Chicago's Most Curated Boat and Yacht Rentals
We make the arrangements. You make the memories
Discover Smart Boating- Just Click and Book!
LETS GO BOATING!
40 Feet of Pure Luxury and Performance
This sleek vessel blends sophistication, comfort, and advanced technology, perfect for thrilling adventures or serene relaxation. Enjoy a spacious, elegantly designed cockpit, a generous swim platform, and an outdoor galley with grills, sink, and refrigerator for easy entertaining.
75 Feet of Gorgeous Indulgence
Experience the ultimate Chicago getaway aboard a luxurious 75-foot super yacht! Glide along the iconic skyline, sipping on cocktails as the city’s architectural marvels unfold before you. Bask in the sun on expansive decks, indulge in gourmet bites, and dive into crystal-clear waters.
50 Feet of Sweet Sea Ray!
A gorgeous 50’ yacht that can accommodate 13 people. Whether you're planning a social gathering, bachelorette/bachelor party, proposal, or corporate event, The Sparrow will provide you the best boat rental experience in the Chicagoland area!
Chicago's Largest 49 Passenger Yacht!
Offers the largest cruise vessel in the 49-passenger boat category in Chicago. For a comparable price the Sophisticated Lady offers more cabin space, deck space, total square footage than any other yacht in its class.
26 Feet of Jet Power - Playpen Bound!
Cruise Lake Michigan with 10 friends on a 25 foot Yamaha 252SE Jet Boat! Enjoy the freedom to speed, cruise, or just anchor down and sunbathe at the playpen. Boat is easy and fun drive if your experienced or hire a captain and enjoy the day!
Transport Boats
We will safely and responsibly transport your boat from 30 feet to 70 feet from any marina in Chicago to any winter. storage location via lake or river. 1/2 day or full day rates.
More Amazing Yachts From Anchor Rides! Just Click and Book
The Famous 50 Foot Debonair
Voted Best Charter Experience in Chicago 6 years in a Row! Debonair is a 50' SeaRay Yacht with 2 levels. She is privately owned and has more than enough room for 12 guests. She has a huge sundeck out front, and a great swim platform area to allow you to enjoy the sun.
The Magnificent 43 foot Galeon
Experience Chicago yachting at its finest with this perfect boat. Its skybridge offers an open convertible feel, ideal for enjoying the scenery. Enjoy prime seating upfront for fireworks, while the expanding couch area at the rear accommodates larger groups comfortably.
Extraordinary 54 foot Sea Ray
Hypnotize Luxury Yachts: Exclusively modern vessels exuding Italian sophistication, guaranteed to leave you breathless. Experience luxury yacht rentals in Chicagoland with Hypnotize Luxury Charters, catering to both locals and visitors.
Amazing 46 foot Prestige
Located in downtown Chicago at Burnham Harbor, The GYPSY SOUL offers a luxurious private yacht rental for up to 13 passengers, perfect for any occasion. Experience a luxury lifestyle with cabin space, a 2-story deck, multiple bathrooms, a kitchen, and more!
The Perfect Charter Boat
Elevate your special occasions with a touch of luxury by celebrating on our exquisite yachts. Whether it's a birthday bash, anniversary celebration, or corporate event.
50 Foot Unique Cranchi Yacht
Be unique: this is the only model in Chicago! Italian Beauty! Cruise aboard the luxury 50ft Italian yacht. This stunning example of Italian craftsmanship combines innovative design, jaw-dropping joinery and workmanship add world-class performance.
Discover Smart Boating
We make the arrangements. You make the memories.
We believe that exceptional experiences are crafted by extraordinary individuals. Start your journey by choosing from Chicago's most elite captains – captains who don't just navigate waters but orchestrate unforgettable adventures.