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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

Dear Friends of South Side Tours, As Black History Month comes to a close, we are proud to share a special moment from this meaningful season. This past Sunday, February 22nd , our founder, Angela Dugan, was honored to serve as the keynote speaker for the People’s Church of the Harvest COGIC Black History Month Presentation. Angela delivered a powerful and engaging talk commemorating the centennial of Black History Month, connecting national history with the rich and often

Hey friends! Did you catch us on WGN’s Spotlight last week?! We were so excited to be featured in Mama Fresh’s incredible roundup of Black History Month family events : As Mama Fresh reminded us, “Black history is happening every day!” That message is at the heart of everything we do. We’re honored to share Black history with our community through our interactive South Side tours , where learning truly comes alive—and yes… we do love a good pop quiz 😉. We’ve also been bu

We’re honored to share that South Side Weekly recently featured South Side Tours and our founder, Angela Dugan , in a beautifully written three-page spread by Dierdre Robinson. The South Side is a place rich with history and creativity, and we’re deeply grateful to be part of the ecosystem that helps tell its stories. This work has always been a family affair—and a true labor of love. Thank you to South Side Weekly and Dierdre for seeing our mission so clearly and for shari

📅 Date: Saturday, February 14th ⏰ Time: 7pm 📍 Meeting Point: South Loop (address revealed upon ticket purchase) 📣 There are still a few spots left! Grab yours before they’re gone. Valentine’s and community vibes? Yes please! 💃✨ Our South Side Night Out tour is happening this Saturday, and we’re inviting you to spend an unforgettable evening experiencing the best of Chicago’s south side nightlife — including visits to Black women–owned lounges , curated spaces where cu

Happy Black History Month, South Side Tours family! As we enter this month, we want to first wish you joy, reflection and pride. Black history is American history — full stop. Our stories are foundational, powerful and ongoing. At the same time, we would be remiss not to acknowledge that our history is under attack. The recent removal of chattel slavery interpretive panels from the "President’s House: Freedom and Slavery in the Making of a New Nation" exhibit in Philadelp

Hi South Side Tours Family, We’re excited to share that we were featured live in-studio on WGN News Neighborhood Spotlight ! 🎥✨ If you missed it, the segment is a quick look at why we do this work—and a perfect preview of what you’ll experience on our Kwanzaa Heritage Tour . Watch the WGN Neighborhood Spotlight segment: NEWLY ADDED: Kuumba Soul Choir Performance — December 20th Tour Date ONLY ! We’re thrilled to announce a special addition to the December 20th tour date : �

🥳 We’re BAAAACCKK! The Kwanzaa Heritage Tour Returns for Year 2! 🚌✨ South Side Tours is excited to partner once again with Chi Village to bring you the Second Annual Kwanzaa Heritage Tour —a joyful celebration of culture, community, and tradition right in the heart of South Shore. ❤️🖤💚 Experience Kwanzaa Like Never Before This year’s tour brings the Seven Principles of Kwanzaa (Nguzo Saba) to life through landmark visits, local businesses, and immersive storytelling. F

We are thrilled to announce our next FREE community tour of historic Bronzeville , guided by the brilliant storyteller and historian, Maceo Leon Thomas ! This special experience is one of our favorite gifts to the greater Chicago community—an opportunity for everyone to learn, connect, and explore the neighborhood we lovingly call “The Low End.” Step aboard our beautiful, comfortable bus and get ready for a journey through one of Chicago’s most culturally rich and influentia

We’re thrilled to debut our newest Heart of Chicago® story featuring Bernard Shannon, owner of Bernard's Wear, a staple in the South Chicago neighborhood. Discover the values that shaped Bernard’s business—and how they capture the spirit of Chicago itself. He reflects on his coming-of-age along historic Maxwell Street and shares how navigating today’s global market presents new challenges for the future of Bernard’s Wear. 🎥 Watch Bernard’s story: Now Touring - Sculpting A L

South Side Tours was honored to provide transportation for the unforgettable Underground Railroad Tour of DuPage County , presented on...

We had an incredible time celebrating the birthday of legendary sculptor Richard Hunt on our Sculpting A Legacy: Richard Hunt & The Soul of Chicago tour! Together with Jon Ott & D.Lamar Preston, we honored Hunt’s legacy and explored his iconic works from downtown to the South Side — connecting art, history and community in a way only Chicago can.

Our Sculpting a Legacy: Richard Hunt & the Soul of Chicago bus tour runs on select dates through November 15th —but we have something...

We are thrilled to announce a powerful new guided bus tour celebrating the life, legacy, and artistry of Richard Hunt — the most...

Chicago is alive with stories waiting to be discovered—and we’re bringing them to you in unforgettable ways. 📍 Reserve your spot now! ...

Big news — South Side Tours was recently featured by Tourism Cares , and we’re thrilled to share more about our journey with you. Our...

We’re thrilled to share the incredible momentum South Side Tours has built this month — thanks to powerful partnerships, cultural...