Experience the magic of Chicago from the water on a private fireworks cruise aboard the S/V Dragonfly. Enjoy spectacular city views, champagne, and unforgettable firework displays over Lake Michigan.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
3 hours
Fitness Level
No special fitness required; suitable for all ages
Wildlife
History
Lake Michigan has served as a vital transportation route since the 19th century, shaping Chicago’s development.
Conservation
Efforts to preserve Lake Michigan’s water quality ensure future generations can enjoy its beauty.
On A Boat Sailing
Experience the magic of Chicago from the water on a private fireworks cruise aboard the S/V Dragonfly. Enjoy spectacular city views, champagne, and unforgettable firework displays over Lake Michigan.
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 the best views
Arriving 15-30 minutes before departure ensures you get prime spots on the boat deck.
Bring a camera or smartphone
Capture stunning photos of the fireworks and city skyline during the show.
Dress comfortably, bring layers
Even summer evenings can be cool on the water; layer up accordingly.
Stay hydrated and snack well
Light snacks and staying hydrated keep you comfortable during the cruise.
Sunscreen
Protects your skin during the daytime portions and when the sun is out.
summer
Camera or smartphone
Capture the fireworks and city views for lasting memories.
summer
Light jacket or sweater
Evenings can be breezy; bring layers to stay warm.
summer
Sunglasses
Reduces glare and enhances your view during the day.
summer