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With Captain
Relaxed, social outings on Lake Michigan with smooth rides, city views, music, and plenty of space for birthdays, family gatherings, and summer celebrations.
Spacious, spotless deck with ample seating, strong sound system, and comfortable layout that guests say works well for photos, lounging, and hanging out at the playpen.
Guests praise the captain’s clear communication, flexibility, and local knowledge, noting he’s welcoming, safety‑minded, and often goes beyond expectations to host a great day.
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AI Overview
Owner's Description
Discover the Windy City like never before aboard this 44ft Regal Commodore. This sleek and spacious yacht offers the perfect blend of comfort and style—ideal for cruising Lake Michigan, hosting events, or enjoying a relaxing day on the water with family and friends. At least one guest must be 21 or older on board. Minimum booking: 3 hours Pricing: Monday – Thursday (Yacht + Captain Fee) - $275/hour + $125/hour - 3 hours: $1,125 - 4 hours: $1,500 Friday – SUNDAY (Yacht + Captain Fee) - $325/hour + $125/hour - 3 hours: $1,350 - 4 hours: $1,800 Special Rates Yacht Party Event Weekends (5 hour min) – Message for pricing Holidays: $400/hour + $125/hour Captain (4 hour min) Air & Water Show: $400/hour + $125/hour Captain (4 hour min) Gratuity is not included. Tipping your captain & crew is recommended based on your experience. Experience Details: The spacious cockpit offers comfortable seating, a wet bar, and multiple cup holders to keep your drinks within reach. Enjoy your favorite music with a Bluetooth-enabled sound system, and take advantage of the large swim mat included with your booking. What’s Included: - USCG Licensed Captain - Adult & Kids Life Jackets - Bluetooth Sound System - Cooler with Ice - Large Swim Mat What to Bring: - Towels - Sunscreen - Food & Drinks (Alcohol allowed) Perfect For: - Birthdays - Bridal/Bachelor Parties - Engagements - Family Gatherings - Graduations - Fireworks Nights (Wednesdays & Saturdays) - Cruise & Anchor (Playpen or Monroe Harbor) Additional Services: Wave Star Inc also offers optional photography, videography, and drone services to capture your experience. Cleanliness & Safety Before every charter, the yacht is professionally cleaned and disinfected, including all high-touch surfaces such as railings, seating, counters, and restrooms. Safety and cleanliness are always a top priority. Location: Located at 31st Street Harbor in Chicago, this 44’ yacht is perfect for private events, celebrations, and unforgettable days on the water.
Robert
35 total bookings
- Capacity
- 13 guests
- Luxury, Events & Large groups
- Motor Yacht
Reviews
(9 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
21 photos have been added by reviewers who booked this listing.
SD
Shreerupa
Robert was fantastic. He was very prompt with his communication. The boat was very clean and had plenty of seats and space to accommodate our group of 13. Our primary goal was watching the Air & Water show which was running late. Robert was kind enough to give us extra time for free so that we had the best experience and did not miss the main attraction of the show.
FM
Fernando
Captain Robert gave us an unforgettable day on the water! From the moment we boarded, he made everyone feel welcome and comfortable. His professionalism, local knowledge, and easygoing personality created the perfect balance of safety and fun. The boat was spotless, the ride was smooth, and every detail was taken care of so we could just relax and enjoy. We can’t wait to book with him again — highly recommend!
TH
Thomas
Great trip, all had fun, perfect spot in the play pen.
DS
Deep
We loved the seating area in the boat, setting up our music, getting out on the water, and taking pictures. A 10/10 boat day
MA
Megan
Robert was incredibly flexible with changing weather conditions and extremely responsive to our questions. The boat was a extremely comfortable and in great condition. Robert was a great host and we felt very safe. Highly recommend and would book with him again. Thanks Robert!!!
Robert
35 total bookings
I am excited to be a part of the GetMyBoat movement in making boats more accessible and affordable to others. As well as looking forward to giving our guest a great experience during their booking.
Features & Details
- Regal
- 4160 Commodore
- Capacity: 13 people max
Safety Equipment
Life Jackets (13)
Guest Amenities
Air Conditioning, Climate Control
Cabins (2)
Sun Protection
Toilets (1)
Leisure & Entertainment Equipment
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
Free cancellation up to 14 days before your trip.
Additional Terms & Information
Weather: If you are unable to use the boat due to dangerous weather conditions or heavy sustained rain, (actually happening at time of rental, not based on forecast conditions) you can elect to either reschedule at no charge or to receive a 75% refund of the boat rental rate. Location: We are docked at 31st street harbor which is about a 10 minute Uber ride from downtown. Rental Agreement: A boat rental agreement will be sent by email following the booking confirmation for your review and signature. This agreement must be signed for the rental to proceed. Waivers: Our insurance company requires that all passengers sign a liability waiver. This waiver must be signed by all passengers prior to the boat's departure from the dock.
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