Best of Chicago Walking Tour
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Best of Chicago Walking Tour

duration-icon4 Hours
people-iconUp to 10 people

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. No trip to Chicago is complete without a visit to the top of the tallest building in the Western Hemisphere - Skydeck Chicago (formerly Sears Tower). You will take the elevator all the way up to the 103rd floor where you will enjoy a spectacular 360-degree view spanning 50 miles and 4 states. Witness the most spectacular view 1,353 feet in the air on The Ledge - special glass balconies extending 4.3 feet outside the building that provide a thrilling, once-in-a-lifetime experience.

What's Included

  • Small group (max 10 people)
  • Visit Skydeck Chicago and The Ledge.
  • Visit Millenium Park to see Cloud Gate Sculpture and Crown Fountain
  • Enjoy a Shoreline Architecture Cruise
  • All attraction admissions lncluded
  • Pass several points of interest including Rookery Building, Palmer House, Chicago Riverwalk, Tribune Tower, Wrigley Bridge and many more

What you'll do

  • 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.

Tour Itineraries

Important Information

Meeting Location 222 South Riverside Plaza - infront of the Fifth Third Center

Please be at the meeting location at least 10 minutes prior to departure

Moderate amount of walking

Exact tour length may vary slightly depending on individual walking speeds

Tour will operate rain or shine. We recommend dressing for the weather and comfortable footwear. You may also wish to bring water

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From $189 USD