sailboat in chicago

Join Us Next Season for More Sailing Fun Starting Mid-May 2025

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Chicago Skyline Sail Aboard 148' Tall Ship Windy

Quick details.

Hour Glass Duration: 75 Minutes
User Ages: All Ages
Calendar Availability: Daily
Sailboat Sail: Skyline Cruise Chicago
Map Marker Departure: Chicago's Navy Pier

General Admission Boarding

Vip captains boarding.

Experience breathtaking views of Chicago from the waters of Lake Michigan! Leave the hustle and bustle behind and explore Chicago’s gorgeous shores and skyline with a leisurely trip around Lake Michigan.

There’s no better place to view Chicago or Lake Michigan than aboard 148′ S/V Windy; the Official Tall Ship Ambassador for the City of Chicago. Don’t miss these scenic and educational cruises from Chicago’s famous traditional tall ship! Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tours at 3pm and 5pm and Sunset and Skyline Sails at 7pm.

Experience The Beautiful Chicago Lakefront With Three Sailing Options

Tall Ship Windy offers three exciting ways to enjoy the Chicago lakefront and skyline. Learn more about our Skyline sails and book today!

1pm. Pirates and Maritime Stories

Join us on our main deck for “True Stories of Piracy” on the Great Lakes and the Caribbean! From epic battles to trickery and treasure, experience the incredible tales of real pirate adventure that happened right here on these magnificent inland seas. This Chicago sail is both educational and entertaining!

On this unforgettable sail, you will also enjoy awe-inspiring views of the world-famous skyline of the Windy City while sailing the gentle waters of Lake Michigan. There’s something for everyone on this fun tour.

Participants and guides on an educational sailing tour in Chicago

3pm & 5pm. Architecture and Skyline Sails

Experience breathtaking views of Chicago from the water! Leave the hustle and bustle behind and explore Chicago’s gorgeous shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the water. The 3pm and 5pm tours feature the history of Chicago and its world-famous architecture. To learn about the people, plans and persistence that shaped Chicago’s most famous sights join us on the main deck and enjoy the lively and educational narration.

5PM: Happy Arr-our Chicago Skyline Sail

Enjoy onboard happy hour drink specials every night at 5pm! All ages welcome. Happy hour specials for guests 21+, with valid ID.

Chevron down Beginning September 3: Enjoy a Sunset Skyline Sail at 5pm and a Late Summer Twilight Sail at 7pm

Our sailing schedule changes with the season. Beginning September 3, enjoy a Sunset Skyline sail at 5pm and a Late Summer Twilight Sail at 7pm.

7pm. Sunset and Skyline Sail

Head out on our traditional tall ship and explore the majesty of Lake Michigan while Windy sails across our beautiful lakefront Chicago skyline. From the world-famous Tall Ship Windy, experience the phenomenal sun setting across the Chicago Skyline. A perfect Sunset Skyline Sail for individuals, family and friends.

On our Twilight Sail, enjoy the beautiful colors splashed across the post-sunset sky. You’ll enjoy an evening sail on Lake Michigan aboard Tall Ship Windy and take in the world-famous Chicago skyline as day transitions to night.

Chevron down Board First with VIP Captains Boarding - Limited Tickets Available!

All seating on board Tall Ship Windy is first come, first served. Guests with VIP Captains Boarding tickets board first before General Admission ticket holders. A limited number of VIP tickets are available and are likely to sell out. Board first to choose your seat on one of Windy’s three decks: the forward, middle or aft.

All VIP Captains Boarding tickets also include trip insurance. Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.

Chevron down Add-on Trip Insurance

$8.00 Per Guest | Add to your ticket at checkout

Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. Refunds for cancelled charters are less the $8.00 cost of insurance and 3% booking fees.

General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.

Chevron down Cancellation Policy
RAIN OR SHINE EVENT: In the unlikely event that your tour is cancelled, you may exchange your ticket for another day or receive a refund.
No-shows will not be eligible for rescheduling or refund. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture.
The Captain reserves the right to postpone a sail for up to 15 minutes in the case of passing inclement weather.
Add-on Trip Insurance: Allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time.

Become a Skyline Sails Member!

Related sails.

Hour Glass 90 Minutes

Fireworks Cruise From Navy Pier Aboard Tall Ship Windy!

Watching fireworks from Navy Pier has become a Chicago tradition and there is no better seat in the house to watch the show than sailing aboard 148′ Tall Ship Windy – the Official Flagship of the City of Chicago! Order a cold drink from our bar and enjoy a thrilling fireworks performance as you sail along the stunning and iconic Chicago skyline during this special event sail.

Great for Children!

Educational Sail: Tall Ship Discovery Sail

History comes alive on this exciting Windy City boat tour. Enjoy an educational adventure for curious minds of all ages with the backdrop of the iconic Chicago skyline always in view. Led by our crew-educators, experience a hands-on sailing excursion in Chicago aboard Windy.

Choose Windy City Sailing for your Chicago Sailboat Charter

charter yacht on lake Michigan sailing with windy city sailing

View All Private Yacht Charters

LUXURY ACCOMODATIONS

Our sailing yachts accommodate 1 to 10 people. We offer charters with captain and crew for groups up to six (6) or a bareboat charter for groups up to ten (10) with a USCG Licensed Captain paid separately. With up-to-date amenities and two bathrooms onboard, we assure the comfort of all our guests.

CUSTOMIZED CHICAGO SAILING CRUISES

All private Chicago sailboat charters depart and return according to your schedule. All Chicago sailboat cruises have three-hour minimums. Charter extensions are available upon request. Yes, we encourage you to bring food and refreshments, including alcoholic beverages.

Our yachts are professionally maintained and equipped. In addition, we certify, train and employ United States Coast Guard Captains with over 20 years of experience. Because of this, rest assured that you are in excellent hands. Also, all of our captains are enrolled in USCG mandated drug screening programs.

CONVENIENCE

The yachts are at the North End of Belmont Harbor, just east of Wrigley Field—or 15 minutes from the Chicago Downtown area. Windy City Sailing is easily accessible via Uber, Lyft, taxis, and bicycles. Also, parking is available via the City of Chicago. Gift certificates are available for all Chicago sailboat cruises and bareboat charters. We confirm reservations with a 50% deposit, fully refundable with a seven-day notice. Gratuity is at your discretion (we recommend 20% to our outstanding crew).

SPECIAL EVENT YACHT CHARTERS

Fireworks over Chicago view from Lake Michigan

4th of July Sailing Charter

Each year, the Fourth of July Sailing Charter gives the citizens of Chicago the chance to witness some of the nation's most spectacular firework displays from the comfort of a boat. The tour has become increasingly popular and is one of the highest rated Independence Day activities.

Chicago Air Show Charter

Chicago Air and Water Show is a remarkable event that has long been captivating city dwellers. By taking a sailboat charter from us, you can experience the show from the lakefront. You won't need to fight the crowds for the best view, as you will be luxuriating on your yacht with an unparalleled outlook of the show.

Navy Pier Firework Charter

During summer, the Navy Pier gives us breathtaking firework shows. For an unforgettable experience, there is no better way to appreciate these amazing visuals than to charter a yacht . Our dedicated captains and crew members make sure that all your needs are taken care of, so you don’t have to worry about anything else. With our exclusive amenities, it is not even worth considering any other way to view these displays.

Book Your Chicago Sailing Trip Now

WITH WINDY CITY SAILING

We know you will have questions about sailing charters, so feel free to reach out via phone or email.

Please contact Edwina at 773.868.0096 or [email protected] for details and pricing.

Frequently Asked Questions

Have you ever wanted to sail but were unsure what it would cost to charter a private yacht? If so, Windy City Sailing is here to help with all your sailing–related questions. We have made things easy to find by categorizing our questions, and if there’s anything you can’t find, feel free to reach out. Our knowledgeable staff is here to answer all your questions about sailing along the wonderful Chicago Lakeside. From planning the perfect corporate outing for out-of-town guests to helping you witness the incredible 4th of July fireworks , we have it all covered!

Review our FAQ