Luxury Sea Ray Sundancer charters and evening sunset cruises departing from Chicago, Illinois on Lake Michigan.
Choose from the 51′ Sea Ray Sundancer, 35′ Sea Ray Sundancer, or the Sunset Cruise.
water-activities · Chicago
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.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Spacious, amenity-rich vessels
Scenic Chicago skyline routes
Flexible durations available
Private charters for groups
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Chicago Sailboat and Yacht Charters listing.
Chicago Sailboat and Yacht Charters offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Select a 51′ or 35′ Sea Ray Sundancer or book a Sunset Cruise — check availability and plan snacks and drinks for your trip.
boat-charters · Chicago
Step aboard Chicago’s Sea Ray 35’ Sundancer for a luxurious day on Lake Michigan. With spacious comfort and smooth rides, this charter boat redefines waterfront adventure.
boat-charters · Chicago
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.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.