Set sail on a luxurious Chicago lakefront cruise and enjoy breathtaking city views from the water. Whether relaxing, swimming, or sightseeing, this private boat experience offers a unique perspective of the Windy City.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
3 hours
Fitness Level
Suitable for most fitness levels, no prior experience needed
Wildlife
History
The Chicago Lakefront has been a vital part of the city's development since the 19th century, serving as a hub for recreation and transportation.
Conservation
The cruise operators participate in local water conservation efforts and promote eco-friendly practices to protect Lake Michigan’s ecosystem.
On A Boat Sailing
Set sail on a luxurious Chicago lakefront cruise and enjoy breathtaking city views from the water. Whether relaxing, swimming, or sightseeing, this private boat experience offers a unique perspective of the Windy City.
On A Boat Sailing is a Chicago-based private charter company offering curated sailing and yachting experiences on Lake Michigan.
The company specializes in a range of private cruises including skyline sunset sails, lakefront sightseeing, swim-and-sail playpen outings, wedding and wedding-party charters, engagement and proposal cruises, Navy Pier fireworks cruises, and group yachting aboard larger vessels.
Trips operate aboard a fleet that includes a 37' sailboat, the S/V Dragonfly, and the larger Yacht Guppy for big groups. Each charter includes a USCG-certified captain responsible for navigation, safety briefings, and a professionally managed experience. Add-on services include premium drink packages with pre-ordered wine, champagne, beer, and seltzer, and guests are welcome to bring BYOB snacks and beverages on most cruises.
Bookings are designed for private groups seeking a tailored event on the water, from romantic two-hour engagements to four-hour celebration charters and three-hour fireworks cruises. On A Boat Sailing highlights clear departure logistics from Chicago waterfront locations and offers complimentary light snacks and select beverages on several trips. Safety and comfort are emphasized through certified captains, fully equipped yachts, and adherence to local maritime regulations. The business is positioned for authentic Lake Michigan experiences, delivering skyline views, swimming stops, and customizable itineraries for family gatherings, corporate outings, and special events. On A Boat Sailing provides transparent trip summaries, duration options, and vessel details so prospective guests can choose the best private charter for their occasion. Seasonal options.
Location
Chicago, IL
Departures on Lake Michigan
Boat Types
37' sailboat, S/V Dragonfly, Yacht Guppy
Multiple luxury vessels available
Private Charters
9 trip types
Designed for private groups
Certified Captain
USCG-certified
Safety and professional operation
Select a trip, confirm a USCG-certified captain, and customize drinks and itinerary for an unforgettable Lake Michigan charter.
Bring sun protection
Apply sunscreen and wear protective clothing to stay comfortable during the cruise.
Arrive early
Arrive 15 minutes before the departure time for smooth boarding and some time to relax.
Stay hydrated
Drink plenty of water, especially on warm days, to stay energized.
Prepare for water activities
Bring a swimsuit if you plan to swim, and consider bringing a towel.
Sunscreen
Protect your skin from sunburn during the cruise.
summer
Hat and sunglasses
Shield your eyes and face from direct sunlight.
summer
Swimsuit
Optional for swimming or water activities.
summer
Water bottle
Stay hydrated throughout the cruise.