Best of Chicago History & Architecture Walking Tour with Boat Cruise

Best of Chicago History & Architecture Walking Tour with Boat Cruise begins with your local guide greeting all the guests at McCormick Tribune Plaza. Your local guide will first lead you to Millennium Park where Cloud Gate (The Bean) is situated. Its a mirrored sculpture that reflects the city’s skyline and the green space around it sets the tone for the best Chicago history tour.

Next, you will descend into the hidden pathways through Chicago Pedway. This network of underground walkways goes beneath the city’s streets and connects buildings, train stations, and civic centers. The Pedway reveals a hidden layer of urban life. As part of a thoughtful Chicago Architecture Walking Tour, it offers insight into how the city’s design supports both daily function and seasonal movement.

After coming out of the tunnels, you’ll step onto the Chicago Riverwalk where you enjoy a leisure walk through the path lined with cafes, public art, and views of some of the city’s most celebrated buildings.

Through the Riverwalk, you will head toward the Magnificent Mile where you’ll encounter some of Chicago’s most iconic buildings such as John Hancock Building, The Wrigley Building, and the Gothic Revival Tribune Tower.

Next you will cross the DuSable Bridge on historic Michigan Avenue as the guide tells you the story of Chicago’s rebirth after the Great Fire. After crossing the bridge, you will arrive at the Starbucks Reserve Roastery where you will have a chance to sample a savory local favorite.

The tour concludes with a relaxing Chicago Boat Cruise tour. As you glide along the water, more than 40 of the city’s architectural landmarks are brought to life through engaging narration. It’s a fitting end to a tour that uncovers not just what Chicago looks like—but how it lives.