Yesterday, our founder appeared on WGN's Spotlight Chicago alongside Qiana Harnett, third-generation Legacy Leader of Harold’s Chicken #14! The segment highlighted a few of the iconic Chicago eateries we'll be visiting on the May 30th South Side Food Tour! We’re incredibly grateful to continue uplifting the south side through tourism, oral history and community experiences — and we couldn’t do it without your support.

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 Wear celebrates the...

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 place — it’s where...