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About Tall Ship Windy
Tall Ship Windy is Chicago's Official Tall Ship! Many sailing trips daily, May - Sept rain or shine! To see current schedule online, visit our website and click "buy tickets" We have a full service bar aboard This is a fun adventure, for all ages! Open May through September
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Closed Now
Hours Today: 10:00 AM - 9:00 PM
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Tours and Tickets by Tall Ship Windy

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

Discover the Windy City your way with a Go Chicago Explorer Pass. Valid for 60 days, the pass is ideal for travelers who want to take their time exploring the city. You can visit top attractions such as the SkyDeck, Field Museum, and Lincoln Park Zoo. You also have the option to choose activities, including a sightseeing cruise or hop-on hop-off bus tour.

Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two year from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.
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60 days
from $66.00

Chicago Skyline Sailboat Cruise

Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs.
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1 hour 15 minutes
from $37.00
1321Reviews17Q&A
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BeeGirl wrote a review Sep 2020
Denver, Colorado8 contributions8 helpful votes
A fun, mellow sail along the shoreline. I liked that it was music and humor and not a lot of Chicago history bc we had already been on a tour with that info. Staff was lovely, Groupon price was awesome (don’t forget to tip!), drink prices fair.
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Date of experience: September 2020
3 Helpful votes
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Mari P wrote a review Sep 2020
Chicago, Illinois143 contributions38 helpful votes
+1
Very friendly, extremely relaxing. Very clean & highly recommended. Very scenic and relaxing way to see this beautiful city
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3 Helpful votes
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Chantal M wrote a review Sep 2020
Chicago, Illinois74 contributions27 helpful votes
We sailed Tall Ship Windy for their educational sail. It was wonderful. What a great field trip idea. We had kids from PreK to highschool. All of them were engaged and learned something new about the pirates that used to sail lake Michigan. I would highly recommend this.
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Date of experience: September 2020
1 Helpful vote
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Robert B wrote a review Aug 2020
2 contributions1 helpful vote
Had a really good time with Windy today. Beautiful weather, fair winds and a friendly captain and crew. Thanks Captain Bruce and crew
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Date of experience: August 2020
1 Helpful vote
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Shioban L wrote a review Jul 2020
1 contribution2 helpful votes
Don't support this business. We pre-booked a large party weeks in advance for my friend's husband's 35 birthday. The time came for our group to board and they only had reservations for half our party. They had an issue in their system and instead of them taking care of our group who pre-purchased and showed proof of said purchase they continued to let people board. My girlfriend was literally in tears. Totally unprofessional I would not ever book services with them.
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Date of experience: July 2020
2 Helpful votes
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