue - one of the most historic former jazz venues in the country.
They then walked down the 3600 block of Martin Luther King Drive, where they visited the home of pioneering Black journalist Ida B. Wells.
Then they visited one of the first YMCA's in the U.S. to open its doors to Black patrons, before ending up at the Monument to the Great Northern Migration statue at 26th and King Drive.