Private Chicago Yacht Charters on Lake Michigan

On A Boat Sailing — Chicago boat charters on Lake Michigan

Private charters, sunset cruises, and fireworks tours

On A Boat Sailing provides private boat charters in Chicago tailored for groups seeking a memorable Lake Michigan experience. Popular options include the Skyline Sunset Cruise, Navy Pier Fireworks Cruise, multi-hour Sail & Swim outings, and specialized event charters for proposals, engagements, and wedding parties. Each charter is operated with a USCG-certified captain, and vessels include a 37' sailboat, the S/V Dragonfly, and the larger Yacht Guppy for bigger groups.

Why choose a private yacht charter in Chicago

• Direct views of the Chicago skyline from the water.
• Flexible private itineraries for celebrations and corporate outings.
• Certified captains and fully equipped yachts for safety and comfort.
• Options to swim at designated lake playpen areas on longer charters.

Featured trips and what they include

Skyline Sunset Cruise — A 2.5-hour private sail along the Chicago lakefront offering skyline views and BYOB-friendly options. Ideal for happy hours and intimate groups.

Navy Pier Fireworks Cruise — A three-hour private cruise aboard the S/V Dragonfly timed for Navy Pier fireworks, with complimentary champagne and seltzer on select departures.

Sail & Swim / Playpen Charters — Multi-hour sail and swim experiences that include anchoring at popular swim playpen areas on Lake Michigan.

Proposals, Engagements, and Wedding Party Charters — Short romantic cruises or extended private charters designed around photo opportunities, toasts with champagne, and customizable itineraries.

Premium Drink Packages — Pre-ordered beverage packages featuring wine, champagne, beer, and seltzer for streamlined service and convenience during the charter.

Booking, logistics, and what to expect

• Departures operate from Chicago lakefront locations; scheduling varies seasonally.
• Private charters are ideal for groups seeking exclusive use of a vessel.
• Clear trip summaries list duration, vessel type, and included amenities to help choose the right experience.

Keywords and search phrases

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Final notes

On A Boat Sailing focuses on private, customizable lake experiences in Chicago with certified captains and multiple vessel options. Prospective guests can select trip duration, beverages (including premium drink packages), and special-event add-ons to create a tailored charter on Lake Michigan.