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Meet The Guides of South Side Tours

Updated: Apr 28

At South Side Tours, we believe that the heart and soul of Chicago’s South Side is best experienced through the voices of those who’ve lived its history. That’s why our tours are led by passionate, local guides, each with a unique perspective on the stories and landmarks that shaped this remarkable community. Meet a few of the voices who bring South Side Tours to life:


Elderly woman in a red beaded jacket smiles warmly. She sits in front of a textured brown wall, exuding a sense of calm and warmth.

FAIREST: Originally from Downsville, Louisiana, Fairest became a nurse at Michael Reese Hospital, a once prominent Jewish hospital and trauma center on the South Side. She shares her journey from rural Louisiana to a life in healthcare, offering insight into one of Chicago’s most vital institutions.


Smiling elderly man in a gray suit sits indoors against a blurred, dark background, conveying a warm and relaxed mood.

ERNEST: A proud “country boy” from Camden, Alabama, Ernest arrived in Chicago after serving in the U.S. Navy during WWII. With firsthand tales of working in the Union Stockyards and casting his first vote in Chicago, Ernest paints a vivid picture of life as a South Sider building his future.


A person in a hat and black outfit sits smiling on a red and cream patterned sofa. Background shows orange and beige decor accents.

ALTHEA: One of the early residents of the Robert Taylor Homes in the 1960s, Althea brings her memories to life through stories of old-school parenting, community and resilience in the face of challenges. Her captivating storytelling transports guests to a nostalgic era of Chicago history.


Smiling woman sitting on a Victorian-style red floral couch. Warm, cozy setting with a large vase and orange drapery in the background.

ANGELA: As the founder of South Side Tours, Angela fills in the blanks of how the South Side became a haven for African-Americans during The Great Migration, especially Bronzeville. Through her own family’s history, Angela shares how Chicago became home to many Mississippians during the early 20th century.


Experience the South Side from a true insider’s view – each tour offers a unique narrative of migration, resilience, and community spirit. Don’t miss your chance to connect with these living legends and learn from the voices that shaped Chicago’s story.


More Than a Tour. A Journey Through History.

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