Glide along Lake Michigan with Chicago Sailboat and Yacht Charters on a four-hour sunset cruise offering dramatic skyline views, a refreshing swim, and summer fireworks at Navy Pier. Perfect for romantic evenings or special celebrations.
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Difficulty
easy
Duration
4 hours
Fitness Level
No special fitness required; accessible to most ages and fitness levels
Wildlife
History
Lake Michigan has been a transit route and recreational hub since the city's founding in the early 19th century, with its shoreline evolving into a vital urban waterfront.
Conservation
Chicago Sailboat and Yacht Charters follows sustainable boating practices to minimize impact on Lake Michigan's ecosystem, encouraging guests to respect the fragile lakeshore environment.
Chicago Sailboat and Yacht Charters
Glide along Lake Michigan with Chicago Sailboat and Yacht Charters on a four-hour sunset cruise offering dramatic skyline views, a refreshing swim, and summer fireworks at Navy Pier. Perfect for romantic evenings or special celebrations.
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 a Light Jacket
Lake Michigan breezes intensify as the sun sets; a light jacket keeps you comfortable.
Arrive Early for Boarding
Arrive at least 15 minutes before departure to get settled and receive safety instructions.
Prepare for Limited Mobility
Boat decks can be tight; wear sturdy shoes and be mindful while moving around.
Stay Hydrated and Use Sunscreen
Even near sunset, UV rays reflect off the water; protect your skin and drink water regularly.
Light Jacket
Protects against cool, lake-breeze evenings.
spring
Sunscreen
Essential for UV protection on open water.
summer
Comfortable, Non-Slip Shoes
Necessary for safe movement on deck.
Water Bottle
Stay hydrated during the cruise.