Luxury Private Tours | Bespoke Experiences

Chicago grew from a small river-based trading post into a booming multicultural center of commerce and creativity. Although the Great Fire of 1871 devastated much of the young city, it rose from the ashes to become a modern center of opportunity – a reputation it proudly maintains today balancing tradition and innovation, welcoming people and businesses from around the world. Its iconic skyline stands as a testament to the city's resilience and boundless ambition. Uncover the fascinating stories of the Windy City on a custom Chicago private tour.

While much of the city’s original architecture was lost, Chicago moved forward, shaping its own destiny in the form of prominent architecture from Art Deco to Post-Modern. Known as the birthplace of the skyscraper, Sullivan’s structural innovation created an avenue of opportunity for prolific builders influencing diverse Chicago neighborhoods from north to south, including the first 20 years of Frank Lloyd Wright’s impressive career. Explore Chicago’s iconic skyline and architectural marvels on an exclusive Chicago private tour.

With 26 miles of lakefront, 552 parks, beaches, bike trails, and ever-busy streets, Chicagoans enjoy four distinct seasons of entertainment and activity. Five major-league sports teams, the renowned Art Institute of Chicago, grand theaters, an acclaimed symphony center, ethnically diverse cultural neighborhoods, and chic shopping along the Magnificent Mile ensure Chicago’s 40 million annual visitors leave with memories that will last. Experience the vibrant energy of Chicago’s culture on a personalized Chicago private tour.

Whether you choose ninety-five stories above, or several feet under-ground, water-front, curb-side or Michelin-starred, Chicago is home to much more than just deep dish pizza and famous hot dogs. The city’s drinking culture, infamous since Prohibition lets you sneak into a speakeasy from a bygone era for a relaxing cocktail, or indulge your taste for the best of the Midwest’s established microbrewery culture. Indulge in Chicago’s legendary dining scene, from deep-dish pizza to gourmet meals, on a unique Chicago private tour.

Lake Michigan and the Chicago River provide an aqueous backdrop to the manmade structures of Chicago’s picturesque skyline, granting guests an opportunity to explore the Windy City at sunset with a Chicago River cruise from Navy Pier. If you prefer a grounded approach, we’ll bring the family to the vast Botanic Gardens or escape winter’s chill amidst the lush temperate foliage of The Garfield Park Conservatory. Discover the beauty of Lake Michigan and Chicago’s green spaces on a scenic Chicago private tour.