Chicago 
Classic Handmade Pasta 
Aerial Basics
Chicago Rivers, Parks, and Architecture Tour
River Architecture Tour (Michigan Ave)
River Architecture Tour (Navy Pier)
Classic Lake Tours
Little India Food Tour
Chinatown Food and Culture Tour
Badass Bitches Tour
Conquering the Restaurant Wine List
Drunk Shakespeare - Balcony Seats
Drunk Shakespeare - Stage-Side Seats
Blue Man Group
Architecture Fireworks Tours (Navy Pier)
Fireworks Sail
Mixed Martial Arts (River North)
Mixed Martial Arts Intro
NRA Basic Shotgun Shooting CourseChicago Skyline Cruise
What to expect
- Enjoy Chicago's beautiful skyline from a unique vantage point
- Take a leisurely trip around Lake Michigan on a sailboat
- Relax with the wind at your back and gentle waves rocking you back and forth
Booking Calendar
| Date | Start Time | Duration | # Spots | Price |
|---|---|---|---|---|
| Wed, Jun 19 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Jun 20 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Jun 20 | 9:00pm | 75 min | 0 | $37.00 |
| Fri, Jun 21 | 7:00pm | 75 min | 10+ | $37.00 |
| Fri, Jun 21 | 9:00pm | 75 min | 10+ | $37.00 |
| Sat, Jun 22 | 7:00pm | 75 min | 10+ | $37.00 |
| Mon, Jun 24 | 7:00pm | 75 min | 10+ | $37.00 |
| Tue, Jun 25 | 7:00pm | 75 min | 10+ | $37.00 |
| Wed, Jun 26 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Jun 27 | 7:00pm | 75 min | 0 | $37.00 |
| Thu, Jun 27 | 9:00pm | 75 min | 0 | $37.00 |
| Fri, Jun 28 | 7:00pm | 75 min | 10+ | $37.00 |
| Fri, Jun 28 | 9:00pm | 75 min | 0 | $37.00 |
| Sat, Jun 29 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Jun 30 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Jun 30 | 9:00pm | 75 min | 0 | $37.00 |
| Mon, Jul 1 | 7:00pm | 75 min | 10+ | $37.00 |
| Tue, Jul 2 | 7:00pm | 75 min | 10+ | $37.00 |
| Wed, Jul 3 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Jul 4 | 7:00pm | 75 min | 10+ | $37.00 |
| Fri, Jul 5 | 7:00pm | 75 min | 10+ | $37.00 |
| Fri, Jul 5 | 9:00pm | 75 min | 10+ | $37.00 |
| Sat, Jul 6 | 7:00pm | 75 min | 10+ | $37.00 |
| Mon, Jul 8 | 7:00pm | 75 min | 10+ | $37.00 |
| Tue, Jul 9 | 7:00pm | 75 min | 10+ | $37.00 |
| Wed, Jul 10 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Jul 11 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Jul 11 | 9:00pm | 75 min | 10+ | $37.00 |
| Fri, Jul 12 | 7:00pm | 75 min | 10+ | $37.00 |
| Fri, Jul 12 | 9:00pm | 75 min | 10+ | $37.00 |
| Sat, Jul 13 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Jul 14 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Jul 14 | 9:00pm | 75 min | 10+ | $37.00 |
| Mon, Jul 15 | 7:00pm | 75 min | 10+ | $37.00 |
| Tue, Jul 16 | 7:00pm | 75 min | 10+ | $37.00 |
| Wed, Jul 17 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Jul 18 | 7:00pm | 75 min | 0 | $37.00 |
| Thu, Jul 18 | 9:00pm | 75 min | 0 | $37.00 |
| Fri, Jul 19 | 7:00pm | 75 min | 10+ | $37.00 |
| Fri, Jul 19 | 9:00pm | 75 min | 10+ | $37.00 |
| Sat, Jul 20 | 7:00pm | 75 min | 10+ | $37.00 |
| Mon, Jul 22 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Aug 1 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Aug 1 | 9:00pm | 75 min | 10+ | $37.00 |
| Fri, Aug 2 | 7:00pm | 75 min | 10+ | $37.00 |
| Fri, Aug 2 | 9:00pm | 75 min | 10+ | $37.00 |
| Sat, Aug 3 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Aug 4 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Aug 4 | 9:00pm | 75 min | 10+ | $37.00 |
| Mon, Aug 5 | 7:00pm | 75 min | 10+ | $37.00 |
| Tue, Aug 6 | 7:00pm | 75 min | 10+ | $37.00 |
| Wed, Aug 7 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Aug 8 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Aug 8 | 9:00pm | 75 min | 10+ | $37.00 |
| Fri, Aug 9 | 7:00pm | 75 min | 10+ | $37.00 |
| Fri, Aug 9 | 9:00pm | 75 min | 10+ | $37.00 |
| Sat, Aug 10 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Aug 11 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Aug 11 | 9:00pm | 75 min | 10+ | $37.00 |
| Mon, Aug 12 | 7:00pm | 75 min | 10+ | $37.00 |
| Tue, Aug 13 | 7:00pm | 75 min | 10+ | $37.00 |
| Wed, Aug 14 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Aug 15 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Aug 15 | 9:00pm | 75 min | 10+ | $37.00 |
| Fri, Aug 16 | 7:00pm | 75 min | 10+ | $37.00 |
| Fri, Aug 16 | 9:00pm | 75 min | 10+ | $37.00 |
| Sat, Aug 17 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Aug 18 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Aug 18 | 9:00pm | 75 min | 10+ | $37.00 |
| Mon, Aug 19 | 7:00pm | 75 min | 10+ | $37.00 |
| Tue, Aug 20 | 7:00pm | 75 min | 10+ | $37.00 |
| Wed, Aug 21 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Aug 22 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Aug 22 | 9:00pm | 75 min | 10+ | $37.00 |
| Fri, Aug 23 | 7:00pm | 75 min | 10+ | $37.00 |
| Fri, Aug 23 | 9:00pm | 75 min | 10+ | $37.00 |
| Sat, Aug 24 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Aug 25 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Aug 25 | 9:00pm | 75 min | 10+ | $37.00 |
| Mon, Aug 26 | 7:00pm | 75 min | 10+ | $37.00 |
| Tue, Aug 27 | 7:00pm | 75 min | 10+ | $37.00 |
| Wed, Aug 28 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Aug 29 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Aug 29 | 9:00pm | 75 min | 10+ | $37.00 |
| Fri, Aug 30 | 7:00pm | 75 min | 10+ | $37.00 |
| Fri, Aug 30 | 9:00pm | 75 min | 10+ | $37.00 |
| Sat, Aug 31 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Sep 1 | 7:00pm | 75 min | 10+ | $37.00 |
| Sun, Sep 1 | 9:00pm | 75 min | 10+ | $37.00 |
| Mon, Sep 2 | 5:00pm | 75 min | 10+ | $37.00 |
| Mon, Sep 2 | 7:00pm | 75 min | 10+ | $37.00 |
| Thu, Sep 5 | 5:00pm | 75 min | 10+ | $37.00 |
| Fri, Sep 6 | 5:00pm | 75 min | 10+ | $37.00 |
| Fri, Sep 6 | 7:00pm | 75 min | 10+ | $37.00 |
| Sat, Sep 7 | 11:00am | 75 min | 10+ | $37.00 |
| Sat, Sep 7 | 5:00pm | 75 min | 10+ | $37.00 |
| Sat, Sep 7 | 7:00pm | 75 min | 10+ | $37.00 |
| Mon, Sep 9 | 5:00pm | 75 min | 10+ | $37.00 |
| Tue, Sep 10 | 5:00pm | 75 min | 10+ | $37.00 |
| Wed, Sep 11 | 5:00pm | 75 min | 10+ | $37.00 |
| Thu, Sep 12 | 5:00pm | 75 min | 10+ | $37.00 |
| Fri, Sep 13 | 5:00pm | 75 min | 10+ | $37.00 |
| Fri, Sep 13 | 7:00pm | 75 min | 10+ | $37.00 |
| Sat, Sep 14 | 11:00am | 75 min | 10+ | $37.00 |
| Sat, Sep 14 | 5:00pm | 75 min | 10+ | $37.00 |
| Sat, Sep 14 | 7:00pm | 75 min | 10+ | $37.00 |
| Mon, Sep 16 | 5:00pm | 75 min | 10+ | $37.00 |
Ready to Book?
Select a time slot first! (212) 858 9559About this Activity
Key Highlights
| Price | $37.00 per guest |
| Duration / Session | 75 min |
| # Sessions | 1 |
| Rating | 27 positive reviews |
Cancellation Policy
Reviews
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Charles C.
Chicago Skyline Cruise September 19, 2017Great staff and perfect amount of time. No scams anything additional was totally up to you
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Abigail J.
Chicago Skyline Cruise September 2, 2017Really relaxing to be on the water, and some fun pirate storytime with Zach. Thanks for a great time!
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Tony S.
Chicago Skyline Cruise August 21, 2017Great staff! Very nice short cruise for a scenic view of our City!!
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Marion B.
Chicago Skyline Cruise August 12, 2017the sunset cruise was stunning, talented friendly staff, a very capable captain. we left the pier, raised the sails and had a delightful sail looking at the Chicago skyline, bartender was great he made mermaid drinks, that were a rum coconut pineapple concoction, extremely tasty. Just a wonderful adventure and very reasonably priced.
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Marina G.
Chicago Skyline Cruise August 10, 2017Pirate Horns did an amazing job telling pirate stories with jokes for adults as well as the kids. He really made this experience memorable! Kids loved the ship, pulling the sails, and the beautiful Chicago scenery.
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BiggJoeb .
Chicago Skyline Cruise August 10, 2017Great experience on the boat..cant believe iv never gotten on this before...30 bucks a person for 75 min on the lake I suggest going on the 9 o'clock trip better pics guaranteed . It's a hands on experience all the way...bar downstairs. Will definitely be back
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Lori K.
Chicago Skyline Cruise August 4, 2017A nice relaxing trip. This is a fun activity for any age. We did the pirate cruise but they offer other themed trips. You set sail from the docks at Navy Pier. You can get some beautiful pictures of the coastline while enjoying a tasty beverage on the water. Buy a drink/snack card at the ticket booth. You'll save a few dollars. You can help hoist the sails, listen to true pirate tales and if you ask nicely the captain will let you take the ships wheel for a quick pic. I suggest getting a seat on the foredeck (front) if possible and if you want a drink get it as soon as you get on otherwise you'll wait in line for a bit. It would have been nice if the pirate stories were told over the speakers instead of just on the main deck. Overall a great way to spend some time on the water away from the busy city.
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Grace C.
Chicago Skyline Cruise July 8, 2017This is was a BLASTTTTT!!! Other story about the pirates in Chicago were much more interesting than expected. I learned a lot about the history. I would honestly do it again just because it was funny and informative. Great for kids and adults. They have a bar!!! Win!!
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Tracy M.
Chicago Skyline Cruise July 7, 2017Wonderful serene trip on the lake, we enjoyed every moment as well the beautiful skyline and the ability to see three states...
Great way to see the sunset over the Chicago Skyline -
Carol M.
Chicago Skyline Cruise June 19, 2017This was a great tour. We took my grandfather for fathers day and he was just having a blast. I would suggest you buy a drink ticket in advance since you can save $2 that way and also the drinks are pretty fairly priced, usually I am used to paying $4 when I go to the zoo and want a gatorade, here on the boat it was only $2, which was great since it was a warm day. It was pretty cool to be on a sailboat and the tour provided some great information that I didn't even know about my own city! Kids would also love it!
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Jessica D.
Chicago Skyline Cruise September 2, 2016Was able to order 10 tickets without any issues. Aug 31st, was the last firework show of Navy Piers season. Was very excited they still had availability. Being a full working wooden ship we could feel the "chopy waters". We where invited to help raise the sails! Since they are interactive and a teaching vessel.
Beautiful views, fun & funny crew. Very willing to work with us for pictures and making our experience fantastic!
They are very reasonable priced tickets! Worth every penny! -
Ian S.
A Sailor's Life for Me! Tall Ship Experience September 13, 2015Loved it!
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Galen G.
Real Pirates of Lake Michigan Tour October 6, 2013Rick was an amazing storyteller, glad we picked the Real Pirate cruise, probably the best experience I've had on Navy Pier, I felt like I actually learned something about the Great Lakes history. Tell your friends!
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alfie2u .
Real Pirates of Lake Michigan Tour September 6, 2013The cruise was great. When I got there I found that there were three different places that you can sit. The front end, the middle and the back end. If you want to sit on the ends make sure that you are in the front of the line and quickly make your way to either end. Those seats fill up fast. The middle is a good place to sit as that is where the shows and presentations are taking place. On our cruise our pirate had different items and told us how they were used by pirates back in the day. Next at the beginning of the cruise they will ask for volunteers and that is to help raise the sails. If interested get up and do it. It looked like fun. After the sails were up and we were away from Navy Pier the engines were turned off and we were sailing with the wind. It was very quiet and relaxing. We had great views of the Chicago. Eventually we made it back to Navy Pier. It was a very nice and relaxing ride. Finally, if you have kids bring them along as the crew and our pirate host was great with them. From what I saw we all (kids and adults) had a lot of fun
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LaurLaw .
Chicago Skyline Cruise August 12, 2013What a great program to be able to sail on a tall ship and experience the views of the Chicago skyline. I was fortunate enough to be onboard for the fireworks and I feel like we had the best seats in the house. There is a bar available with drink purchases and the entire crew is enthusiastic. The Captain is friendly and available for questions. Highly recommend.
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Starfish738 .
Real Pirates of Lake Michigan Tour July 31, 2013I just got back from my first trip ever to Chicago. I took my 17 year old daughter and while we did several fun things, The Tall Windy pirate ride with Pitate Rick was at the top. I was enthralled with each of his true pirate stories. I loved his passion for the stories and his delivery made it all so much fun.
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Jae H.
Lakeside Architecture Sail July 25, 2013I'd like to start off my saying that tall ship windy is perfect for people with children. Not only does it offer the classic architecture tour, it also offers themed events. The name of the tour I went on was something like "real pirates". An employee dressed up like a pirate told stories on the main deck. People not interested on the stories were able to go onto one of the upper decks to relax.
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Melissa S.
Real Pirates of Lake Michigan Tour July 14, 2013Our whole family had a wonderful experience with tall ship windy. We took the pirate excursion and pirate Rick was phenomenal. He was entertaining, informative and fun for adults and kids alike. My husband and I along with our 7 and 4 year old alike had a lovely afternoon. He even "coded" information so the adults understood but kids were not impacted by violent pirate imagery. Perfect! We even bought the touristy photo at the end as a memento. We will definitely sail again with tall ships windy:)
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Ashley C.
Chicago Skyline Cruise June 27, 2013We sailed on the Windy today and had a fabulous time! The entire crew were amazing and really catered to the kids on the ship showing them sailing skills and allowing them to participate.
The views of the city skyline were beautiful and the ship was clean and safe. I highly recommend this trip if you are visiting or a local! -
Sandra L.
Real Pirates of Lake Michigan Tour June 21, 2013Took a Pirate cruise on the Tall ship Windy yesterday. We had a great time! Pirate Dave was very into his role and job. He was entertaining and also full of facts about life on the high seas of Lake Michigan. A bar was also on board,limited,but a nice perk and also a"head" if you needed that. The ship was smooth sailing and they even offered us blankets to ward off the lake chill. The crew was very gracious and friendly. They even gave us back our tickets to use at a later date for a half price cruise. It was a beautiful,sunny day and had great views of the city and the lake itself. I would recommend this tour to vacationers and Chicagoans like me!
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Sandy G.
Real Pirates of Lake Michigan Tour June 14, 2013I took my 9 yr old niece on the pirate sailing. We both had a great time. The boat left on time and the Crew were professional and endured all had a great and safe time. They made sure all the children were included in the pirate takes and actually had the kids act out scenes. Great outing on a sailboat with beautiful Chicago views.
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Donna J.
Lakeside Architecture Sail October 2, 2012Loved being on a tall ship. Even got to hoist the sails. It was a beautiful September day so there was plenty of wind. Loved seeing the city from the Lake. Tour guide was great but I'm glad I did the architectural boat tour first. It wasn't always easy to know which building was which.
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Susan F.
Real Pirates of Lake Michigan Tour October 1, 2012Went on the Friday night Pirate cruise. Being a local, wasn't expecting much at Navy Pier. Had a beer at Billy Goat instead of waiting in line. Was entertained by the stories of the Great Lakes pirates and a couple beers. A little chilly, but they provided blankets. Overall, a good way to start out the weekend!
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Chris A.
Real Pirates of Lake Michigan Tour October 2, 2018Did not leave comment
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Teri B.
Chicago Skyline Cruise September 4, 2017Did not leave comment
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Alexander B.
Real Pirates of Lake Michigan Tour June 2, 2017Did not leave comment
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Quittman F.
Lakeside Architecture Sail August 23, 2015Did not leave comment
