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With Captain
Relaxed, social outings on the water with skyline views and plenty of room to hang out, celebrate, and enjoy a laid‑back Chicago cruise.
Spacious layout with ample seating for groups; shows some cosmetic wear but guests report comfortable, enjoyable outings overall.
Experiences vary: some note prompt captains and smooth trips, while others mention slower communication and occasional late departures.
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AI Overview
Owner's Description
Create Lasting Memories on the Water Step aboard our luxurious 51-foot Sea Ray Sundancer and experience Chicago from a whole new perspective. Whether you're spending the day anchored in the famous Playpen, cruising along the city's iconic skyline, watching the Navy Pier fireworks, or exploring the Chicago River, your private yacht charter is designed for relaxation and unforgettable moments. Perfect for birthdays, bachelor and bachelorette parties, corporate outings, family celebrations, or simply a day with friends, the yacht comfortably hosts up to 12 guests, plus a licensed captain and crew. With spacious seating, premium amenities, and incredible views of Lake Michigan, every charter is tailored to create an exceptional experience. Choose Your Ideal Charter Chicago Skyline Cruise Take in panoramic views of Chicago's renowned architecture and waterfront while cruising Lake Michigan. Playpen Experience Drop anchor at Chicago's most popular boating destination to swim, relax, sunbathe, and enjoy the atmosphere. Chicago River Cruise See the city from the historic Chicago River and admire its famous bridges and buildings. (Available with a minimum 4-hour charter. Not offered on Saturdays.) Navy Pier Fireworks Cruise Enjoy a front-row seat to Chicago's spectacular fireworks display over the lake on Wednesday evenings (9:00 PM) and Saturday nights (10:00 PM). Charter Policies - Maximum Capacity: Up to 12 guests, plus captain and crew. Capacity limits cannot be exceeded. - No Boat Tie-Ups: For safety and insurance purposes, rafting or tying up with other vessels is not permitted. - Alcohol: Guests must be 21 years of age or older to consume alcoholic beverages. - Bareboat Charter Agreement: All charter guests must complete the required agreement before departure. - Swimming: Swimming is permitted at your own risk. There is no lifeguard on board, and all guests must sign a waiver prior to entering the water. - Food & Beverages: Please avoid bringing red wine, dark-colored juices, or other items that may stain the yacht. - No Hidden Fees: Fuel and standard cleaning are included in your charter price. HOLIDAYS & SPECIAL EVENTS - Black Yacht Weekend (June 20) - 4th of July Weekend (July 4) - Black Scene Party (July 19) - Chicago Boat Scene Party (July 25) - Air and Water Show (August 15-16)
Paul
49 total bookings
- Capacity
- 12 guests
- Luxury, Events & Large groups
- Motor Yacht
Reviews
(6 reviews)
Listing Accuracy
GoodDeparture & Return
GoodVessel & Equipment
OkayCommunication
GoodValue
GoodItinerary & Experience
Good
2 photos have been added by reviewers who booked this listing.
Richie
We had a great time on Paul’s boat for my birthday. The boat had everything we needed and was a really good value. Would book again!
MO
Myka
I had a great experience with lake shore boat charters. Paul was very responsive and my friends and i had a great time on the water celebrating my birthday
Kyleigh
We had a great time, plenty of space for 9 girls!
JC
James
Boat is showing wear but nothing negative to say about the experience. Captain was prompt on departure/arrival times. Found email to be the best way of contacting.
Fabiana
I am leaving a fairly "ok" rating. Our boat was scheduled for 3pm. I got a text from the captain that he would be 15 minutes late but add that onto our reservation. He was moreso 30 minutes late. This wasn't a big issue, but the vessel was left in a poor condition by the group prior. They left wet towels, trash, etc. Paul was also not the most communicative. Sometimes, I would wait days for a response. Had a fun time nonetheless, but would book elsewhere if I could.
Paul
49 total bookings
Our fleet is situated at 31st Harbor. We’ve been chartering boats for 4 years and enjoy offering boating experiences to for a wide variety of occasions. We look forward to hearing from you!
Features & Details
- Sea Ray
- Sundancer 44
- Capacity: 12 people max
Safety Equipment
Life Jackets (12)
Operating Equipment
Depth Sounder
Generator
Guest Amenities
Air Conditioning, Climate Control
Cabins (1)
Oven
Sink
Sun Protection
Toilets (1)
Leisure & Entertainment Equipment
Bluetooth
Sound System
Indoor dinning Area
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
Cancellation Policy
Free cancellation up to 14 days before your trip.
Additional Terms & Information
Weather Policy Our company has the responsibility to decide if weather conditions are suitable for chartering and they may classify conditions as either “charterable” or “uncharitable”. Uncharitable conditions usually include severe weather conditions like heavy storms, small craft advisory warnings, gale storms, strong winds, and large waves. On the other hand, light rain, passing storms, and cooler temperatures are generally considered acceptable for chartering. If the conditions are deemed uncharitable, the team will collaborate with the charterer to reschedule or temporarily postpone the charter to a later date. If a reschedule is necessary, we will give a rescheduling credit to the charterer that can be used for a charter of the same or lesser value within one year. Cancellation Policy The policy for cancelling a charter involves a non-refundable fee of 5%. If a cancellation request is made at least 14 days before the charter date, a full refund will be given, but the non-refundable fee still applies. If the cancellation request is made within 5 days of the charter date, a 50% refund will be given, less the non-refundable fee. If the cancellation request is made within 3 days of the charter date, there will be no refund. Cancellation requests must be made in writing via email and should include: - The Charterer’s name - Organization name (if applicable) - Scheduled date and time of charter - Reason for cancellation - A request for cancellation. Rescheduling a charter does not allow for a full refund as per this policy. For more information, please refer to the company’s Terms & Conditions regarding their weather and cancellation policy.
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