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

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

Uncover the chilling history of Chicago's gangsters and ghosts on this thrilling late-night Halloween walking tour. Delve into the dark secrets of the South Loop, once a vice district, as your historian guide shares captivating ta... More

This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy to customize the tour itinerary and content for your group. Discover the amazing hist... More

Bucktown has a knack for keeping secrets - and most of them are deeply unsettling. On this self-guided walking tour, you'll hear the true stories behind the neighborhood's murders, hauntings, and disappearances, encountering a rea... 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

Explore Chicago with a passionate local guide on a small-group walking tour that takes you beyond the city's most recognizable landmarks. As you stroll through the heart of the city, you'll uncover fascinating stories, admire worl... 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

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

Visit the most beautiful interiors in Chicago with a local guide bringing their stories to life. Step into stunning centuries-old architecture on a guided walking tour of downtown Chicago. We go in buildings no other walking tou... 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 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident, you will discover the neighborhood’s transition from a wealthy enclave to a gritty artist ... 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

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

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

Leave the city's hustle behind and embrace the tranquility of Mackinac Island, a destination where cars are absent, and the charm of horse-drawn carriages prevails. This tour includes a beautiful drive through the Midwest and a sc... More

This private family walking tour in Chicago introduces the cultural and architectural identity of the Loop district. You will begin in the financial center, where early skyscrapers reflect economic ambition. How did Chicago become... 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

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

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