Best of Chicago Walking Tour with Skydeck and Boat Cruise

Explore the best way to see the Windy City on foot on our Best of Chicago Walking Tour! Your tour will begin with your local friendly guide meeting you outside of Willis Tower. 

Embark on an unforgettable journey through the heart of Chicago with this comprehensive tour, showcasing the city's most iconic landmarks and architectural marvels.

 Your adventure begins at the renowned Willis Tower, where you'll ascend to the Skydeck. From the 103rd floor, enjoy an awe-inspiring 360-degree view that stretches across 50 miles and includes glimpses of four states. This elevated perspective offers a perfect introduction to the sprawling urban landscape of the Windy City.

 After descending from the Skydeck, your walking tour commences. Stroll towards Millennium Park, and along the way, you'll pass by several points of historical and architectural significance. Marvel at the intricate design of the Rookery Building, renowned for its stunning lobby designed by Frank Lloyd Wright. The Marquette Building follows, its impressive facade and detailed mosaics standing as a testament to the city's rich architectural heritage. Next, encounter the grandeur of the Palmer House, a luxurious hotel with a storied past, before continuing to the Sullivan Center, celebrated for its ornate ironwork and large display windows. Lastly, take in the elegance of the Reliance Building, a pioneering structure in the development of modern skyscrapers.

 As you arrive at Millennium Park, you'll be greeted by the iconic Cloud Gate sculpture. Commonly known as "The Bean," this polished, reflective work of art provides a perfect photo opportunity and a moment to appreciate the blend of natural beauty and urban innovation that defines Chicago.

 Your journey continues with a leisurely walk to Navy Pier. Along the way, you'll cross the historic DuSable Bridge, an engineering marvel offering picturesque views of the Chicago River. Admire the towering Wrigley Building, an iconic symbol of the city's skyline, and take in the bustling activity along the Chicago Riverwalk. Here, the riverfront's vibrant atmosphere provides a scenic backdrop for your stroll. Pass by the Tribune Tower, a neo-Gothic masterpiece that houses fragments from famous structures around the world, adding a unique touch to its exterior.

 Upon reaching Navy Pier, the excitement builds as you prepare to board the Shoreline Architecture Cruise. This narrated boat tour offers an unparalleled perspective on Chicago's architectural treasures. Glide along the scenic waterways, witnessing over 40 of the city's most famous landmarks and hidden architectural gems. Learn about the history and design of these structures, from the classical to the contemporary, as you gain a deeper appreciation for Chicago's rich architectural tapestry.

 This comprehensive tour offers a perfect blend of walking and cruising, providing you with an immersive and engaging experience of Chicago's most celebrated sights. Whether you're an architecture enthusiast, a history buff, or simply looking to explore the city's highlights, this tour promises to be a memorable adventure through the heart of Chicago.

January 09, 2023 - May 13, 2024

Cancellation Policy: standard

Cancellation Cutoff: 24 hours

Cancellation Notes: Full refunds will be offered for cancellations made at least 24 hours prior to departure time. For cancellations made with less than 24 hours to departure time, a $50 cancellation fee per guest will apply.

Best of Chicago Walking Tour

Pick up location is required for all guests. 
Name of lead traveler is required for all bookings. 

Tickets will be held at the box office