Best of Chicago Exclusive Private Tour

The Best of Chicago Exclusive Private Tour offers a comfortable and thoughtfully guided introduction to the city’s most iconic sights. Over the course of four hours, guests are taken through a curated journey that combines architecture, history, and views—all in the company of a local guide and a private vehicle.

It’s designed for small groups who prefer an efficient but enriching way to explore the Windy City.

Your experience begins at Skydeck Chicago, located on the 103rd floor of the Willis Tower, formerly known as the Sears Tower. From this vantage point, visitors can take in 360-degree views that stretch across four states on a clear day. One of the highlights is The Ledge—a series of glass boxes that extend outside the building, offering a thrilling perspective straight down. It's a quiet but striking moment, standing over 1,300 feet above the city, taking in just how vast and varied Chicago’s landscape truly is.

From there, the tour continues to the Adler Planetarium Pier, not for its space exhibits, but for the views. This spot offers one of the best panoramic angles of the Chicago skyline, with Lake Michigan providing a clean backdrop behind the clustered high-rises. It’s not just a photo opportunity—it’s a place to pause and admire the precision and ambition that shaped Chicago into the architectural capital it is today.

Next, guests board the Shoreline Architecture Cruise. This narrated boat ride down the Chicago River is one of the city’s most celebrated experiences. The cruise highlights more than 40 landmark buildings and offers insight into how Chicago’s skyline came to be—blending historical context with details about style, materials, and design. It’s an informative yet gentle ride, where even those with no background in architecture can walk away with a better appreciation of the city.

Back on land, the tour makes its way to Buckingham Fountain in Grant Park. One of the largest fountains in the world, its design was inspired by the Latona Fountain at Versailles. When active, the fountain’s water displays are choreographed with lights and music, though even in stillness, its presence is grand and grounding.

The final stop is Cloud Gate, more commonly known as “The Bean.” This polished stainless steel sculpture reflects the city and its visitors in playful, warped reflections. Created by artist Anish Kapoor, it has become a symbol of modern Chicago—interactive, imaginative, and accessible.

Each stop offers something different: a view, a story, a moment of reflection. Together, they create a well-paced, meaningful experience of Chicago.