Departure date

Trip duration


Day trip
Multiple days
(Less than 1 week)
Weekly trip
Show boats that have weekly prices. Most weekly boats outside of the US are available only Saturday to Saturday.

Boat type

Boat length: 5ft -

Manufacturer

Boat model

Price

$
$

Captain

Boat build year: -

Amenities

Sort by:
Location
Reset
Dates
Filters
Reset

Departure date


Trip duration

Day trip
Multiple days
(Less than 1 week)
Weekly trip
Boat
Boat Details
Reset

Boat type

Boat length: 5ft -

Price: $ - $

Captain

Manufacturer

Boat model

Filters
Filters
Reset

Boat build year: -

Amenities

16 Captained boat Charters Chicago — Rent a private yacht in Chicago with Sailo!

1 - 16 of 16 boats
  1. Home

Rent a captained boat in Chicago with Sailo

Embark on a unique aquatic adventure in the heart of the Windy City with Chicago captained boat rentals. Sailo is here to provide you with an unforgettable boating experience, offering a range of captained boat rentals in Chicago that cater to both enthusiastic sailors and those new to the joys of boating. Our approach is friendly and direct, ensuring your journey along Lake Michigan and the Chicago River is not just about renting a boat, but about enjoying a memorable day on the water.

Chicago's stunning skyline and historical waterways make it a prime destination for yacht charters. With our Chicago yacht rentals, you have the opportunity to see famous landmarks like Navy Pier, the Magnificent Mile, and the Chicago skyline from a unique perspective. Whether you're looking to rent a yacht in Chicago for a leisurely cruise, a special celebration, or an exciting day out, our fleet will provide you with the perfect vessel for your needs.

When you hire a captained boat in Chicago, you're choosing a stress-free way to enjoy the city's waterways. Our experienced captains are knowledgeable about the best routes and spots, ensuring your trip is safe, enjoyable, and tailored to your preferences. Whether you’re seeking a peaceful afternoon sail or an adventure-filled day, our captains are ready to guide you through an amazing boating experience.

Our premium selection of private captained boat rentals in Chicago

At Sailo, we offer a premium selection of private captained boat rentals in Chicago. Our fleet includes a variety of boats, from luxurious yachts to cozy sailboats, all equipped with the amenities needed for a comfortable and enjoyable voyage. Whether planning an intimate outing or a large gathering, we have the perfect boat to match your occasion.

For those seeking a more personalized and exclusive experience, our captained boat charters in Chicago are the ideal solution. These charters provide the luxury of a private vessel with the added convenience of a professional crew, allowing you to relax and enjoy your time on the water. Chicago captained boat charters are perfect for special events, offering a unique and elegant way to celebrate on Lake Michigan or the Chicago River.

How to find a captained boat rental in Chicago

Finding the perfect captained boat rental in Chicago is easy and convenient with Sailo. Our user-friendly platform allows you to browse through our diverse fleet and select the boat that best fits your needs. You can filter your search by boat type, size, and additional features, making it simple to find your ideal match for a fantastic day at sea.

When searching for private yacht charters in Chicago, consider the type of experience you’re looking for. Are you interested in a leisurely sail along the lakefront, an exploration of the Chicago River, or a day filled with water sports and activities? With Sailo, you can choose a boat and captain that align with your specific interests and preferences, ensuring a personalized and memorable experience.

How much does it cost to charter a captained boat in Chicago for a full day?

The cost of chartering a captained boat in Chicago for a full day varies based on several factors, including the type of boat, its size, and the duration of the rental. Prices can range from a few hundred dollars for smaller vessels to several thousand dollars for larger, more luxurious yachts. It’s important to consider additional expenses like fuel, docking fees, and optional services like catering or special equipment.

When budgeting for Chicago captained boat charters, remember to consider the entire experience. This includes any extra amenities or activities you wish to include, ensuring that your day at sea is as enjoyable and seamless as possible. Our team at Sailo is committed to providing transparent pricing and will help you understand all the costs involved in your boat rental.

Can I rent a captained boat charter in Chicago with a captain?

Yes, you can! Renting a captained boat charter in Chicago with a captain is the best way to enjoy a stress-free and delightful day on the water. Our captains are experienced navigators and knowledgeable guides who can enhance your boating experience. They know the best spots for sightseeing, exploring the city's architectural marvels, or simply relaxing. With a captain on board, you can fully immerse yourself in the experience without any concerns about operating the boat.

Discover the beauty of Chicago with:

Rent a boat near Chicago

Looking to rent a boat near Chicago? We got you covered! Explore Chicago and its amazing surroundings in an instant, with these amazing boats: