top of page

ON A BOAT SAILING

PRIVATE SAILBOAT CHARTERS IN CHICAGO

SERVICES

YOUR CHICAGO SAILING EXPERIENCE STARTS HERE
CHOOSE FROM CHARTERS & CRUISES BELOW:
 

ABOUT ON A BOAT SAILING

We're a one boat, one captain business sharing our passion for sailing from the docks of Monroe Harbor in Downtown Chicago. Our trips have been enjoyed by thousands of guests since our first private charter in 2017. As we enter our 7th season, we pride ourselves on offering a safe & unforgettable experience on Lake Michigan for you & your group.

Our Crew - Captain Greg & 1st Mate Cait

We have a combined 25 years sailing experience allowing us to curate the best possible experience for our guests. Sit back & relax with expert boat handling, top-notch service & care-free times on Chicago's famous lakefront.

2003 Jeanneau Sun Odyssey 37

S/V Dragonfly was built for day cruises & entertaining, our 37' luxury sailboat is a favorable choice among enthusiasts. We are a fully-licensed commercial passenger vessel and operate under the highest safety standards monitored by the US Coast Guard.

 400+ FIVE-STAR REVIEWS
bottom of page
Book Now