WHAT MAKES ON A BOAT SAILING DIFFERENT
If you appreciate attention to detail, hospitality, and thoughtful amenities, this is the group experience for you! Our Chicago sailboat charters & cruises have been enjoyed by thousands of guests since 2018. As we hit the waterfront for our 7th season, we pride ourselves on offering an unforgettable way to experience Lake Michigan from the City.
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.
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.
Whether you're getting on the water for the first time or a seasoned boater, our focus is to curate your special outing with world-class sailing, comfortable amenities, and incredible views of Chicago's famous Lakefront.
2024 bookings are available from Memorial Day weekend to mid-September with multiple departures daily from centrally-located Monroe Harbor in Downtown Chicago.
Please visit our all charters page to learn more about our one-of-a-kind sailing adventures. Chicago is the best place to combine the thrill of sailing with views of a city steeped in rich architectural history - let us show you.
Cheers!
Captain Greg & First Mate Cait
OVER 500 PRIVATE CHARTERS IN CHICAGO SINCE 2018
CHICAGO SAILBOAT CHARTERS & CRUISES
LIMITED WEEKEND BOOKINGS AVAILABLE - BOOK NOW!
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!
$1,399 | Up to 7 Guests
FRI • SAT • SUN
Departing 10am & 2:30pm
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
“I rented [Dragonfly] to celebrate my bday with 6 close girlfriends. Greg was very communicative before the trip. He answered all my questions in a very timely manner. The boat is very spacious!
Dyna, Chicago, IL
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.
$899 | Up to 7 guests
WED • FRI • SAT • SUN
Departing 10am, 1:30pm & 5:00pm
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
