Sailboat Rental in Chicago

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With or without a skipper
0 - €1,200+
0 - 60+ m
0 - 400+ hp
Year of construction
2003 - 2024
Search radius (from starting port)
100 Max Km
Adapt your dates to find more sailboats and catamarans! 70% of these boats are charted from Saturday to Saturday.
2 sailboats available

Hunter Marine - Legend 35.5 | 1 cabin (1987)

With skipper

From €38 per day

See more nearby boats
These boats are available around Chicago, United States

Hunter - 33.5 | 2 cabins (1989)

Racine County
With skipper

From €1,361 per day

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Rent a Sailboat in Chicago for the perfect holiday

When most people think of Chicago, they think of a striking skyline, deep-dish pizza, and the local baseball team, the Cubs. But there is so much more to see in this Midwestern metropolis! If you're looking for a unique holiday experience that combines the best of both worlds - city life and water sports - then a sailboat rental in Chicago is the perfect option for you. Situated on the shores of Lake Michigan, Chicago is one of America's most vibrant and cosmopolitan cities, with plenty to see and do both on land and on water. What better way to explore the city than from the deck of your own private sailboat? With Scansail you can rent a sailboat in Chicago and enjoy the scenic waterway of the Chicago River or see the sprawling lakefront of Lake Michigan, a sailor's paradise, with many nautical miles of coastline to explore. What are you waiting for? Embark on a sailing excursion in the Windy City!

What is the cost of a sailboat rental in Chicago?

If you want to sail in Chicago, the price of a sailboat charter will vary depending on the time of year, how many people are onboard the vessel and the type of sailboat you choose. Of course, if you choose a sailboat with more amenities and services, the price will be higher. The average price of a sailboat rental in Chicago is about €9,527/week or €1,361/day for 6 people on board.

What is the best time of year for a sailing excursion in Chicago?

For the hottest weather, visit Chicago in summer when the average water temperature in Lake Michigan is around 22 °C. However, keep in mind that the average high air temperature is 35°C so if you're looking to enjoy some time on the water without feeling overheated, the best time to visit Chicago for sailing is in the spring or autumn.

Should I charter a sailboat with a skipper in Chicago?

Illinois law requires any person navigating a sailboat to have a nautical licence, but if you don't have a licence, that doesn't mean you can't enjoy the water!

If you're considering chartering a sailboat in Chicago but you don't have a licence to sail, don't worry, at Scansail we have many sailboat rentals which include a skipper and in some cases you can request a skipper at an additional cost.

There are many advantages to having a skipper onboard your sailboat rental. Firstly, you'll be able to relax and enjoy the ride, you won't have to worry about steering the boat or dealing with any of the other technical aspects of sailing - that will all be taken care of by your skipper. But the best part of having a skipper on board is that you'll get to see Chicago from a unique perspective, as most of the skippers are usually locals who can take you to see hidden gems you might not have known about otherwise.

What can you see and do with a sailboat rental in Chicago?

Here are just a few of the things you can see and do when you visit Chicago: 

  • Take in the skyline. Whether you're sailing on Lake Michigan or taking in a birds-eye view from the top of the Willis Tower, the Chicago skyline is truly something to behold. Visit one of the city's many museums. You'll find one of the largest museums in the world: The Field Museum, where you can learn about natural history and see the most complete T-rex that has ever been discovered. You can also see one of the oldest art museums in existence, the Art Institute of Chicago. No matter what you're looking to learn about, you'll find the perfect museum to suit your needs in Chicago.
  • Shop till you drop on Michigan Avenue. Also known as the Magnificent Mile, this stretch of Michigan Avenue is home to high-end retailers, department stores and more. Sample the city's food scene. From deep-dish pizza to loaded hot dogs, there's no shortage of delicious food to be found in Chicago.
  • Catch a game at Wrigley Field. A visit to Chicago isn't complete without catching a game at one of America's most iconic baseball stadiums. Located in the heart of downtown, this is a great spot for people who want to be close to all the action.
  • Try one of the many watersports available in the city! From stand-up paddleboarding to kayaking to kitesurfing and windsurfing, there's something for everyone to enjoy.

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