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BOOK A TOUR
THE SOUTH SIDE LEGACY & LANDMARKS TOUR
WHERE DO WE GO?
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.
SOUTH SIDE NIGHT OUT
A Guided Nightlife + Culture Experience presented by South Side Tours!
Grab your crew and come outside! Join us for an elevated night out featuring neighborhood gems and unforgettable vibes.
Come for the night out—leave with a new love for the South Side.
TOUR HIGHLIGHTS:
✨ Curated South Side stops 🎶 Music, culture & nightlife energy 📸 Photo-worthy moments + hidden gems 🍸 Exclusive drink specials for purchase at each stop—only for South Side Tours riders Details: 📅 Date: Saturday, February 14, 2026 Bus Departs: 7pm Bus Returns: Midnight Ticket Cost: $25 plus tax 📍 Starting Location: South Loop; address provided upon ticket purchase 🚌 Where We'll Go: Social Sip Bar & Grill, Park Manor 75 and W. Hideaway Lounge 🔞 21+ Only (Valid ID required)
SOUTH SIDE BREWERY ADVENTURE: BLACK
HISTORY MONTH EDITION
South Side Tours is excited to collaborate with Black and Brew Chicago on this special edition brewery experience in
Black History Month. Enjoy a high-energy, culturally rich brewery adventure that highlights black brewing excellence while incorporating a unique educational component led by beer historian and educator, Mickey Bryant.
Whether you're a beer connoisseur or looking to learn black
brewing history with a buzz, this tour is for you!
COMING SOON
WHAT’S INCLUDED:
✅ Visits to 2 South Side Breweries – Each stop offers unique flavors and brewing styles, showcasing the best local craft beers. Also, receive exclusive behind-the-scenes tours of each facility! ✅ Tasting Flights at Each Brewery – Enjoy a curated selection of beers at every stop. ✅ Onboard welcome brews provided by black-owned breweries across the USA. ✅ Black Brewing History – Hear 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. ✅ Also includes: – Beer + Chicago trivia – Prizes and giveaways – Group photos + social moments Details: 📅 Date: Saturday, February 28, 2026 Tour Duration: ~3 hours 30 mins Ticket Cost: $55 📍 Starting Location: South Loop; address provided upon ticket purchase 🚌 Neighborhoods Visited: Bridgeport and Pilsen 🔞 21+ Only (Valid ID required) 🍿 Snacks Included: Enjoy popcorn, water and black-owned brews on board! 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!
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!
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. 🚐✨
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! 🎈✨
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.
Tour in collaboration with the Richard Hunt Legacy Foundation. For more information click here.
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
THE SECOND ANNUAL
KWANZAA HERITAGE TOUR
Celebrate culture, community, and tradition on the 2025 Second Annual Kwanzaa Heritage Tour, presented in partnership with Chi-Village! Journey through the historic South Shore neighborhood—home to one of Chicago’s earliest Kwanzaa celebrations—as we honor the principles, people, and legacy that make this season so powerful.
TOUR HIGHLIGHTS:
Explore the Seven Principles of Kwanzaa (Nguzo Saba) brought to life through landmark visits, local businesses and immersive storytelling. Enjoy treats from a South Shore bakery with a heartfelt history, and support local entrepreneurs along the way. Whether you celebrate Kwanzaa every year or you're simply curious to learn more about this vibrant cultural holiday, this tour is for you! WHAT’S INCLUDED: ✅ Seven Principles Spotlight – Experience each principle of Kwanzaa through guided storytelling, neighborhood stops, and interactive moments that deepen your understanding of the holiday. ✅ Local Business Connections – Meet South Shore entrepreneurs, learn their stories and support community-owned shops and makers. ✅ Tastes of Tradition – Savor sweet treats from a beloved South Shore bakery—an essential stop on this heritage journey. ✅ Historic Neighborhood Exploration – Discover the roots of one of Chicago’s first Kwanzaa celebrations and the legacy of Black joy and creativity that continues today. Details: 📅 Tour Duration: ~2 hours 📍 Starting Location: South Shore (exact location provided upon booking) 🚌 Neighborhood Highlighted: South Shore 🔆 Family-Friendly: All ages welcome 🍿 Snacks Included: Light refreshments provided; additional treats available for purchase at local businesses. Gather your friends, family, and community and step into the spirit of Umoja (Unity) as we celebrate the beauty of the Kwanzaa season. 👉 Spots are limited—reserve your seat today and experience South Shore like never before!
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.
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!