This private architectural walking tour in Chicago explores residences that reflect the city’s design evolution. You will begin along Lake Shore Drive, where early high-rise living reshaped urban life. What architectural movemen... More

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired European styles to bold American Art Deco an... 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

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 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

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 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 art scene of Chicago on the Offbeat Street Art Tour through Fulton Market. This guided walking tour takes you into a neighborhood where industrial buildings have become canvases for stunning murals and installa... 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

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

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 local shopping scene and its fashion DNA with a professional stylist as you embark on a personalized shopping circuit built to meet your style and wishes. Learn more about the art of styling your body features and ta... More

Discover the very best of New York City in one unforgettable experience! From the majestic Statue of Liberty and the historic Brooklyn Bridge to famous neighborhoods, hidden gems, and picture-perfect skyline views — this tour ca... More

Immerse yourself in the vibrant food culture of Chicago with a guided walking tour, led by a knowledgeable local guide. Traverse Downtown's diverse culinary landscape, tracing the influence of immigrants on the city's gastronomy. ... More