Historical Tours
1–2 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
from
$39
per adult
Tall Ship Windy
Tall Ship Windy
4.5
10:00 AM - 9:00 PM
Monday
10:00 AM - 7:00 PM
Tuesday
10:00 AM - 7:00 PM
Wednesday
10:00 AM - 9:00 PM
Thursday
10:00 AM - 9:00 PM
Friday
10:00 AM - 9:00 PM
Saturday
10:00 AM - 9:00 PM
Sunday
10:00 AM - 9:00 PM
Full view
About
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
Tours and Tickets by Tall Ship Windy
Romantic Tours
1–2 hours
Free cancellation
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from
$59
per adult
Architecture Tours
1–2 hours
Free cancellation
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from
$59
per adult
Historical Tours
2 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
Recommended by 92% of travelers
92% of reviewers gave this product a bubble rating of 4 or higher.
from
$89
per adult
Day Cruises
1–2 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
from
$99
per adult
Travelers talk about
(125 reviews)
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Most Recent: Reviews ordered by most recent publish date in descending order.
Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.
Popular mentions
4.5
1,541 reviews
Excellent
1,150
Very good
226
Average
78
Poor
42
Terrible
45
Chantal M
Chicago, IL75 contributions
Sep 2020
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.
Written September 6, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
jnedrud
Minneapolis, MN1 contribution
May 2022 • Family
Our family had a great time sailing with Tall Ship Windy. The day was beautiful and the wind was strong. The crew made the experience interactive for our kids, letting them help hoist the sails and steer the rudder at various points. The crew was knowledgeable and told tales of sailors gone by. It was a wonderful time.
Written June 7, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
We love our Sailor/Pirate excursions the most; so much fun and history to share! Please join us again.
Written June 13, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Kari S
Milwaukee, WI227 contributions
Aug 2022
This felt like the best choice of all boat tours in Chicago and wow, that's the truth! We did the sunset sail and it was beautiful...surreal. The Chicago skyline is amazing at sunset and the ship with the sails up was breathtaking. There is a bar on board, which was nice to have a drink while sailing.
Written August 29, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
YEAH! We are thrilled to hear how much you enjoyed your sailing charter with Tall Ship Windy!
Join us another time soon!
Written August 29, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Susan G
Lakeside Park, KY12 contributions
May 2023 • Family
Do not try to cruise with Tall Ships WIndy! I had purchased a Go City pass for my family on our vacation to Chicago. The children were very excited for the Pirate Sail but no, the young man at the ticket booth refused to accept the Go City passes. I tried several times to show the Tall Ship WIndy listing on our choice of Chicago adventures, but no, I was told I had to purchase the tickets. Too bad for the employees working the cruise. There were lots of open seats for that sail and the crew missed a hefty tip. Thank the ticket booth kid.
Written June 9, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Hello Susan, as we are not part of the Go City Pass program our ticket booth team member was not able accept their passes. We have reached out to Go City to ask them to remove us from their listing several times in the past and again after you contacted us.
Written June 14, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Barbara Mason
Chicago, IL97 contributions
Sep 2021 • Couples
Fireworks cruise - amazing BEST place ever to watch fireworks ever for me. Loved the view, be sure to ask where to sit for the best view of the fireworks, ours was superb. Close by fireworks (and not skimpy I will add!) with the city of Chicago as a backdrop, worth every penny. We had VIP tickets which I think just meant we got to get on the boat first!? First choice of seats. Fireworks show was superb and then just a short sail.
Written September 12, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Yes! We are so thrilled you had the BEST place to view the fireworks and got to get out on the lake! We always want for everyone onboard to have a superb tie and we are happy to know we did not disapoint!
Written March 12, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Allan R
16 contributions
Jun 2021 • Couples
Went on a Saturday evening tour. Get views of downtown Chicago not available anywhere else. Lovely large ship with very friendly crew. Good mix of folks onboard, we had a great time. Well worth the recommendation!
Written June 13, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Melissa M
11 contributions
Jun 2023 • Family
This was our second time riding the Windy. It did not disappoint. We took the 5 p.m. Architecture Tour and truly enjoyed the view of Chicago from Lake Michigan. We were fortunate to be allowed to help hoist the sails. This task made our tour even more special. Sailing on the Windy is a must do when visiting Chicago.
Written June 8, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
We hope you join us for a third time and may more times after that! Come back and help raise the sails anytime!
Written July 5, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Toastwitheggs
Columbia, MO117 contributions
Aug 2023 • Friends
Beautiful boat, crew was nice. Pirates, arrr. Told stories after launched. Sailed out in lake, really cool. Glad I went. I would have never gone if not for my friend booking it.
Recommend for something different to do.
Recommend for something different to do.
Written August 12, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
We are glad you joined us and hope you join us again! While I love the pirate themed sails we offer other things like our Monday night blues sail with a live band!
Written August 15, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Coloradoroadtripper
Gunnison, CO12 contributions
Despite tornado warnings for the city and counties in a 50 mile radius, despite a power outage in Chicago, despite traffic at a stand-still and warnings not to travel, Captain Bruce refused to give a refund for the trip. Shocking, irresponsible, and very disappointing,
Written June 29, 2010
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
BVnLJ
Cheswick,Pa.153 contributions
My wife and I wanted to see the Navy Pier and we discovered this very cool attraction. Once my wife seen the ship we just had to go and it did not disappoint. We took the fireworks cruise. The view of Chicago from the lake at night was awesome. We headed out at dark under diesel power then once we cleared the docks the sails went up. We did not get an opportunity to raise the sails to many volunteers. After a harbor cruse the fireworks started. It was great to see the city as a backdrop to the fireworks. The crew was excellent. I don’t know how the captain navigated the harbor with all the other boats around the man deserves a raise. We would recommend this attraction for the fireworks cruise or the pirates cruise. September 18/2009
Written October 4, 2009
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
tallgrl
Saint Louis, MO25 contributions
Going to purchase tickets for an upcoming cruise. I select the VIP option and the website gives me an option to select travel insurance. But the ticket description says that insurance is included on VIP tix? I’m guessing this is just an automatic thing but unnecessary if you go VIP?
tallgrl
Saint Louis, MO25 contributions
Thanks! I called them and spoke to Mike at the ticket booth. He confirmed if you buy VIP you don’t need to purchase the insurance add-on. Also be advised, trip insurance is only for 24 hours advance notice, although you do still get the added benefit of being able to board early too.
VeronicaOtrip
Buenos Aires, Argentina730 contributions
I would like to know if there are sails during the month of november? I am going to buy a Go Chicago Card, but it is a little bit confusing on wheter that month this tour will be available or not.
Thank you
Capt_Bruce_R
Rio Grande, Puerto Rico20 contributions
Sorry about the delay, we didn’t see the question!! Answer, we sail daily, May through Sept.
Bdbehnke
17 contributions
Hi. We bought a groupon to use for this wknd. Do I have to call to order tickets? Or can I use the groupon ordering the tickets online? I've tried calling but keep getting a recorded message. Thnaks
Capt_Bruce_R
Rio Grande, Puerto Rico20 contributions
you can make reservation online. You do not have to reserve in advance, but we do recommend it. We have 3-5 people answering phones, if we don't answer, please leave a message.
SueTravelsWithKids
Wekiva Springs, FL244 contributions
Be honest. I'm from orlando and used to 90 degree weather. If the forecast is for low 70s is it going to feel even cooler on the boat? I would be miserable if I'm cold. Or is there somewhere I could sit away from the wind. My boys are made of heartier stuff than me!
Capt_Bruce_R
Rio Grande, Puerto Rico20 contributions
question already answered.. you asked twice :)
SueTravelsWithKids
Wekiva Springs, FL244 contributions
Be honest. I'm from orlando and used to 90 degree weather. If the forecast is for low 70s is it going to feel even cooler on the boat? I would be miserable if I'm cold. Or is there somewhere I could sit away from the wind. My boys are made of heartier stuff than me!
Capt_Bruce_R
Rio Grande, Puerto Rico20 contributions
Well, yes, there is an inside area AND we provide blankets also when requested.
Bdbehnke
17 contributions
Thinking of taking our 5 year old son. But read that it's a 75 min long ride....Too long for a 5 yr old? Any thoughts or personal experiences? I know every kid is different. :)
Capt_Bruce_R
Rio Grande, Puerto Rico20 contributions
I think he will be fine, and smiling the whole time!
Nancy S
San Diego, CA13 contributions
Hi there! Can you tell me if it's a relatively smooth ride? My husband would absolutely love this, but I am pregnant and would hate to ruin the fun by leaning over the rails to be sick! Should I take a Dramamine or other motion sickness medication before hand, or would that be unnecessary? Thank you!
Capt_Bruce_R
Rio Grande, Puerto Rico20 contributions
yes, it could be considered a smooth ride... but we are a boat. We don't have many people we even complain about sickness.
Meghan M
San Francisco, CA32 contributions
Hi there!
My husband and I are headed to Chicago over Labor Day weekend (arriving Sunday and leaving Wednesday 9/7). Are there specific cruises on certain days that are not to be missed? We don't have children, and I am trying to make this memorable for my husband's birthday. Any suggestions for better days would be great!
Magda R
Lombard, IL46 contributions
go on the web side tall ship windy pick the tour you want to go see and also see the Live availability and then you will see what you want to do
Peggy O
Newburgh, Indiana10 contributions
Is the view better (architecture cruise) one one side or the other? Or does he boat travel one direction then turn around?
rfgf1
Chicago, IL9 contributions
They go out of Navy Pier and head south. Then they turn around and head back, so either side is fine. All cruising is inside the breakwater, so your always fairly close to shore.