FROM $799 FOR UP TO 6 GUESTS
Private Sailboat Charters & Cruises in Chicago
WED • FRI • SAT • SUN
MULTIPLE DEPARTURES DAILY
Whether you're cruising the city skyline, partying hard at the playpen or taking in the Navy Pier fireworks from the best seats in the house - you won't forget the time you sailed Lake Michigan aboard our 37' luxury sailboat!
OVER 500 PRIVATE CHARTERS IN CHICAGO SINCE 2018
OUR CHARTERS & CRUISES
Starting price includes up to 6 guests. Custom pricing for additional guests up to 10 during checkout.
Click 'book now' button on any product below to browse dates, times, FAQs, and more. Our aim is to make the process from booking to sailing as seamless as possible. Reach out if you have any questions!
This 3-hour Chicago 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 way to experience Chicago - this is the cruise for you.
Starting at $899
WED • FRI • SAT • SUN
10AM, 1:30PM & 5:30PM DAILY
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.
Starting at $799
FRI • SUN
6:30PM DAILY
Chicago's famous lakefront party is back. This 4-hour chicago sailboat charter is designed for you & your friends to party in luxury - where ever you choose! We will depart from Monroe Harbor, sailing Chicago's lakeshore to begin your voyage. On nice days, you & your guests can drop anchor to swim & float anywhere on the Lakefront. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!
Starting at $1,099
FRI • SAT • SUN
10AM & 2:30PM DAILY
This 2.5 hour Chicago sailboat rental 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.
Starting at $899
7PM WEDNESDAY'S
8PM SATURDAY'S
WHAT MAKES ON A BOAT SAILING DIFFERENT
We're a one boat, one captain small family business sharing our passion for sailing with our customers. Our boat, S/V Dragonfly, has played host to thousands of guests since our first private sailing charter in 2018.
Unparalleled Sailing Expertise
Captain Greg Scannell and First Mate Cait Scannell share a combined 25 years of sailing experience, including an 8-month, 5,500 nautical mile voyage from Chicago to the Bahamas and back in 2021.
400+ private charters later, we're actively curating the best experiences for our guests looking to explore the joys of sailing on Lake Michigan. Let us show you!
Luxury & Comfort Aboard S/V Dragonfly
Our 37' sailing yacht was designed for entertaining & comfort. Guests love the flexibility of luxury sailing along with dropping anchor & swimming or floating with a cold one, should the weather permit.
Bluetooth connectivity to play your own music, onboard bathroom facilities, and ample space above and below deck makes stepping aboard Dragonfly for the day an absolute breeze.
“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