Private Chicago Boat Charters — Skyline Views, Swimming & Sunset Cruises

Chicago Sailboat and Yacht Charters — Private Lake Michigan Charters

Discover private boat charters in Chicago, Illinois, with options for day trips, swimming, and sunset skyline cruises. Chicago Sailboat and Yacht Charters operates Sea Ray Sundancer powerboats and curated Sunset Cruises that traverse Lake Michigan and pass landmark sights such as Willis Tower, Buckingham Fountain, and Navy Pier.

Popular Charter Options

• 51′ Sea Ray Sundancer Powerboat: Spacious layout, two bedrooms, two bathrooms, sun pad, and a four-person inflatable raft for swimming. Ideal for groups seeking comfort and multiple on-board amenities.
• 35′ Sea Ray Sundancer Powerboat: A/C, bedroom, and a large bathroom. Available for three- to eight-hour trips, offering a balanced combination of comfort and maneuverability.
• Sunset Cruise: Scenic evening routes showcasing the Chicago skyline, waterfront landmarks, and Navy Pier fireworks when scheduled.

What to Expect on a Charter

Charters depart from Chicago and operate on Lake Michigan waters. Trips emphasize private group experiences, skyline viewing, swimming opportunities (including a floating playpen or swim raft on designated trips), and relaxed onboard lounging. Guests are encouraged to bring personal snacks and drinks for their comfort.

Amenities and Comfort

• Comfortable lounging areas and sun pads for relaxing.
• Sleeping accommodations and bathrooms on Sea Ray Sundancer models.
• Climate control (A/C) on select boats for warm-weather comfort.

Skyline Views and Landmark Routes

Routes commonly pass by downtown Chicago landmarks: Willis Tower, Buckingham Fountain, Navy Pier, and other shoreline highlights. Sunset Cruises offer evening light and skyline photo opportunities; when Navy Pier fireworks are scheduled, cruisers can view displays from the water.

Booking and Trip Length

The 35′ Sea Ray Sundancer lists availability for three- to eight-hour cruises; durations for other charters vary and should be confirmed at booking. Reservations, exact schedules, pricing, guest capacity, and safety requirements are provided directly by the operator.

Safety and Preparation

Charters are private and staff follow pre-departure safety checks and standard boating practices. Guests should confirm safety and capacity details when booking and may bring snacks and beverages for a custom onboard experience.

Who Benefits from These Charters?

• Visitors seeking unique Chicago skyline perspectives from Lake Michigan.
• Local groups celebrating special occasions or hosting private gatherings.
• Photographers and couples looking for sunset or evening cityscape views.

Keywords for Search

Chicago boat charters, Lake Michigan cruises, Sea Ray Sundancer charter, Chicago sunset cruise, private yacht charter Chicago, Navy Pier fireworks cruise, Willis Tower skyline boat tour — these search terms align with the experiences offered.

For accurate availability, pricing, and to confirm vessel amenities, check the operator’s booking information before reserving a private charter in Chicago.