CRUISE. RELAX. EXPLORE. LIVE.

Yachts and boat rentals in Chicago

Our Yacht Fleet

Welcome to Windy City Yacht Rentals, your premier choice for boat rentals and luxury yacht experiences in Chicago. We offer a wide range of boats and yachts for all your boating needs, whether you’re planning a corporate event, a private celebration, or simply a day out on the beautiful waters of Lake Michigan.

As the top boat rental service in Chicago, we take pride in providing our clients with unforgettable experiences. Our experienced captains and crew are dedicated to ensuring your safety and comfort while delivering exceptional service throughout your journey. Whether you’re cruising along the magnificent Chicago skyline or exploring the serene waters of Lake Michigan, our team is here to make your boating experience extraordinary.

Discover the true meaning of luxury with our sophisticated yachts, perfect for hosting private parties or corporate events. With spacious decks, elegant interiors, and top-notch amenities, our yachts provide the ideal setting for creating lasting memories. From intimate gatherings with friends and family to grand celebrations, we have the perfect yacht to meet your needs.

At Windy City Yacht Rentals, we understand that every event is unique, and we offer customizable packages to cater to your specific requirements. Our dedicated team will work closely with you to curate a personalized experience, ensuring that every detail exceeds your expectations.

Experience the thrill of cruising the waters of Lake Michigan, taking in the breathtaking views of Chicago’s iconic skyline. Whether you’re seeking a peaceful day of boating or an exhilarating party on the water, our boat rentals and yacht charters offer a variety of options to suit your desires.

Make your reservation today and let Windy City Yacht Rentals provide you with an unforgettable boating experience in the heart of Chicago.

44' SEARAY SUNDANCER​
Type: Motor Yacht
Capacity: 13 People
Make Model: Sea Ray Sundancer
Rental Min: 3 hours
Year: 2002
Cancellation: Full Refund 5 Days Prior
Length: 44 ft
$ 350/hr

Prices incude All captain, gas, and docking fees

44' SEARAY EXPRESS
Type: Motor Yacht
Capacity: 13 People
Make Model: Sea Ray 400 Express
Rental Min: 3 hours
Year: 2003
Cancellation: Full Refund 5 Days Prior
Length: 45 ft
$ 350/hr

Prices incude All captain, gas, and docking fees

44' SEARAY EXPRESS
Type: Motor Yacht
Capacity: 13 People
Make Model: Sea Ray 400 Express
Rental Min: 3 hours
Year: 2003
Cancellation: Full Refund 5 Days Prior
Length: 45 ft
$ 350/hr

Prices incude All captain, gas, and docking fees

Get a Price Quote

LOOKING TO BOOK YOUR NEXT CHARTER?

BOOK YOUR CHARTER ONLINE

1

Use our easy online booking platform (by clicking HERE) to select your yacht, date, and time directly online in less than 60 seconds. 

HIRE YOUR CAPTAIN

2

After booking, you will receive a confirmation email with instructions on how to hire a captain from a list of approved operators.

ENJOY THE WATER!

3

Refer to your confirmation email for directions, items to bring, and safety information. Enjoy the day on the water with your hired crew!

Testimonials on Windy City Yacht Rentals

Paige A.
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I had an amazing experience with Windy City Yacht Rentals! The staff was so friendly and accommodating. The yacht was stunning and the views of Chicago from the water were unforgettable. I highly recommend them for any special occasion or just a fun day out on the water.
Adam G.
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The Party Pontoon was the perfect choice for our bachelorette party! The sound system was great and we had so much space to dance and have fun. The captain was very knowledgeable and made sure we had a safe and enjoyable experience. I would definitely book with Windy City Yacht Rentals again.
Stacy E.
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What a fantastic day on the Sunrise yacht! The boat was beautiful and the crew was top-notch. We enjoyed a relaxing day on the water with incredible views of the Chicago skyline. The booking process was seamless and the pricing was very reasonable. Highly recommended!
Carmenita P.
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I can't say enough good things about Windy City Yacht Rentals. The staff was so professional and went above and beyond to make sure our corporate event was a success. The yacht was impressive and had all the amenities we needed. It was truly a memorable experience for our team.
Michael H.
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The Sundance yacht was the perfect choice for our family reunion. We had a group of 10 and everyone had plenty of space to relax and enjoy the day. The yacht was luxurious and the crew was so friendly and accommodating. We will definitely be booking with Windy City Yacht Rentals again!
Sarah Yi.
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We had a blast on the Speedster! The captain was knowledgeable and gave us a thrilling ride on the water. The yacht was clean and well-maintained. It was the perfect choice for a fun day out with friends. I highly recommend Windy City Yacht Rentals for your next adventure on the water.
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