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THE SOUTH SIDE LEGACY & LANDMARKS TOUR

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LEGACY & LANDMARKS TOUR

Discover the rich history, culture, and iconic landmarks of Chicago’s South Side on our Legacy & Landmarks Tour! From the heart of the Bronzeville Historic District to the former home of Barack and Michelle Obama, this tour takes you through the places that have shaped Chicago—and the nation.

TOUR HIGHLIGHTS:

📍 Bronzeville Historic District – Explore the birthplace of Chicago’s Black Renaissance and its lasting cultural impact. 🏡 Ida B. Wells & Emmett Till Homes – Stand in the footsteps of history and learn about these courageous figures. 🏛️ Obama Family Home (Kenwood) – See the residence of the 44th President and First Lady. ⚾ Guaranteed Rate Field (White Sox Stadium) – A stop for sports lovers at the home of the South Side Sox. 🐂 Union Stockyards – A glimpse into the past of Chicago’s booming meatpacking industry. 🎓 53rd Street Commercial Corridor – See Downtown Hyde Park’s critically-acclaimed small businesses 🌳 Washington Park – A beautiful green space with deep historical and cultural significance. 🚍 Guided Bus Tour – Engaging commentary, historic insights, and insider stories. 📅 Tour Duration: 2 hours and 45 minutes (includes bathroom break) 👥 All Ages Welcome Note: This is sightseeing only. No hop-on, hop-off capabilities.

SCULPTING A LEGACY:

RICHARD HUNT & THE SOUL OF CHICAGO

Step into the story of Chicago through the eyes — and art — of the most commissioned sculptor in the country, Richard Hunt. This guided experience journeys through downtown Chicago and the South Side, where Hunt’s roots and inspiration run deep. 

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Tour in collaboration with the Richard Hunt Legacy Foundation. For more information click here.

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WHAT’S INCLUDED:

🖤 Explore Hunt’s iconic public works across Chicago 🏛 Visit historic landmarks, including:  • The Emmett Till Home  • Roberts Temple (site of Emmett Till’s funeral)  • Richard Hunt’s childhood home  • Obama Presidential Center (future site of Hunt’s work) ✨ Get exclusive access to LUMA’s current exhibition showcasing Hunt’s studio creations & archives 📅 When: Wednesdays–Sundays @ 1:30pm, starting September 3rd 🎟 Price: $55; includes admission to the Loyola Museum of Art (LUMA) exhibit, Freedom in Form: Richard Hunt 📍 Chicago, IL

BREWERY ADVENTURE

Explore the Best Breweries on Chicago’s South Side! Join South Side Tours for an unforgettable brewery adventure, where we take you to four of the best craft breweries on the South Side! Whether you're a seasoned beer enthusiast or just looking to sip and explore, this bus tour is the perfect way to experience Chicago’s thriving craft beer scene.

WHAT’S INCLUDED:

✅ Visits to 4 South Side Breweries – Each stop offers unique flavors and brewing styles, showcasing the best local craft beers. ✅ Tasting Flights at Each Brewery – Enjoy a curated selection of beers at every stop, from hoppy IPAs to rich stouts and everything in between. ✅ Guided Experience – Learn about the brewing process, the history of each brewery, and fun facts about Chicago’s history and culture. ✅ Safe & Fun Transportation – No need to worry about driving—we’ll handle the logistics while you sit back, relax, and enjoy the ride. Details: 📅 Tour Duration: ~2.5 hours 📍 Starting Location: Southwest corner of Wabash Avenue and Monroe Street 🔞 21+ Only (Valid ID required) Gather your friends and raise a glass to the best breweries the South Side has to offer! 🍺 Book your spot today and get ready to sip, savor, and explore. 👉 Spots are limited—reserve now!

STAPLE FOOD TOUR

Embark on a flavor-packed bus journey through the heart of Chicago’s South Side! The South Side Staple Food Tour takes you to seven incredible restaurants, each showcasing a unique heritage and cuisine. From pizza to fried chicken with mild sauce, classic custard to globally inspired bites, this tour is a celebration of the diverse cultures that make the South Side a true foodie destination.

WHAT TO EXPECT:

🍛 Seven Stops, Seven Cultures – Experience a variety of authentic dishes from family-owned and iconic eateries. 🥘 A Taste of Tradition – Discover the stories behind the cuisines and the communities that bring them to life. 🚌 Guided Culinary Experience – Taste and explore with expert guides sharing South Side history and food culture. 📅 Tour Duration: ~4 hours 📍 Starting Location: Southwest corner of Wabash Avenue and Monroe Street 👥 All Ages Welcome! Come hungry and leave with a newfound love for the South Side’s rich culinary scene! 🍴✨ Reserve your spot today!

BIRTHDAY LEGACY TOUR

Celebrate your special day with a one-of-a-kind journey through the places that have shaped your life! Our Birthday Legacy Tour is a personalized South Side adventure, taking you and your guests to the landmarks, neighborhoods, and favorite spots that hold meaningful memories—from your childhood block to your go-to restaurant, school, or favorite hangout.

WHAT’S INCLUDED:

🎂 Custom Itinerary – Tell us the places that matter most, and we’ll design a route that brings your story to life. 🚍 Private Bus for Your Group – Travel in comfort while reminiscing and making new memories. 📍 Stops at Key Locations – Whether it’s your old school, a beloved park, or the restaurant where family traditions began, we’ll make sure to hit all the highlights. 🎤 Guided Experience – Share your personal stories, or let our guide highlight the history and culture of your South Side journey. 🍽️ Optional Food & Drink Stops – Add in a special meal or toast to the occasion at your favorite local spot. 📅 Flexible Scheduling 👥 Perfect for Any Group Size 🎊 A Unique, Heartfelt Celebration Make your birthday celebration unforgettable by taking a tour through the places that shaped who you are. Book your Birthday Legacy Tour today! 🎈✨

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CUSTOM BUS TOUR

Pick your destinations or vibe, and we’ll handle the rest! From food and history to nightlife and culture, the choice is yours. Allow us to curate an authentic and unforgettable South Side experience for your group or organization!

WHAT TO EXPECT:

Private Bus for Your Group – Comfortable, convenient, and stress-free transportation. 🍽️ Food & Drink Options – Add stops at top restaurants, bars, or breweries for a delicious experience. 🎤 Engaging Guides – Fun, knowledgeable hosts share stories and insider tips along the way. 📅 Flexible Scheduling 👥 Perfect for Any Group Size 📍 Pickup & Drop-off Arranged for You Let’s make your event unforgettable! Contact us today to plan your custom South Side tour. 🚐✨

PLACES OF INTERESTS

Home of Civil Rights trailblazer, Ida B. Wells

The Obamas former residence

Emmett & Mamie Till-Mobley Home

The Famous Union Stock Yards

Ride the Bud Billiken Parade route and more!

TICKET SCHEDULE

Tours are offered Saturday and Sunday beginning promptly at 11am, ending approximately at 1:45pm. You can pick-up the tour at the southwest corner of Wabash Avenue and Monroe Streets. There are no hop-on, hop-off capabilities.

Check out Tour Disclaimer

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