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With Captain
Guests describe unforgettable Chicago outings with smooth rides, lively yet comfortable vibes, and easy, low-stress planning from harbor to return.
Well-kept Sea Ray offers a relaxed floating oasis feel, praised for smooth cruising and a comfortable setup that works well for celebratory groups.
Renters consistently highlight clear, patient communication, smooth logistics, and friendly, professional captains who keep everyone comfortable and at ease.
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AI Overview
Owner's Description
Discover luxury aboard our prestigious 36-foot Sea Ray yacht docked at Diversey Harbor. This vessel, ideal for up to 13 people, comes equipped with a full bathroom, a dynamic sound system, a comfortable bedroom, and various entertainment spaces. Choose your preferred time for a magnificent powerboat experience: Rental Rates: Weekdays - Monday-Thursday: $190/hour (3 hour minimum) Friday - Sunday Pricing: - April 15th - May 15th Weekends: $190/hour - May 16th - May 31st Weekends (including Memorial Day weekend): $220/hour - June Weekends: Friday $300/hour, Saturday $330/hour, Sunday $300/hour - July/August Weekends: Friday $320/hour, Saturday $350/hour, Sunday $320/hour - September Friday $300/hour, Saturday $330/hour, Sunday $300/hour - October Weekends: $190 an hour *Fuel, Cleaning, and Tax are included in the cost of the rental* Water toys: We have a lily pad available for rent for $60 What's Included: - All required safety gear and life jackets - Bathroom - Bluetooth speaker system - Cooler - Kitchen What To Bring: - Food and beverages (Alcohol is allowed) - Bags of ice - Swimsuit & towel - Phone charger Holidays and special events are subject to a price increase: - Memorial Day Weekend (May 23rd - 25th) - BYW (June 19th- 21st) - 4th of July Weekend (July 3rd - 5th) - Blvck Scene Party (July 11th - 12th) - Chicago Boat Scene Party (July 25th) - Air and Water Show (August 14th - 16th) Captain: The captain rate included in the offer pricing is intended as an indication of the typical captain pricing expected. The actual captain fee will be negotiated between the Charterer and the charterers hired captain. If necessary, an adjustment to the captain rate can be done through GetMyBoat as GetMyBoat will pay the Captain fee portion of the booking rate directly to the captain after the booking is completed. The owner will not be paid the Captain fee. We provide a pre-approved Captain contact list but you have your choice of who to hire. You may hire a different qualified captain through our owner-approval process.
Optional Add-ons
These options can be added during checkout.
Floating Lilly Pad
$60 per trip
KD
Kevin
535 total bookings
Superowner
Best of 2026
- Capacity
- 12 guests
- Powerboats, Pontoons, & RIBs
- Cuddy Cabin/Walk Around
Reviews
(95 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
17 photos have been added by reviewers who booked this listing.
Miguel
Great time and professional captain Riley was a good man all around
BH
BRIAN
We had a great time on this boat and the process was very smooth. Captain AJ was great as well. Would recommend.
AG
Alyssa
Amazing experience!
SG
Samantha
This was the most fun I’ve had in Chicago so far, the weather was beautiful and we had a smooth ride. We rented the boat for a bachelorette and communicating with Kevin was so easy, he was able to answer all of our questions patiently, he was so kind and made the whole process so easy. Our captain was Riley, I would totally recommend him, he was puntual, funny and made our trip so fun and also made us feel so comfortable and safe. He was clear with instructions and was patient with us as well. I would totally recommend Kevin and his boat to everyone!
CR
Ceci
Our charter with Kevin was great and everything was as pictured. There were 8 passengers (aside from the captain), and we were all seated comfortably. Directions to get to the dock as well as directions leading up to the day were very clear & Kevin was very responsive. Definitely recommend booking with him.
KD
Kevin
535 total bookings
Superowner
Best of 2026
Get ready for an unforgettable day on the water in Chicago! With a fleet of four luxury yachts, I offer the perfect boating experience for any occasion—whether you're celebrating, relaxing, or just looking to enjoy the city skyline from the lake. Each yacht is fully equipped with Bluetooth sound systems, coolers, bathrooms, and spacious entertainment areas to ensure a comfortable and fun time. Groups of up to 13 guests can cruise, anchor in the Playpen, or soak up the sun on deck. 📍 Location: Diversey Harbor, Chicago
Features & Details
- Sea Ray
- 330 Sundancer
- Capacity: 12 people max
Safety Equipment
Anchor & Rode
Bilge Pumps
Carbon Monoxide Detectors
Fire Extinguishers
First Aid Kit
Flares
Life Jackets (15)
Lifebuoys
Medical Supplies
Navigation Lights
Navigation Equipment
Oil Pollution Prevention
PFDs (15)
Sound Signals
Tool Kit
VHF Radio
Operating Equipment
Autopilot
GPS ChartPlotter
Inverter
Depth Sounder
Generator
Guest Amenities
Air Conditioning, Climate Control
Berths (1)
Cabins (1)
Fridge
Shower
Sink
Sun Protection
Toilets (1)
Washrooms Onboard
Wi-Fi
Leisure & Entertainment Equipment
Bar
Bluetooth
Sound System
Indoor Lounge Area
Outdoor Lounge Area
Accessories
Water Mat
Departure Location
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
2601 North Cannon Drive
Chicago, Illinois, 60614
United States
Departure Location
41.9294473,-87.634601
Chicago, Illinois, 60614
United States
Cancellation Policy
Free cancellation up to 14 days before your trip.
Additional Terms & Information
Weather Policy: The safety of our guests is our top priority. Therefore, the vessel owner or hired operator has the authority to determine whether weather conditions are suitable for chartering ("charterable") or not ("uncharterable"). Uncharterable weather conditions typically include, but are not limited to, heavy storms, small craft advisory warnings, gale storms, strong winds, and large waves. These conditions pose potential risks to guest safety and may result in rescheduling the charter. If your charter is canceled due to weather, we will issue a credit for the full amount of your booking, which can be applied toward a future charter. This credit does not expire. On the other hand, light rain, passing storms, and cooler temperatures are generally considered charterable. These conditions may not significantly impact the safety and enjoyment of the charter experience. However, please note that the hired operator will still monitor and assess the weather conditions to ensure they remain within acceptable limits for a safe and enjoyable charter.
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