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BOOK A TOUR
OUR TOURS
We focus solely on the culture, history, and neighborhoods of Chicago’s South Side.
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 – 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: 3 hours (includes bathroom break) 👥 All Ages Welcome Note: This tour is a sightseeing experience only.
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 three 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 3 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: ~3 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!
BREWERY ADVENTURE
Experience the rich craft beer culture of the South Side on this immersive brewery and history tour. Visit top-rated local breweries and enjoy tasting flights of signature and seasonal beers while also hearing about the bootlegging, baseball and blues history from Bridgeport to Bronzeville!
Whether you're a beer connoisseur or looking to learn some good ol' Chitown history with a buzz, this tour is for you!
WHAT’S INCLUDED:
✅ Visits to 3 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. ✅ Insider Experience – Learn about the owners of each brewery, their story and how they came to brewing on the south side. ✅ South Side History – Travel from Bridgeport to Bronzeville hearing hidden history and hilarious lore as told by our guide who's also a VIBE! ✅ 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: ~3 hours 30 mins 📍 Starting Location: Southwest corner of Wabash Avenue and Monroe Street 🚌 Neighborhoods Visited: Bridgeport, Bronzeville, Back of the Yards 🔞 21+ Only (Valid ID required) 🍿 Snacks Included: Enjoy popcorn & water on board as you explore! Food also available for purchase at select breweries. 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!
SUMMER STROLL
A journey through power, place and possibility! This special experience features:
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Highlights of Bronzeville’s historic landmarks
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A visit through Hyde Park/Kenwood, home to the Obamas
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Stops at Theaster Gates’ Rebuild Foundation public spaces
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A culturally immersive event to conclude the tour
WHAT’S INCLUDED:
🚍 Guided Bus Tour – Mixture of live guide and media offering engaging commentary, historic insights, and insider stories. 📅 Tour Duration: 3 hours 👥 All Ages Welcome
COMING SUMMER 2025
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!
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. 🚐✨
TICKET SCHEDULE
Tours are offered daily, click on the tour options above to see information for each. You can pick-up the tour at the southwest corner of Wabash Avenue and Monroe Streets.