Soak up the sights of our city’s iconic skyline! This 3-hour cruise will take you & your guests on a favorable sail from Monroe Harbor down the gorgeous coastline of Chicago's lakeshore, giving a unique perspective on the city's world-class architectural wonders.
OVER 500 PRIVATE CHARTERS IN CHICAGO SINCE 2018
ONE BOAT. ONE CAPTAIN. ONE UNIQUE EXPERIENCE.
Guests:
Up to 10
Length:
37'
Bluetooth
Speakers
Private
Bathroom
Refrigerator
Access
Kitchenware
Available
S/V Dragonfly offers world-class sailing with comfortable amenities, encouraging you & your guests to focus on the adventurous day ahead.
The bimini umbrella in the cockpit gives ample shade and some light rain protection in our main seating area. Willing guests are welcome to relieve our captain and try their hand at the helm!
Lounging space for sunbathing and lake-gazing is available on the foredeck. This will be a popular locale for photo opportunities on beautiful days! Those camera rolls are no match for these views.
Down below, the teak interior cabin has two private changing rooms, a bathroom with shower, kitchen and comfortable salon seating area. The perfect place to store your bags, keep your drinks cool and prepare the days provisions.
400+ FIVE STAR REVIEWS
7 years of fresh waters, exclusive parties & unforgettable experiences.
ANY CELEBRATION IS MORE MEMORABLE FROM OUR 37' LUXURY SAILBOAT!
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. First time sailors will be amazed at the difference between sailing and other boating activities. It's one-of-a-kind!
Starting at $899
WED • FRI • SAT • SUN
10AM, 1:30PM & 5:30PM DAILY
Flexible Booking Plan - 50% Deposit, Fully-Refundable
We recognize that plans change, so we've designed our booking options to be incredibly flexible. This ensures you have the freedom to make adjustments with ease, providing peace of mind for your experience with On A Boat Sailing.
100% Refund up to Two Weeks From Departure
50% Refund up to 48 Hours From Departure
Full Refund for Weather Related Cancellations
Swap Dates With No Fees-Subject to Availability
STEP ABOARD
Be first for private sailing offers & special event happenings on Chicago's famous Lakefront.