Discover Chicago’s stunning skyline from the water on a private sunset cruise. Enjoy scenic views, BYOB snacks, and a relaxed atmosphere onboard a luxurious sailboat.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2.5 hours
Fitness Level
Minimal physical activity required, suitable for most guests
Wildlife
History
Chicago’s lakefront has been a vital part of the city’s development since the late 19th century, shaping its maritime culture.
Conservation
Operators strive to minimize environmental impact by adhering to sustainable boating practices and maintaining the water quality.
On A Boat Sailing
Discover Chicago’s stunning skyline from the water on a private sunset cruise. Enjoy scenic views, BYOB snacks, and a relaxed atmosphere onboard a luxurious sailboat.
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.
Arrive early for best seating
Getting to the dock early ensures you secure the best spots and a more relaxed start.
Bring your favorite drinks and snacks
Enhance your cruise experience by bringing beverages and small bites to enjoy while sailing.
Dress in layers
Wind can be cooler on the water, so wear layers to stay comfortable during the trip.
Book in advance for weekends
Weekend cruises tend to fill quickly, so reserve ahead to secure your preferred date.
Sunscreen
Protect your skin during sunny hours on the water.
summer
Hat or visor
Shield your face from sun exposure while sailing.
summer
Light jacket or windbreaker
Stay comfortable if it gets breezy or cooler along the lake.
spring; fall; winter
Camera or smartphone
Capture scenic views and memorable moments from the boat.