Yacht Rentals

Find and rent the perfect boat in Chicago. Captain optional.

Top Yacht Rentals Chicago

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Chicago, IL


We live it, you’ll love it! Silverton Yacht!

1-6 passengers Captain Included

Chicago, IL


50' Luxury Yacht. Playpen, River cruises up to 12

1-12 passengers Captain Included

Chicago, IL


51' Sea Ray Sundancer powerboat in Burnham harbor

1-7 passengers Captain Included

Chicago, IL


Fun and pleasure on a spacious and luxurious yatch

1-7 passengers No Captain

Chicago, IL


Brand New 3 Bedroom / 2 Bathroom 43' Yacht

1-7 passengers Captain Included

Chicago, IL


Big Boat with plenty of social distancing space!

1-9 passengers Captain Available

How to Rent a Yacht in Chicago

If you would like to rent a yacht in Chicago, you have so many boating options. Chicago is a big city on the shores of Lake Michigan. Chicago may not actually be on the ocean, but the lake is so big that it can easily be mistaken for a sea. Fortunately, the water is usually calm and easy for yachters to navigate in the summer and fall months. Chicago's lakes and rivers can be ideal for weekend trips. Lake Michigan offers world-class sailing as well as places for boat parties, plus the chance for everyone in your crew to enjoy some challenging watersports activities. With Boatsetter, now’s your chance!

Experience Chicago Yachting

When you choose a Chicago yacht rental, you'll get to experience all the beauty of the Chicago River and Lake Michigan and enjoy all kinds of water activities from your boat. Here are some special yachting experiences for you to enjoy.

Chicago Harbor Lighthouse

You can find the Chicago Harbor Lighthouse at the start of the Chicago River. This is one of the three main lighthouses in Chicago, and it was designated an official Chicago Landmark on April 9, 2003. Take a guided tour of the lighthouse or sail out into the harbor to see the lighthouse from the perspective of the millions of other sailors who have been guided by one of Chicago’s most welcoming lights.

Montrose Harbor and Montrose Beach

This is one of the busiest boating areas. There is a modern marina, picnic facilities right near the docks, a wide sandy beach, and party music playing all the time. As with most vantage points in Chicago, this is an excellent place for pictures of the downtown skyline. The beach connects you to the Chicago Riverwalk, a perfect place for a relaxing evening stroll along the water. On a Chicago yacht rental, you can get a close-up view of the impressive skyscrapers and also experience everything else the city has to offer from the water.

Navy Pier

Midwest region. The boardwalks feature concerts, a Ferris wheel, and even fireworks shows on Wednesdays and Saturdays from Memorial Day to Labor Day. If you rent a yacht in Chicago, it is easy to explore the pier from the water and beyond. In addition to the most Chicago Yacht Club Race, Navy Pier also functions as the starting point for many other world-famous sailing competitions.

Chicago's Best Bodies of Water for Yachting

The best bodies of water to explore on your Chicago yacht rental will depend on the type of outing you will be taking. In general, all three of these bodies of water are good ones to visit on a yacht with your family.

Chicago River

For a unique perspective of downtown, sail your Chicago yacht rental along the Chicago River. The architecture will include sights of modern skyscrapers like the Hancock Center, Marina City, Willis Tower, and Trump Tower, as well as historic skyscrapers like the Tribune Tower, The Rookery, and Sullivan Center. The river is where the 333-mile Chicago Yacht Club Race takes place. This is. In the most recent race, 265 of the 266 boats that began in Chicago went the full distance, which is the highest completion rate ever.

Lake Geneva and the Fox River

Sail your Chicago yacht rental out to Lake Geneva and the Fox River. These are some other outdoor areas that are close enough to the city that are great for boating and they are really good options for day trips.

Indiana Dunes National Lakeshore

Another good place to visit is the Indiana Dunes National Lakeshore on the southwest Michigan coast. In the Sleeping Bear Dunes National Lakeshore, you can hike through the forest and along the beach while learning about the ecology of the Great Lakes. A short day trip like this is easy to do, and you can still make it back to Chicago by sunset.

Best Yachts to Rent in Chicago

Three of the specific types of yachts that you can rent in Chicago might include skiffs, catamarans, or sloops.


Skiffs are really good charter yacht options because they are small yachts that have room for about four people. They can be perfect for fishing and for family vacations. Skiffs with a shallow draft can reach more fishing destinations, including areas near the shore and backwater locations that can often hold plenty of fish.

Rent a Skiff


Catamarans are some of the best types of boats for hosting big crowds of people and when there is a lot of food and drink involved. Some perfect occasions for a catamaran rental on Lake Michigan might include weddings, birthday parties, or any other special types of celebrations.

Rent a Catamaran


Sloops are often easy to sail and they can also be very good party yacht options. Sloops are good boats for novice sailors to practice their yachting skills. Simply drop anchor and enjoy the best of the Chicago skyline.

Rent a Sloop

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