Phone
+44 203 026 1075

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Chicago, US
91% of travellers recommend this
Excellent (32 reviews)
Self-guided - entry to attractions not included
Image not available
Image not available
Image not available
Image not available
Image not available
Image not available
1 / 1
/ Person
1

Your Product

Select participants
Infant (0-0)
Min: 0 Max: 30
Child (1-12)
Min: 0 Max: 30
Adult (13-99)
Min: 1 Max: 30
You should select a minimum of and a total maximum of
At least one participant is required. Please adjust and try again.

Non-refundable - Your booking can not be cancelled, modified or refunded.

Guaranteed Lowest Prices - Find a lower price? We'll match it!

    Highlights

    • Sailing adventure on Lake Michigan
    • Breathtaking views of Chicago skyline
    • Enjoying the fresh air on the water
    • Restroom available on board
    • Convenient location near dining options
    • Duration 1 hour 15 minutes
    • Restroom on board
    • Expert Guide in English
    • Moderate fitness level required
    • Public transport nearby

    Embark on a thrilling Chicago Skyline Sail on Lake Michigan with this unforgettable Tall Ship Windy sailing tour. Feel the wind in your hair and breathe in the fresh air as you take in the stunning views of the iconic Chicago skyline. With a restroom on board for convenience, all you have to do is sit back, relax, and enjoy the adventure. Book now for an experience you won't soon forget!

    At a Glance

    • 1 hours 15 minutes
    • Instant Confirmation
    • Available in English
    • Mobile voucher
    • Small Group tour
    • Self-guided
    • Family friendly

    Featured Reviews

    Excellent (32 reviews)
    icon
    Viator
    Mychaela K
    Jun 25
    A beautiful skyline cruise! We had great views for family photos and they gave us an opportunity to rise the sails which was cool, we took pictures steering the ship and enjoyed drinks from the bar below deck!! I loved it but I can see how it wouldn’t be some peoples cup of tea🤷🏼‍♀️ Overall the crew was super nice and interactive the whole ride!! If you’re looking for a cruise that’s more informative I’d try one of the architecture cruises or tours!
    icon
    Viator
    kimhB391FJ
    Jun 25
    The experience and the views were amazing but the entire crew was incredible. Michael at the ticket booth entertained the grandkids while we were in line teaching them how to tie a knot. Cristian on the crew told them pirate stories on the ride. Zack and the captain were also great. I highly recommend the Tall Ship Windy!!!
    icon
    Viator
    kristinaf955
    Jun 25
    This was my third time sailing on the Tall Ship Windy, and it never disappoints! I keep coming back because whenever I tell family and friends about it, it’s the first thing they want to do when we're in Chicago. This time, I brought my mom, my sister, and my nephew—and it was a highlight of our weekend trip! Although I was a little sad to miss the pirate-themed sail this year, Christian made the experience unforgettable by entertaining my son and nephew with pirate stories the entire trip! 🏴‍☠️ They kept asking for me, and he was patient, and answered all of their questions. Before we even set sail, Michael went out of his way to engage the kids by teaching them how to tie knots while we waited to board—such a thoughtful touch that set the tone for a fun out we all enjoyed--adults and children alike. Highly recommend for visitors of all ages!
    icon
    Viator
    Peg T
    Jun 25
    Fabulous time on Windy Tall Ship Navy Pier! Special Thanks to Michael and Captain Ralph 👏 for the great customer service! Learned how to tie a new knot and some more of Chicago’s history. I would definitely recommend taking this cruise when visiting Navy Pier in Chicago!!
    icon
    Viator
    Steve J
    Jun 25
    We enjoyed a wonderful evening ride. The crew was helpful and attentive. The views are great and raising the sails is fun.
    Go to Evendo Review Centre
    0 / 0
    Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

    Experience a scenic sailing adventure on Lake Michigan with stunning views of the Chicago skyline aboard the Tall Ship Windy.

    Included

    • inclusion
      On-board restrooms
      Restroom on board

    Excluded

    • exclusion
      Alcoholic beverages
      Alcoholic Beverages
    • exclusion
      Snacks
      Snacks
    • exclusion
      Gratuities
      Gratuities

    Meeting Point

    Tall Ship Windy, is located near the Billy Goat Bar and Grill

    Meeting point

    600 E Grand Ave, Chicago, IL 60611 , United States

    End point

    End Point

    Tall Ship Windy, is located near the Billy Goat Bar and Grill

    Meeting point

    600 E Grand Ave, Chicago, IL 60611 , United States

    End point

    What to expect

    1

    Chicago Skyline

    You'll enjoy a quiet sail, on Tall Ship Windy, while taking in the great views of Chicago famous skyline from the lake!

    2

    Navy Pier

    Navy Pier

    Great view from the lake, and you will also board and return here.

    3

    Lake

    We will be sailing on Lake Michigan!

    The experience can be subject to change due to bad weather or unforseen circumstances. We always endeavour to give you the best possible experience.

    Additional Information

    • Additional information
      Public transportation options are available nearby
    • Additional information
      Service animals allowed
    • Additional information
      Travelers should have at least a moderate level of physical fitness
    Provided by Tall Ship Windy

    What our experts say

    • icon
      Visit Billy Goat Tavern for snacks nearby.
    • icon
      Bring a light jacket; it can be breezy.
    • icon
      Check out nearby Navy Pier after sailing.
    • icon
      Public transport makes access easy; plan ahead.
    • icon
      Consider sunset for breathtaking views.

    Why Book with Evendo?

    More About this Experience

    Introduction

    Embark on a thrilling sailing adventure with the Chicago Skyline Sail tour on Lake Michigan. Feel the wind in your hair, soak in breathtaking views, and revel in the fresh air as you cruise along the iconic Chicago skyline.

    What to expect?

    Anticipate a refreshing experience filled with awe-inspiring sights of the Chicago skyline, the vast expanse of Lake Michigan, and the invigorating feeling of sailing on a Tall Ship Windy. This tour promises a unique perspective of the city and a memorable journey on the water.

    Who is this for?

    This sailing tour is perfect for adventure seekers, nature enthusiasts, and anyone looking to escape the hustle and bustle of the city for a few hours. Whether you're a solo traveler, a couple seeking a romantic outing, or a family looking for a fun day out, this experience is suitable for all.

    Why book this?

    Immerse yourself in the beauty of Chicago's skyline from a different vantage point, gliding effortlessly on Lake Michigan. The Chicago Skyline Sail offers a fresh air experience like no other, allowing you to relax, unwind, and appreciate the city's architectural wonders in a tranquil setting.

    Good to know

    As you set sail on this adventure, remember to bring your camera to capture the stunning views. While restroom facilities are available on board, snacks and gratuities are not included, so you may want to pack some essentials for the journey. The tour's endpoint near the Billy Goat Bar and Grill makes it convenient to continue your exploration of Chicago's attractions afterward.

    Reviews

    Travelers who have experienced the Chicago Skyline Sail rave about the peaceful ambiance, friendly crew, and the unparalleled beauty of the city from the water. Many describe it as a must-do activity in Chicago, offering a unique and unforgettable perspective of the Windy City. Satisfaction is high among those who have embarked on this memorable sailing tour.

    Mobile App

    Your all‑in‑one travel companion app

    Explore expert travel guides, compare and book tours, experiences, hotels, and more—all from the palm of your hand. Download now for seamless trip planning wherever your wanderlust takes you.



    Sorry, you just missed out!

    This is a popular product and the date you are looking for just sold out. Next available date is

    Select Currency

    Choose the currency you want prices to display in.