NOW BOOKING - SUMMER 2024
Chicago Lakefront Cruise
3 Hour Cruise
USCG Captain
Up to 10 Guests
Sail, swim & celebrate the natural beauty of Chicago's Lakefront. This is a relaxing & exciting three-hour sailing experience lead by a USCG-certified, expert captain.
First-time sailors love this cruise! Choose between sailing the Lakefront or dropping anchor & swimming with your crew. You won't find a better way to experience Lake Michigan from Downtown Chicago.
MEET YOUR SAILING YACHT FOR THE DAY
S/V DRAGONFLY
Guests:
Up to 10
Length:
37'
Bluetooth
Speakers
Private
Bathroom
Refrigerator
Access
Kitchenware
Available
Our 37' sailing yacht offers comfort & style compared to other sailboats. The bimini umbrella in the cockpit provides shade while the dodger windshield 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 comfortable salon seating area.
We sail out of
Monroe Harbor
in Downtown Chicago
Lakefront Cruise
dates & times:
400+ FIVE STAR REVIEWS
7 years of fresh waters, exclusive parties & unforgettable experiences.
3 Hour Cruise
USCG Captain
Up to 10 Guests
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. If you're looking for a private and intimate way to experience Chicago - this is the cruise for you.
Starting at $149pp + 6% booking fee
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
Start planning your summer sail now!
STEP ABOARD
Be first for private sailing offers & special event happenings on Chicago's famous Lakefront.