South Side Tours

05/14/2026

Chicago… this one is for the OGs. 💙💚🏙️

Introducing the Memory Lane Tour™ from South Side Tours — a one-of-a-kind experience designed for people with deep Chi-Town roots. Whether it’s your childhood block, grammar school, grandma’s church, the “Rink, or that corner that holds a thousand stories… we’re taking YOU and your people back through the moments that made your Chicago story.

Birthdays. Family reunions. Bachelor/Bachelorettes. Homecomings. Memorials. Just because. 🚍✨

Head to our website for details and fill out an inquiry form to start planning your personalized journey through the city that raised you.

04/29/2026

NOW BOOKING! 🚌✨From legacy to landmarks, food to The Obamas—there’s a tour with your name on it.

Lock in your seat and experience the South Side of Chicago like never before!

Details and tickets for each tour on our website: https://www.southside-tours.com/chicagotour

04/29/2026

NOW BOOKING! 🚌✨From legacy to landmarks, food to The Obamas—there’s a tour with your name on it.

Lock in your seat and experience the South Side of Chicago like never before!

Details and tickets for each tour on our website: www.southside-tours.com

04/28/2026

We’re more than a live-guided tour—we bring oral history to life right on the bus. Here’s a glimpse of the homegrown stories you’ll experience as we move through Bronzeville aka The Low End.

Join us for our next Legacy & Landmarks tour this Sunday, May 3rd at 10AM.

Get your tickets at the link in bio or at www.southside-tours.com.

04/21/2026

WE WON A WEBBY AWARD!!! 🥇🏆🔥🔥🔥

This South Side Story shined through amidst 13,000+ entries from over 70 countries, with 4.6 million votes tallied! A BIG THANK YOU to everyone who voted for Bernard’s Wear!!!

And of course BIG LOVE to Mr. Bernard Shannon of and our fantastic crew:

Angela Dugan () - Producer/Director
Andre Howard () - Cinematographer
Barry Sales () - Editor + Motion Graphics

04/20/2026

‘Twas a beautiful day touring The Black Metropolis aka Bronzeville with this awesome group of activists from across the country. Just a fantastic and knowledgeable group, we love to see it!

Thank you to the for choosing South Side Tours! 💙💚 Maceo Leon Thomas

04/14/2026

When you ride or partner with South Side Tours, you become family! And your experience always matters 🫶💙💚

If you missed our first South Side Food Tour, don’t worry, there’s more to come this summer! Subscribe to our email newsletter to be the first to know of our next run in May!

04/07/2026

Hold up—wait a minute! Yup, we’re bringing some West Side flavor to the South Side Food Tour.

Jessica House of Little Village, is the definition of turning a setback into a comeback. After being laid off from corporate America, she built her catering company from the ground up and is now making an impact across the city.

Catch Jessica on this Friday’s South Side Food Tour and get a taste of the delicious birria tacos she’s serving up!

Watch the full story on our YouTube channel: https://youtu.be/Rmsc1a01zLI?si=W_kJ2_aMj00ySsAW

04/06/2026

Happy Monday! Yes, we’re still nominated for a Webby Award in the Short Documentary-Branded Entertainment category! Vote for Bernard’s Wear () and be a part of amplifying south side Chicago stories!

And be sure to watch the full documentary on our YouTube channel: https://youtu.be/0uDlrXElFB0?si=IScei6IbSI21uIVS

VOTE HERE: https://wbby.co/57535N

04/04/2026

You’ve been fasting and now it’s time to eat good and celebrate good times, C’MON! Hop on the bus with us next Friday, April 10th @ 11am!

We’ll touring through neighborhoods from Chinatown to South Shore and sampling Chicago’s finest family-owned cuisines along the way!

Games, oral history and good times await! 🚌 💙💚

Purchase tickets now @

Choose from a variety of guided tours exploring Chicago’s South Side, including historic sites, cultural landmarks, and hidden treasures. Book your unforgettable tour today!

04/01/2026

SOUTH SIDE TOURS IS WEBBY NOMINATED!! 🔥

Last May we met Bernard Shannon at his shop Bernard’s Wear in the South Chicago neighborhood. We told him we’d be back with a camera. Our founder told him she was going to produce a story about him and his hat business, and submit it to . Well she did that and yesterday we were nominated for a Webby in the Branded Entertainment Documentary category. And honestly we feel like we’ve already won! 🏆🤩🥳

Voting is open until April 16th, so please vote for us at the link here: https://wbby.co/57535N (as many times as your fingers will allow each hour). The full version of the doc is on the South Side Tours YouTube channel: https://youtu.be/0uDlrXElFB0?si=jSMJ7TEck5wHpt1h

Thanks love yall muah! 💙💚💙💚