Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their history, iconic landmarks, hidden gems, and must-see photo opportunities.... More

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

Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore the neighborhood with a local guide, you'll sample regional Chinese specialti... 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

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

Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walking tour circles Wicker Park, showcasing stunning Victorian mansions o... 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

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

On this private walking tour our expert local guide will take you to see some of Chicago’s best-known attractions! The day will begin with you meeting with your friendly local guide at Millenium Park, home to Cloud Gate.From t... 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