The Bloomingdale Trail was built on a former railway line that once served as the industrial backbone of Chicago's north side. On this self-guided audio tour through Bucktown and Wicker Park, you'll hear how the factories, immigra... More

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Bridgeport /Stockyard Tour, led by Historian Dilla, who uncovers the unique stories and contributions of t... More

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic skyscrapers and stunning lobbies, learning the fascinating stories behind... More

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like North Lawndale, led by Historian Dilla, who uncovers the unique stories and contributions of these communi... More

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which provides a unique and interesting touch to the normal tour experience. Bei... More

Explore Chicago's iconic skyline on this enlightening Riverwalk architectural tour. Experience the rich tapestry of history and innovation as "you get your steps in" along the scenic Riverwalk, revealing the stories behind the cit... More

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Chatham, led by Historian Dilla, who uncovers the unique stories and contributions of these communities, p... More

More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't always accurate. On this tour, you’ll hear how the culture in turn-... More

This private architectural walking tour in Chicago reveals a city shaped by cultural ambition and design excellence. You will begin at the historic Cultural Center, where a grand stained-glass dome reflects artistic heritage. How ... More

Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary theatre district, this tour brings the city’s spirit to life—one ste... More

Uncover Chicago’s bold spirit through its iconic landmarks, from the Gothic Holy Name Cathedral to the gleaming Cloud Gate. Hear untold stories of resilience, art, and innovation. Optional: see the Chicago Theatre, Cultural Cent... More

This unique tour will give you a complete overview of Chicago's architecture. While listening to the history of the city, you will see, in chronological order, some of its oldest buildings, as well as ultra-high towers of recent c... More

To me, one can appreciate a given building, or piece of public sculpture, far better when a tour guide explains the historical and cultural context. What was important in that era, and what was the architecture of that era thus tr... More

Winner of 10 Best History Tours by USA Today in 2026, and the "ORIGINAL" Chinatown tour since 2001. Discover the history, culture, and hidden stories of Chicago’s Chinatown on a guided walking tour through one of the city’s ... More

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient pickup and enjoy a scenic drive as your expert guide shares insig... More

Discover the unique journey of Pope Leo XIV through Chicago on this interactive bus tour. Visit his childhood home and childhood church in the suburb of Dolton on this one of a kind experience. This tour not only showcases the Pop... More

Skip the crowds this is a private tour for your group only! Embark on a captivating journey through the Loop’s architectural wonders with our Loop Architecture Tour in Chicago. Explore the iconic Chicago Board of Trade Building ... More

Explore the charm of Mackinac Island on this delightful journey from Chicago. Experience a blend of history, culture, and stunning landscapes as you travel through the Great Lakes region. Discover the island's unique features, whe... More

Step into the eerie past of Chicago on this thrilling 2-hour private ghost tour led by a local through the haunted corners of the Lincoln Park area.... More

Do you love 80's movies? Explore Chicago’s cinematic history with an engaging scavenger hunt that takes you through the iconic Loop and River North. This activity invites participants to connect with the city’s rich film legac... More