High Demand
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With Captain
Easy, organized outings on Lake Michigan with a lively yet relaxed vibe, from playpen parties to smooth sunset cruises that feel seamless and memorable.
Clean, well‑maintained motor yacht with a strong sound system, spacious layout, lily pad and cooler setup, ideal for hanging out, swimming and music on the water.
Consistently praised for clear pre-trip communication, responsive planning and professional captains who keep everything smooth, friendly and stress-free from dock to return.
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AI Overview
Owner's Description
Charter a 39ft Sea Ray 380 Sundancer Motor Yacht on Lake Michigan in Chicago. The vessel accommodates charterer plus 12 guests plus captain. Five identical Sea Ray Sundancer yachts are available. Rates: Starting at $350 per hour with a 3-hour minimum, for up to 12 guests plus captain and crew. Captain fee is $125 per hour. Fuel and gratuity are additional charges. Fuel costs: playpen area $200, river $300. A list of USCG certified captains is available for selection for your yacht charter. Hours of operation: 10 am to 11 pm Weekend trip times: 10am-2pm, 2:30pm-6:30pm, 7:00pm-11pm Guest Amenities: Berths, cabins, sun protection, toilets, Wi-Fi Captain is optional. Weather-related rescheduled charters do not expire and can be used at a later date.
Captain James
437 total bookings
Superowner
Best of 2026
- Capacity
- 12 guests
- Luxury, Events & Large groups
- Motor Yacht
Reviews
(147 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
42 photos have been added by reviewers who booked this listing.
KR
Karuna
Best captain ever!
Kathleen
Had such a great girls day! Timely send off, clear communication, clean boat with a lily pad and cooler for drinks. an overall perfect boat day. Thanks!
HB
Haniyyah
Thank you for an amazing experience! My friends and I had a fantastic time on Lake Michigan. The boat was clean and well-maintained, the sound system was great, and our captain was professional, friendly, and made sure we had an incredible time. Everything on the water exceeded our expectations.
SK
Sophie
The boat owner was very responsive in pre-messaging and what was included and needed to be done prior to departure. Captain Courtney was also the best and great with communication. Overall, the experience was very seamless and very organized I was really pleased and would recommend using Captain James and Courtney for any future boat rentals I'd do.
Marissa
We had a great time in the playpen! Very professional crew and everything went smoothly. Would highly recommend! No better way to spend a hot summer day than out on a boat.
Captain James
437 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
- 380 Sundancer
- Capacity: 12 people max
Safety Equipment
Life Jackets (12)
Operating Equipment
Autopilot
Guest Amenities
Berths (1)
Cabins (1)
Sun Protection
Toilets (1)
Wi-Fi
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
Cancellation Policy
50% refund of offer amount up to 15 days prior.
Additional Terms & Information
Refundable Security Deposit: (Required for Booking / Liability Purposes): • $500 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. *Owner can provide a list of USCG Certified Captains from which to choose from for your yacht rental voyages.
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