Chicago: Small Group Walking Tour with Skydeck and Boat

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Explore the highlights of Chicago on a guided tour that includes a stroll around town as well as a boat cruise on the Chicago River. Learn about the history of the city in a small group from an expert guide.


  • Visit the tallest building in the western hemisphere Skydeck Chicago
  • Take an elevator to the 103rd floor to enjoy panoramic views and experience The
  • Head to Millenium Park to see beautiful gardens, attractions, Cloud Gate Sculptu
  • Make your way to the Navy Pier to hop aboard a Shoreline Architecture 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. 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. Once your feet are back on solid ground, you will head to Millennium Park. You will love this urban oasis with its stunning art installations, gardens, and attractions. Featuring the iconic Cloud Gate sculpture, interactive Crown Fountain, and free cultural events, the park offers a vibrant atmosphere and impressive skyline views that make it a must-visit destination. You will then make your way to Navy Pier. What was once a shipping and recreational facility, now offers a plethora of entertainment, dining, and retail options, including a Ferris wheel, boat cruises, museums, theaters, and outdoor parks and gardens, making it a must-visit destination for people of all ages. For your last stop, you will get to witness the beauty of Chicago's architecture by seeing world-famous skyscrapers from the Chicago River. Hop aboard the Shoreline Architecture Cruise to enjoy a narrated boat tour where you will see the breathtaking views of over 40 Chicago iconic landmarks, from hidden architectural features to the Windy City's most famous monuments. Once you are back on dry land, your tour will come to a close and you and your guide will part ways.


Small group (max 10 people) Visit Skydeck Chicago and The Ledge Millenium Park to see Cloud Gate Sculpture and Crown Fountain Visit Navy Pier Enjoy a Shoreline Architecture Cruise All attraction admissions lncluded

Important Information

  • 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 Please arrive at the meeting location 10 mins prior to the start time of the tour Attractions operations may change based on seasonality

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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