Planning an amazing summer for you & your friends? Anything is worth celebrating from our privately-owned 37' luxury sailboat, S/V Dragonfly.
Packed with VIP amenities & seating options for up to 10 guests, your time with On A Boat Sailing will top any brunch, baseball game, or rooftop bar in Chicago.
Summer 2024 bookings are open. Don't wait!
Chicago Sailboat
Charters & Cruises
CHECK OUT OUR CHICAGO SAILING EXPERIENCES BELOW:
Soak up the sights of our city’s iconic skyline! This 3-hour Chicago sailboat 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 landscape. If you're looking for a private & intimate way to experience Chicago - this is the cruise for you.
Starting at $899
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, anchoring the boat in the party zone. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!
Starting at $1,099
This 2.5 hour Chicago sailboat cruise will take you & your group to the closest possible viewing area for the famous Navy Pier Fireworks show. We've all seen fireworks - you've never seen anything like this before.
Starting at $799
400+ FIVE STAR REVIEWS
7 years of fresh waters, exclusive parties & unforgettable experiences.
One Boat. One Captain. One Unique Sailing Experience.
Captain Greg & First Mate Cait
We have a combined 25 years sailing experience allowing us to curate the best possible experience for our guests - it's easy because we love what we do. Expect expert boat handling, top-notch service and unforgettable vibes.
Guests:
Up to 10
Length:
37'
Private
Bathroom
Refrigerator
Access
Kitchenware
Available
S/V DRAGONFLY - 2003 JEANNEAU SUN ODYSSEY
Jeanneau is a French luxury brand of cruising class yachts made for day cruises & entertaining. Our yacht offers comfort & extra seating compared to other sailboats. The bimini in the cockpit provides shade while the dodger provides a wind break from the cool breezes on the Lake. Lounging space in the sun is available on the foredeck. Down below, the teak interior cabin has two private changing rooms, a bathroom with shower, kitchen and salon seating area.
We sail out of
Monroe Harbor
in Downtown Chicago
Browse our calendar
dates & times:
STEP ABOARD
Be first for private sailing offers & special event happenings on Chicago's famous Lakefront.