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OUR TOURS
We focus solely on the culture, history, and neighborhoods of Chicago’s South Side, aka The Heart of Chicago®
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 OBAMA TOUR
(PART ONE)
This tour traces the footsteps of a young Michelle LaVaughn Robinson, "girl of the south side", from her coming-of-age in South Shore, to her dating years with a charming Barack "Barry" Obama, and through the couple's formative years in the Hyde Park and Kenwood neighborhoods. Guests explore the former residences, institutions and people that influenced their values, leadership and enduring commitment to public service.
*Note: This tour is independently operated and not affiliated with or endorsed by the Obama Foundation.
WHAT TO EXPECT:
Running on Select Dates Starting May 2026 Tour Duration: 2 hours Ticket Cost: $55 per person 📍 Starting Location: South Shore Cultural Center, 7059 S. South Shore Drive, Chicago, IL 60649 Sightseeing of places connected to The Obamas including: ✅ Michelle Obama’s Childhood Home & Grammar School – Learn about her upbringing on the South Side and the family values that shaped her. ✅ Barack Obama’s First Chicago Apartment – See where Barack lived during his early organizing years in Chicago. ✅ The Site of Barack & Michelle’s First Kiss – Visit the iconic location tied to the beginning of their love story. ✅ The Obama Family Residence – See the Kenwood home where the family lived during their rise to the White House and beyond. ✅ University of Chicago Campus – See the campus where The Obamas worked and continued their professional careers. ✅ Insider Stories & Local History – Hear oral history insights from south side residents inspired by their impact. 🚌 Neighborhoods Visited: South Shore, Woodlawn, Hyde Park & Kenwood Discover the places, stories and south side spirit that helped shape one of the most influential couples in modern American history. 👉 Spots are limited—reserve now! *Parking disclaimer: Parking at the South Shore Cultural Center is limited and requires a fee. Availability is not guaranteed. Guests are strongly encouraged to utilize rideshare or public transportation to ensure a smooth arrival experience.
SOUTH SIDE FOOD TOUR:
THE CLASSICS
Embark on a flavor-packed bus journey through the heart of Chicago’s South Side! This 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:
Date: Friday, April 10, 2026 Tour Duration: ~4 hours Ticket Cost: $115 Time: 11am 📍 Starting Location: 38th Place and MLK Jr Drive on the NE Corner (behind the Mariano's parking lot) 🍛 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. 👥 All Ages Welcome! Come hungry and leave with a newfound love for the South Side’s rich culinary scene! 🍴✨ Reserve your spot today! Dietary Restrictions & Refund Policy Most food stops on this tour include meat and/or poultry. Four of the seven stops offer vegetarian options, and our dessert stop includes a vegan option. We are unable to accommodate dietary restrictions, including vegan, gluten-free, Kosher, or other specialized diets beyond the limited options listed above. Guests with food allergies must notify the tour guide before the tour begins. While we will communicate allergies to our restaurant partners when possible, we cannot guarantee an allergen-free environment. No refunds will be issued due to dietary restrictions, food preferences or allergies.
PRIVATE GROUP 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. 🚐✨