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With Captain
Relaxed, upscale cruises along the Chicago shoreline, with skyline views, easygoing hosting, and a welcoming vibe that makes outings feel special and memorable.
Well‑kept, comfortable yacht consistently noted as clean and carefully maintained, giving guests a polished setting to enjoy Chicago’s lakefront scenery.
Highly praised crew for warm, professional hosting and strong focus on safety, helping guests feel both well cared for and free to enjoy their time onboard.
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AI Overview
Owner's Description
Are you looking to experience the best part of Chicago this summer? Join us for a private excursion along the beautiful Chicago shoreline, on the 46 foot luxury yacht, “Great Laker,” located at north Belmont Harbor. MAXIMUM # OF PASSENGERS IS 6. WE DO NOT GO DOWN THE CHICAGO RIVER. Rates as follows: • Weekdays (Monday - Thursday) $350/hour with 3 hour minimum. • Weekends (Friday - Sunday) $400/hour with 3 hour minimum. • Holidays (Memorial Day, July 4, Labor Day) $450/hour with 3 hour minimum. • Special Event Days - Black Yacht Weekend, Scene Party, Air Show (Friday - Sunday) $450/hour with 3 hour minimum. Captained by a USCG fully licensed merchant mariner. Vessel is in full compliance with all USCG and city of Chicago licensing, rules and regulations.
TP
Terry
53 total bookings
- Capacity
- 6 guests
- Luxury, Events & Large groups
- Motor Yacht
Reviews
(38 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
25 photos have been added by reviewers who booked this listing.
Danielle
We had the absolute BEST experience with Captain Terry and Vanessa on our Lake Michigan boat charter in Chicago! From the moment we stepped aboard, we were warmly welcomed and felt completely at ease. Terry and Vanessa are not only experienced and professional, but also genuinely kind and fun people — they truly made our time on the water unforgettable. Their boat was beautiful, clean, and incredibly well-maintained. You can tell they take pride in every detail. We especially appreciated how safety-conscious they were, which made it easy for us to relax and enjoy the ride. They gave us the perfect balance of hosting and letting us do our own thing — we never felt rushed or restricted, just completely cared for and free to enjoy the experience. We had such a wonderful time cruising along the Chicago skyline and taking in the amazing views. Whether you’re celebrating something special or just looking to enjoy a peaceful and memorable day on the lake, Terry and Vanessa are the crew you want. We would absolutely book with them again and highly recommend them to anyone looking for an exceptional boat day!
Rafael
Vanessa and Terry were the best. The boat is great and we had such a great time. We highly recommend to book a trip with them. Thank you for having us and we will come back for sure.
GG
Gina
Terry and Vanessa were great and more than accommodating. My girlfriends and I celebrated my bday and the day was perfect. You won’t be disappointed when booking them it’s the perfect #summertimeCHI experience!
KR
Kim
Terrry and first mate Vanessa were amazing We are a family of 6 had an amazing time on the lake. They were safe and fun and met everyone’s needs above and beyond. Highly recommend this team we will be back Thank you❤️ Kim and Alan and family
AB
Ashley
Terry and his wife made are trip amazing. They were super polite and helpful the whole trip. They took us out on the lake and gave us a nice small tour. We arrived 30 mins late and they were kind enough to still give us our full time. I will be booking with them again.
TP
Terry
53 total bookings
I am a USCG licensed merchant mariner and have been boating for over 40 years. Safety is my main concern. Providing a memorable fun experience for my passengers is second!
Features & Details
- Maxum
- Custom
- Capacity: 6 people max
Safety Equipment
Life Jackets (1)
Guest Amenities
Oven
Sun Protection
Departure Location
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
2 West Belmont Harbor Drive
Chicago, Illinois, 60657
United States
Departure Location
Cancellation Policy
Free cancellation up to 7 days before your trip.
Additional Terms & Information
Because the weather in Chicago can be unpredictable we reserve the right to cancel the charter at any time. We will do our best to monitor the waves and weather. You will be fully refunded if we need to cancel.
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