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With Captain
Lively Chicago lake days with skyline views, easy trips to the Playpen or quieter harbors, and a relaxed, fun vibe that guests say makes the whole weekend.
Well-kept Sea Ray Sundancer praised for being very clean, with ample room for groups to spread out, relax, and enjoy the water comfortably.
Consistently high-rated team known for being friendly, patient, and well-organized, with multiple trusted captains delivering smooth, stress-free outings.
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AI Overview
Owner's Description
Spend the day on the beautiful Lake Michigan in Chicago by boat! Charter the 38ft Sea Ray Sundancer Motor Yacht for charterer plus 12 guests plus the captain. Rate as low as $350 per hour and a minimum booking of 3 hours. I have 5 identical Sea Ray Sundancers to choose from. Rates: - Starting at $350 per hour (minimum of 3 hours) - Captain Fee: $125 per hour (Get My Boat will pay Captain direct.) Fuel & Gratuity are extra • Fuel - Playpen $200 River $300 Our Yacht Rental Policies Hours of Operation: 9 AM - 11:00 PM (Seven Days a Week) Weekend trips times are: 10am-2pm, 2:30pm-6:30pm, 7:00pm-11pm Custom Charters Available *Owner can provide a list of USCG Certified Captains from which to choose from for your yacht rental voyages. Weather-related rescheduled charters do not expire and can be used at a later date.
Captain James
440 total bookings
Superowner
Best of 2026
- Capacity
- 12 guests
- Luxury, Events & Large groups
- Motor Yacht
Reviews
(7 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
VB
Victoria
Everytime I've driven on Lakshore Drive and seen all the people out in their boats having fun, I've thought about how nice it would be to rent one. I finally did for my birthday and it was a perfect afternoon! Boat very clean, well-managed, and friendly and helpful captain. Will rent again from Cap't James.
RT
Rya
I’d highly recommend Captain James’ boating charter! My friends and I went to the playpen and had the best time. The boat had plenty of room for our group and was very clean. We used Captain Daniel Chavez for our charter. He was awesome! Overall this was a great experience!!
MP
Michelle
Wonderful time and will definitely book again!
LS
Lavanya
Great experience! Loved the boat!
CE
Cheryl
Had the best time on the boat. The whole team was incredible. They were friendly, patient and the group had a blast. Our boat day really made the entire weekend. Would 10/10 recommend and will be using them again!
Captain James
440 total bookings
Superowner
Best of 2026
I am a USCG Licensed Captain. I take great pride in my knowledge and comfort on the water. You are assured to have a great time, eating, drinking, sunning, and listening to your favorite play lists on my custom stereo system Bluetooth enabled.
Features & Details
- Sea Ray
- 38 Sundancer
- Capacity: 12 people max
Safety Equipment
Life Jackets (1)
Operating Equipment
Generator
Guest Amenities
Air Conditioning, Climate Control
Cabins (1)
Toilets (1)
Leisure & Entertainment Equipment
Bluetooth
Sound System
Departure Location
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
3155 South DuSable Lake Shore Drive
Chicago, Illinois, 60616
United States
Departure Location
41.8354674,-87.6029012
Chicago, Illinois, 60616
United States
Cancellation Policy
50% refund of offer amount up to 15 days prior.
Additional Terms & Information
Our Yacht Rental Policies: Cancellations: - Free cancellations until 30 days before the booking start time. - 50% refund for cancellations between 15-30 days before the booking start time. - Cancellations within 14 days of the booking start time are non-refundable. Hours of Operation: 10 AM - 11 PM TIME SLOTS 10AM-2:00, 2:30PM-6:30PM, 7PM-11PM *Owner can provide a list of USCG Certified Captains from which to choose from for your yacht rental voyages.
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