By sheer coincidence, the city of Chicago presents a unique opportunity for visitors to embark on a Small Group Walking Tour with Skydeck and Boat, an experience that promises to unveil the city’s most iconic sights.
Led by a knowledgeable local guide, this tour combines the thrill of ascending to the 103rd floor of the Skydeck Chicago, walking on glass balconies, and enjoying sweeping views of the city, with a leisurely boat cruise along the Chicago River.
But this tour is more than just a series of breathtaking vistas; it offers a chance to take in the rich history and architectural wonders of Chicago, from Millennium Park’s art installations to the vibrant atmosphere of Navy Pier.
With a maximum of 10 participants, this intimate tour ensures an expertly curated exploration of the city’s highlights.
Good To Know

- The tour includes a visit to Skydeck Chicago, the tallest building in the western hemisphere, where participants can enjoy panoramic views and experience The Ledge, glass balconies extending outside the building.
- Participants will have the opportunity to explore Millennium Park, home to beautiful gardens and attractions such as the iconic Cloud Gate Sculpture.
- The tour also includes a visit to Navy Pier, which offers a variety of entertainment options such as dining, retail, and attractions.
- Participants will have the chance to take a Shoreline Architecture Cruise, where they can admire Chicago’s famous skyscrapers and iconic landmarks while enjoying a narrated boat tour.
Activity Details and Inclusions

The activity details and inclusions for the Chicago Walking Tour with Skydeck and Boat are designed to provide participants with a comprehensive and immersive experience of the city’s iconic landmarks and attractions.
This small group tour allows for a more personalized experience, with a maximum group size of 10 participants. The tour has a duration of 2.5 hours, giving participants ample time to explore and enjoy each stop along the way.
The tour starts outside Willis Tower, where you will visit Skydeck Chicago and experience The Ledge, glass balconies extending outside the building.
The tour then continues to Millennium Park, Navy Pier, and concludes with a Shoreline Architecture Cruise, offering panoramic views of over 40 iconic landmarks.
All attraction admissions are included in the tour, making it a hassle-free and enjoyable experience for participants.
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Experience Highlights

Starting the Chicago Walking Tour with Skydeck and Boat provides participants with an unforgettable experience of the city’s most iconic landmarks and attractions.
The tour begins outside Willis Tower, where you will visit Skydeck Chicago, the tallest building in the western hemisphere. A thrilling experience awaits as they take an elevator to the 103rd floor and step onto The Ledge, glass balconies extending outside the building.
Next, you will explore Millennium Park, home to stunning art installations and gardens, including the iconic Cloud Gate Sculpture.
A visit to Navy Pier offers a wide range of entertainment options, and the tour culminates with a Shoreline Architecture Cruise, providing breathtaking views of over 40 iconic landmarks along the Chicago River.
Participants can expect a small group setting, ensuring an intimate and personalized experience.
Tour Itinerary

Participants will embark on an exciting journey through Chicago’s most famous landmarks and attractions with the Tour Itinerary.
Start the tour outside Willis Tower with a friendly local guide.
Visit Skydeck Chicago, the tallest building in the western hemisphere, for a 360-degree view spanning 50 miles and 4 states.
Experience The Ledge, glass balconies extending outside the building, for a thrilling experience.
Explore Millennium Park and see stunning art installations, including the iconic Cloud Gate Sculpture and Crown Fountain.
Head to Navy Pier for a wide range of entertainment, dining, and retail options.
Hop aboard a Shoreline Architecture Cruise to witness the beauty of Chicago’s famous skyscrapers and iconic landmarks from the Chicago River.
Throughout the tour, you will have a knowledgeable guide providing live commentary and insights about the tour highlights and recommended attractions.
The tour ends with the guide bidding farewell to the participants, leaving them with unforgettable memories of Chicago’s architectural wonders.
Meeting Point and Logistics

Embarking on the exploration of Chicago’s famous landmarks and attractions, you will need to know the meeting point and logistics for this exciting tour. The meeting point for the tour is in front of The Willis Tower, where you will find their friendly local guide wearing a white polo shirt with the company logo. It is recommended that participants arrive 10 minutes prior to the start time to ensure a prompt departure. The tour operates rain or shine, so participants should come prepared for the weather. The exact tour length may vary depending on walking speeds, but the duration of the activity is 2.5 hours. Participants can check availability for their desired date of the tour during the booking process. With a small group activity limited to a maximum of 10 people, this tour offers an intimate and personalized experience of Chicago’s iconic landmarks.
| Meeting Point | Logistics |
|---|---|
| In front of The Willis Tower | Guide wearing a white polo shirt with the company logo |
| Participants arrive 10 minutes prior to the start time | Tour operates rain or shine |
| Duration of the activity is 2.5 hours | Small group activity with a maximum of 10 people |
| Check availability for desired date | Intimate and personalized experience |
Booking and Availability
To book this Chicago walking tour and check availability, simply select your desired date and number of participants during the booking process. Once you have chosen your date and group size, you can proceed with the reservation. It’s recommended to book in advance to secure your spot on the tour.
The tour operates rain or shine, so you can plan your visit regardless of the weather. Free cancellation is available up to 24 hours in advance, giving you the flexibility to change your plans if needed.
Please note that the tour is conducted in English and is wheelchair accessible for people with mobility needs. With a maximum group size of 10 participants, you can expect a personalized and intimate experience throughout the tour.
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Common Questions
Is Transportation Provided Between the Different Attractions on the Tour?
Transportation logistics are not provided between the attractions on the tour. Participants will walk between the different sites as outlined in the tour itinerary.
Are Food and Drinks Included in the Tour?
Food and drinks are not included in the tour. However, you will have the opportunity to explore various dining options at Navy Pier. Transportation between attractions is not provided as this is a walking tour.
Are There Any Age Restrictions for Participating in the Tour?
There are no age restrictions for participating in the tour. The activity is wheelchair accessible, ensuring that people with mobility needs can also enjoy the experience.
Is Photography Allowed During the Tour?
Photography is allowed during the tour, but there may be restrictions at the Skydeck. Visitors are advised to check the specific photography policy at the Skydeck Chicago for any guidelines or limitations.
Can I Bring My Own Wheelchair or Is One Provided for the Wheelchair Accessible Parts of the Tour?
Yes, participants can bring their own personal wheelchair. The tour is wheelchair accessible, and there are provisions made for wheelchair accessibility during the tour.
The Sum Up

To sum it up, the Small Group Walking Tour with Skydeck and Boat in Chicago offers a unique and immersive experience for visitors.
With the opportunity to explore iconic landmarks, including the Skydeck Chicago and Millennium Park, participants can enjoy breathtaking views and learn about the city’s rich architectural history.
With a small group size, this tour ensures a personalized and informative journey through the vibrant city of Chicago.
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