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"BIG BOAT" - up to 36 people
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Sailboat Rental Chicago

(see our Power Boats here)

Sailboat Rental Chicago vessel options:

All of our sailboats have fully functional marine heads (bathrooms), stereo systems, and plenty of cooler space for your drinks and food. Also, all of the boats listed below are owned by us, available for charter the entire season, which means that you can call us or use our online availability calendar to check availability immediately and not have to wait for 3rd party responses.

Click on any picture or title below to see more info on the specific type of boat.

Verloren, Khoya, and Missti
These are stylish 39′ luxury cruisers designed for a balance of comfort and performance. Because of this design, the seating area in the cockpit is larger than even most 40-45′ sailboats, and there is a great deal of deck space. As well as being comfortable, these sailboats do not lack in speed and handling. Able to sail in even the lightest of winds, as well as heavy conditions, these are perfect all around ships for Lake Michigan pleasure sailing.


This 36′ sailboat has nearly as much size as our luxury boats, and a comfortable cockpit that is also larger than most 40-45′ sailboats. Whether for a romantic sail for 2, or a larger group (we can comfortably carry 8 for large group rentals), our Large Class will deliver a great sail.


This 31′ Sailboat has more room in the cockpit and down below than most boats it’s size due to its 11′ “beam” (width). Though we frequently sail with 6 guests on board, if you are looking for true luxury we suggest one of our 36′ or 39′ cruisers above.
Other boats that we can occasionally book for you range from 30 – 42 feet, and various styles. If the above sailboats are unavailable, we may suggest one of these for your group. Please feel free to contact us with any questions you may have about the boats or anything else.
Chicago Sailboat Charters   773-236-7245