Chicago Skyline Tour: Scenic Sail on Official City Tall Ship
4.5
436 Ratings
Chicago
Experience the beauty of Chicago's skyline on a scenic sail around Lake Michigan. Discover the city's architectural wonders and enjoy breathtaking views from the Official Ship of Chicago.
Duration: 1 hour, 15 minutes
Cancellation: 1 day learn more
Highlights
  • Navy Pier - Departs from the historic Navy Pier, one of the most popular tourist attractions in the city.
  • Lake Michigan - Sail on the third-largest of the Great Lakes. Lake Michigan is itself a natural wonder.
What's Included
  • Local taxes included
What's Not Included
  • Alcoholic, Non-Alcoholic Drinks & Snacks (available for purchase)
  • Gratuities
  • Hotel pickup and drop-off
Additional Information

Escape the vigorous city life! Journey around Lake Michigan and experience the exquisite shoreline of Chicago at your own pace. Marvel at the globally renowned skyline, witness breathtaking views, and uncover the aquatic side of the Windy City. The Official Ship of the city, Windy, measuring at 148 feet in length, prides itself as one of a handful quartet-masted Schooners constructed within the United States. Recline and relish a soothing cruise aboard an authentically historical watercraft. Choose from our Pirate and Maritime Stories Sail at 1pm, Skyline/Architectural Theme Sails at 3pm and 5pm, or the Skyline Sunset Sail at 7pm.

Our sail lasts for nearly 75 minutes. The ship embarks punctually at the slated time, so we advise you to account for possible parking time, off the pier if need be.

  • All Passengers must be present 30 minutes prior to advertised sail time. The Ship leaves on time. Please allow ample time for Chicago traffic, getting lost, and not being able to park close.
  • Minimum drinking age is 21 years
  • Dress code:should be sensible for the weather
  • Children under 16 years of age, must be accompanied by an adult
  • Windy is NOT HANDICAP accessible.
  • Guests must be able to ambulate up and down 6 steps on each side of the boarding ladder.
  • Assistive devices must be left on the dockside storage area and may not be used on the ship while underway.
  • Windy is NOT HANDICAP accessible
Location
600 E Grand Ave
East Grand Avenue
We are located on the South dock, on the south side of Navy Pier, immediately in front of the Billy Goat Tavern. If walking on the south dock from the entrance, walk where you see restaurants and boats, walk pass the Ferris wheel, walk past the sign for the Shakespeare theater, then on right!
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.5
(436 Ratings)
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Tanya_s
May 26, 2024
Breathtaking - What a great experience. The lake view is breathtaking and I even helped hoist the main sail! The crew was super friendly too. 2
Review provided by Viator
Becky_b
May 24, 2024
Highly recommend - The crew was wonderful and the experience was better than expected. I will definitely recommend this to friends and would do it again.
Review provided by Viator
Whitney_t
May 20, 2024
10/10 - Loved this experience! Guide was super fun and funny with some good facts too. Beautiful ship and views!
Review provided by Viator
Alla_g
May 20, 2024
Fantastic - It was amazing. We were with 3 kids and 2 adults, it was fantastic. Small tall ship it was like authentic trip. Thank you all team so much . The weather , beautiful buildings and the lake were amazing for taking pictures as well.
Review provided by Viator
Coloneledmunds
Sep 29, 2023
The Wonderful Windy! - Wow...great trip with fantastic narration. Calming, relaxing, and an excellent bar too! Book a trip on the Windy you will love it@
Review provided by Tripadvisor
David_f
Sep 26, 2023
Wonderful evening. - The views were spectacular!! The crew was very knowledgeable and friendly. We are already talking about doing it again next year.
Review provided by Viator
Nevillethehero
Sep 24, 2023
Most fun tour in Chicago - The most fun tour we’ve had of Chicago. The crew is fantastic, and the tour guide is hilarious. His sense of humor really sets this tour apart from the rest, while still offering interesting insights on the city’s unique skyline. Loved it.
Review provided by Tripadvisor
Sharon_m
May 28, 2024
Evening cruise - Nice cruise, disappointed they could not use the sails. Remember to take a jacket, it can get windy.
Review provided by Viator
J4827mfvanessaf
Oct 2, 2023
Ahoy matey - Family friendly and super fun to do. Staff are very good entertainers and fun to participate on their acts. Knowledgeable about the city so you get to learn a little history about Chicago SkiyLine and the City. I thought the tour was going through the canal but it actually goes alongside the lake which was fun to fell the breeze like if you would be at open sea. Is a fun adventure to do while in the city. If you are lucky you get to take pictures with the captain too :D
Review provided by Tripadvisor
Brandy_h
May 28, 2024
Very disappointed - Tour being unreasonable and unresponsive to rescheduling tour time. I called and emailed and was still unsuccessful in my request.
Review provided by Viator
Select Date and Tickets
up to 15 guests
1 Adult
June 2024
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