Set sail on Lake Michigan aboard the luxurious 51′ Sea Ray Sundancer Powerboat. This boat offers comfort, stunning views, and the chance to swim or relax in style. Discover what makes this Chicago adventure truly special.
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Difficulty
easy
Duration
4–8 hours
Fitness Level
Suitable for most fitness levels; minimal physical activity required
Wildlife
History
Lake Michigan has been a vital part of Chicago's development since the 19th century, shaping commerce and recreation alike.
Conservation
The boating company promotes eco-friendly practices to preserve the lake’s natural beauty.
Chicago Sailboat and Yacht Charters
Set sail on Lake Michigan aboard the luxurious 51′ Sea Ray Sundancer Powerboat. This boat offers comfort, stunning views, and the chance to swim or relax in style. Discover what makes this Chicago adventure truly special.
Chicago Sailboat and Yacht Charters offers private boat charters on Lake Michigan departing from Chicago, Illinois. The company specializes in three main experiences: the 51′ Sea Ray Sundancer powerboat, the 35′ Sea Ray Sundancer powerboat, and a Sunset Cruise that highlights Chicago’s skyline. Each offering includes on-board amenities described in the trip summaries and opportunities for swimming, relaxing on sun pads, and viewing city landmarks.
On the 51′ Sea Ray Sundancer powerboat guests find spacious lounging areas, two bedrooms, two bathrooms, a sun pad, and a four-person inflatable raft for swimming. The 35′ Sea Ray Sundancer powerboat features A/C, a bedroom, and a large bathroom, and is available for three- to eight-hour trips. The Sunset Cruise follows a scenic route past Willis Tower, Buckingham Fountain, Navy Pier, and other downtown sights, with options for evening skyline views and nightly fireworks at Navy Pier when scheduled.
The operator focuses on safe, private charters and encourages groups to bring personal snacks and drinks for a comfortable day on the water. Trips depart from Chicago and run on Lake Michigan waters; all descriptions reflect the actual boat models and trip experiences listed. Dates, times, and availability vary by booking; customers should consult the operator for exact schedules, guest capacity, pricing, and safety information prior to reservation.
Chicago Sailboat and Yacht Charters presents straightforward, amenity-focused lake charters for visitors and locals seeking private boating, skyline views, swimming, and special-event cruises. Experienced crew manage each trip following safety checks and clear communication procedures for guests.
Boat Models
51' & 35' Sea Ray
Spacious, amenity-rich vessels
Routes
Lake Michigan
Scenic Chicago skyline routes
Trip Length
3–8 hours
Flexible durations available
Tours Offered
3 tours
Private charters for groups
Select a 51′ or 35′ Sea Ray Sundancer or book a Sunset Cruise — check availability and plan snacks and drinks for your trip.
Bring Sun Protection
Apply sunscreen and wear hats to stay comfortable during the daytime hours.
Pack Snacks and Drinks
Bring your favorite snacks and beverages for a customized on-water picnic.
Have Waterproof Gear
Carry waterproof gear if you plan to swim or get close to the water.
Check Weather Conditions
Review the forecast before your trip to ensure safe and enjoyable sailing.
Sunscreen
Protects your skin during long hours in the sun.
summer
Swimsuit
Ideal for swimming or lounging in the water.
summer
Hat and Sunglasses
Shield your eyes and face from sun glare.
summer
Light Clothing
Keeps you cool and comfortable on deck.
summer