Sailboat charter in Chicago

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With or without a captain
0 - $1,300+
Boat length
0 - 196+ ft
Boat power
0 - 400+ hp
Construction year
2003 - 2024
50 Max MI
Guests usually rent sailboats and catamarans from Saturday to Saturday. To receive the best options, adjust your search dates.
2 sailboats available

Sailboat - 10.82m — Hunter Marine - Legend 35.5 (1987)

With captain

From $42 per day

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These are our available boats around Chicago, United States

Sailboat - 10.06m — Hunter - 33.5 (1989)

Racine County
With captain

From $1,499 per day

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Sailboat charter in Chicago - Let’s sail Lake Michigan

Ocean Evasion gives you the opportunity to explore with a sailboat charter in Chicago. Explore the city in a different way onboard a sailboat. Lake Michigan is a great place to sail and get your very own personalized sailing experience. It is a great getaway experience, especially during the Spring, Summer, and Fall months! Each season has its own unique beauty to fall in love with Lake Michigan!

Our sailors at Lake Michigan will make your experience very memorable, taking you and your friends or family around the lake. The sailors at Lake Michigan are always very happy to share their passion for adventuring with a sailboat, entertaining new passengers and friends from Chicago, and exploring the water. Your sailboat rental in Chicago will bring you across Lake Michigan so you can admire both Chicago’s skyline and the different areas there are.

How much is it to rent a sailboat in Chicago?

The price of a sailboat charter in Chicago varies depending on the characteristics of the boat, the number of passengers, and if you’re choosing to rent with added services or if these services are already included by the boat owner. Each boat owner has a different listing in which they can choose their own prices and the additional services they would like to include.

The average starting price to charter a sailboat in Chicago is $1100. You can however find excellent affordable rentals,and also elegant yacht charters that can go up to $6500 (service fee and mandatory extras not included).

What is there to see in Chicago?

A sailboat charter in Chicago is the best way to make your trip turn into something special. One of Chicago’s best attributes, especially in the summer, is the huge ocean lake that sits right next to it!

In the summer, Lake Michigan is a must-visit! It becomes alive when Memorial Day hits with people from Chicago heading onto the water to boat, jet ski, or live it up in the summer. A sailing trip with your boat rental is a great way to spend your time in the sun! There are 24 free beaches to explore with your Chicago sailboat rental along with a nice long waterfront to view while sailing away.

Lake Michigan is also one of the 5 great lakes covering portions of Illinois, Indiana, Michigan, and Wisconsin. If you’re considering renting a sailboat in Chicago, think about how long you would want to stay on board! With these four states close by this could be your opportunity to set sail and explore all of the states connected to the great lakes!

However, the fun doesn’t stop there! A sailboat charter in Chicago can also take you through the Chicago River! Voyage through the city and check out the Chicago Riverwalk along the south bank which is dotted with buzzing bars, restaurants, and urban art. Why not ask your captain if they know more about the 50 iconic buildings on the waterfront? You can create your own full-day private boat tour where you can hear all of the stories behind these buildings!

Rent a boat with a captain in Chicago

Ocean Evasion lets you decide if your sailboat charter in Chicago is with or without a captain. Renting a boat with a captain is ideal if you don’t have the appropriate boating license for your sailboat rental in Chicago. This gives you the freedom to relax on board while someone else takes care of navigating you through the river and lake and all of its surroundings.

Likewise, you may choose to rent a sailboat in Chicago without a captain! This is also a great idea if you would like to practice navigating with your boating license and get that sailing adventure your heart desires. If you’ve always wanted to try driving a specific sailboat then this could be your chance!

Why rent a sailboat?

A sailing boat is an optimal choice for those who want to get into sailing. Sailboats are classically refined and contemporarily equipped with an unforgettable performance and comfort on board. This is where sailing tradition meets new adventure in places with your ability to go through Lake Michigan and the Chicago River.

You can use this sailing experience to bond with the people on board! Whether you are planning a romantic getaway with your loved one, a fun activity with your family or group of friends, or even a team-building event.

What is the best time to go to Chicago?

The two diverse weather conditions in Chicago make sailing time-limited. From November to April the weather gets cooler with highs of 59°F and lows of 18°F. In the summer months instead (from May to October), the weather gets warmer. The peak in July is 84°F, with the rest of the months ranging from 64°F to 83°F.

What are the sailing conditions in Chicago?

Check with the boat owner before setting sail about the sailing conditions during your rental period. An unexpected change in winds, seas, or visibility can reduce the efficiency of marine operations and make the ride not as enjoyable as it should be.

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