Chicago Skyline Sunset Sail Aboard Official Flagship of Chicago 148' S/V Windy

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From $49.00

2 reviews   (5.00)

Price varies by group size

Lowest Price Guarantee

Pricing Info: Per Person

Duration: 1 hours

Departs: Chicago, Chicago

Ticket Type: Mobile or paper ticket accepted

Free cancellation

Up to 24 hours in advance.

Learn more


The famous Tall Ship Windy sunset sail is truly famous. Used in many world-reknown photos, backdrops for special events, weddings, or just an evening out, the sunset sail aboard one of the only four-mast Schooners still in operation will not disappoint. You will enjoy a sail on Lake Michigan and at just the right moment, S/V Windy will gently turn toward the Chicago skyline for a view of our spectacular sunset. Sit back and relax, enjoy some soothing music, and gently complete your day with this dramatic sunset.

What's Included

GST (Goods and Services Tax)

Landing and facility fees

Restroom on board

WiFi on board

What's Not Included

Alcoholic Beverages



Traveler Information

  • CHILD: Age: 0 - 12
  • ADULT: Age: 13 - 120

Additional Info

  • Gear/equipment sanitised between use
  • Hand sanitiser available to travellers and staff
  • Paid stay-at-home policy for staff with symptoms
  • Regularly sanitised high-traffic areas
  • Suitable for all physical fitness levels
  • Contactless payments for gratuities and add-ons
  • Guides required to regularly wash hands
  • Infants are required to sit on an adult’s lap
  • Public transportation options are available nearby
  • Service animals allowed

Cancellation Policy

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

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

What To Expect

Navy Pier
148' Tall Ship Windy departs from historic Navy Pier, the entertainment venue in Chicago

10 minutes • Admission Ticket Free

Lake Michigan
Tall Ship Windy will sail from Navy Pier into Lake Michigan and at the perfect time, turn so our guests may see the glorious sunset behind the Chicago Skyline.

50 minutes • Admission Ticket Included

Chicago Skyline
As you sail on Tall Ship Windy, guests will have a phenomenal view of the Chicago Skyline.

15 minutes • Admission Ticket Included

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