All Posts

We’re proud to share that South Side Tours is officially a Webby Award Winner for Best Short Documentary in the Branded Entertainment category for Bernard’s Wear! 🎉 Thank you to everyone who took the time to vote and support this story. Out of 13,000+ entries from more than 70 countries and nearly 5 million votes cast, this South Side Story stood out on the global stage — a powerful reminder that stories rooted in community resonate far beyond our neighborhoods. Bernard’s We

Hello Friends, South Side Tours is proud to introduce a brand new offering designed especially for people who have deep roots in Chicago: 🚍 Your Legacy Tour™ Celebrate your story with a one-of-a-kind journey through the places that shaped your life. Your Legacy Tour™ is a fully custom South Side experience that takes you and your guests through the neighborhoods and local spots that hold your most meaningful memories. For many Chicagoans, the South Side is more than a pl

We’re excited to share that South Side Tours has been nominated for a Webby Award in the Branded Entertainment Documentary category for Bernard’s Wear ! 🎉 Bernard’s Wear tells the story of Bernard Shannon , a beloved hat shop and clothier located in the South Chicago community , known for timeless style, craftsmanship, and decades of service to generations of customers. The film celebrates both the legacy of the shop and the cultural significance of neighborhood institut

South Side Tours is excited to introduce two brand-new experiences launching this season , each offering a different way to explore the culture, history and flavors of Chicago’s south side. 🏛 The South Side Obama Tour $55 per person, 2 hours Now Booking for May 2026 Step into the neighborhoods that shaped the early lives of Michelle and Barack Obama. This tour traces Michelle LaVaughn Robinson’s coming-of-age in South Shore as a proud “girl of the South Side,” her early c