This 3-hour sailing adventure departs 3x/daily from
Monroe Harbor in Downtown Chicago.
Soak up the sights of our city’s iconic skyline! Our crew 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 wonders.
312.619.7858
call us for exclusive pricing & fee-free booking
OVER 500 PRIVATE CHARTERS IN CHICAGO SINCE 2018
YOUR VIP SAILING EXPERIENCE AWAITS YOU.
Guests:
Up to 7
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.
CRUISE THE LAKEFRONT IN STYLE & COMFORT
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 for 7 guests
• BYOB or add a drink package now
WED • FRI • SAT • SUN
10AM, 1:30PM & 5PM DAILY
Flexible Booking Features
50% Deposit, Fully-Refundable
We recognize 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
