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ON A BOAT SAILING

SIP, SAIL, & SWIM ALONG CHICAGO'S FAMOUS LAKEFRONT

ON A BOAT SAILING IS THE PREMIER PURVEYOR OF CHICAGO SAILING CHARTERS ON LAKE MICHIGAN.

Our private party bookings are perfect for birthdays, engagements, anniversaries, reunions, graduations, and more—this is luxury sailing for groups in the Windy City.

The Yacht - 2003 Jeanneau Sun Odyssey 37

S/V Dragonfly was built for day cruises & entertainment. Our 37' luxury sailboat is a fantastic venue for any special occasion. We are a fully-licensed commercial passenger vessel and operate under the highest safety standards monitored by the US Coast Guard.

Learn more about our crew and yacht here.

The Crew - Captain Greg & 1st Mate Cait

Our crew have a combined 25 years sailing experience, allowing us to curate the best possible experience for our guests. Sit back & relax as you take in the sights & sounds of Chicago's famous Lakefront.

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8 years in business. 500+ 5-star reviews. Customers love our one-of-a-kind sailing experiences.

CHICAGO SAILBOAT CHARTERS & CRUISES

FLEXIBLE AVAILABILITY - BOOK NOW!

4 Hours

USCG Captain

Chicago's famous lakefront party is back! This 4-hour private sailboat charter is designed for you & your friends to party in luxury. We will depart from Monroe Harbor, with a good mix of adventure sailing on Chicago's Lakefront along with dropping anchor at the Playpen or a private area of your choosing. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!

 $1,499 | Up to 10 Guests
 

FRI • SAT • SUN
Departing 10am & 2:30pm

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2.5 Hours

USCG Captain 

This 2.5 hour Chicago sailboat cruise will split your time us between sailing the city's famous Lakefront & eventually making our way to the famous Fireworks show at Navy Pier. These are the best seats you can possible have for a world-class fireworks show. We've all seen fireworks - you've never seen anything like this before.

$999 | Up to 7 guests 

WED 7pm SAT 8pm

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"10/10 experience - you are crazy if you DON'T book this. It was not your average crowded tour boat experience in Chicago. The dragonfly is an intimate vessel.

Laura, Grand Rapids, MI

3 Hours

USCG Captain 

This 3-hour sailboat cruise will take you & your guests on a favorable sail down the gorgeous coastline of Chicago's lakeshore, giving a unique perspective on the city's world-class architectural landscape. If you're looking for a private & intimate sailing experience- this is the cruise for you.

$999 | Up to 7 guests

WED • FRI • SAT • SUN
Departing 10am, 1:30pm & 5:00pm

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2 Hours

USCG Captain 

Relax and enjoy a captained sunset cruise on our sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off from Monroe Harbor in downtown Chicago and set sail to a favorable course on Lake Michigan. Bring your own food and drinks, listen to your favorite music, and take in the views of our city’s iconic skyline from the Lakefront.

$799 | Up to 7 guests 

FRI • SUN
Departing 6:30pm

SERVICES
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DON'T GET LEFT IN THE WAKE - BOOK NOW!

Explore world-class sailing, Great Lakes swimming & luxury amenities all summer long.

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