Enjoy a one-of-a kind experience on the water in Downtown Chicago, IL with your own private Sailo yacht charter. Whatever your sailing style; from experienced skipper, fishing fanatic or thrill seeker, to those who just want to relax on deck with your family or friends, you’ll be spoiled for choice. Rent a boat in Downtown Chicago, IL with Sailo for a memorable day trip or a sailing vacation to remember.

How to find the ideal yacht for unforgettable yachting experiences

Sailo offers beautiful boat and yacht rentals at various price points in Downtown Chicago, IL. Use our advanced filters to narrow your search by date, group size, and trip duration: 2 hrs, 4 hrs or full day charters. You can also choose the type of boat (sailboat, motorboat, catamaran) you want and go even further and look for a particular length, manufacturer and model. The price filter will help you see the available boats within your budget and the crew option is useful when you want to see boats with a skipper/captain included or only bareboats. Do you see a boat that you would like to rent in Downtown Chicago, IL? Click on it to go to the next page to read more about it, see more photos, send a direct message to the owner to ask more questions or start creating your booking request right away!

How much is it to rent a yacht in Downtown Chicago, IL?

You can charter a boat for a day in Downtown Chicago, IL for an average of $1100 per day. The average price for a weekly boat rental is $3500. Your total budget for a boating trip in Downtown Chicago, IL depends on many factors such as: trip duration, if captain and crew are included in the price or their cost have to be paid separately, fuel cost (which could be significantly higher on a motorboat compared to a sailboat) and other extras you choose to customize your experience in Downtown Chicago, IL.

What is Sailo’s cancellation policy?

As long as the booking request hasn't been accepted by the boat owner, the renter can cancel the request without any charge. If the renter cancels after the booking request has been accepted, the booking will be subject to the terms of the cancellation policy in place for each boat. The renter should check the cancellation policy with the boat owner, as some of the professional operators have specific cancellation policies which supersede that of Sailo. Whenever a boat owner doesn't have a specific cancellation policy,Sailo's Standard Cancellation policy will apply.

Guidelines to responsible yachting

If you’re looking to explore our beautiful planet, a yacht charter is a great place to start. Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto: 'Take only photos, leave only wake' (OK, so we paraphrased). To be a responsible sailor, remember:

Don’t disturb coral or sealife
Take your trash home (and don’t throw anything in the sea)
Respect the locals and their customs wherever you go