Discover Chicago, IL with Sailo - a gorgeous boating playground for you to enjoy!
Discover Chicago by private yacht charter with Sailo. Enjoy a whole other side of Illinois on a boat rental with captain, or skipper yourself if you prefer. Whatever your boating needs, you’ll find the perfect charter boat for your sailing trip, party or special event. Enjoy sunset cruises, watersports or fishing trips, or a day out with family and friends for a memorable experience on a Sailo boat.
Our premium Chicago, IL private boat rentals inventory
There are currently 15 Sailo yacht charters waiting for you in Chicago, IL. From a day trip on the water, to a week exploring (or more), it’s easy to find the perfect boat for you on Sailo. Our inventory includes 2 beautiful sailboats waiting to take you away. You’ll find 1 catamarans to charter in Illinois. If you prefer, in Chicago, Illinois you’ll also have the choice of 3 motor yachts for an unforgettable trip. Throw the party of the year in Illinois on the deck of your own party boat rental suitable for more than 13 guests: search the 9 options in Chicago with Sailo and book the one for you.
How to find the ideal yacht for unforgettable yachting experiences
Sailo has the most advanced filters to help you find the perfect boat rental for an amazing experience on the water in Chicago, IL. Start your search by choosing your start trip date, duration and number of guests. For a great day trip with your family or friends, you have the option to select 2, 4 hours or full day rentals. Depending on your preferences and budget, you may narrow your results by boat type and price range. The 'crew' filter allows you to check the boat rentals with the captain included in the price, skipper optional (paid as extra) or bareboats that you’ll captain yourself (boating resume required). Once you have laid your eyes on a boat you like in Illinois, click on it to read the description, reviews and see more pics. We also recommend using our direct 'Message Owner' feature that allows you to start a conversation with the boat representative to ask away everything you want to know before you submit a booking request.
How much is it to charter a Chicago, IL yacht for a day?
Whether you are looking to rent a yacht for a city sightseeing tour, a romantic sunset cruise or an active day on the water with your family or friends, we're confident you’ll find the best one for you on Sailo. The average starting price to charter a yacht in Chicago is $1100. You can however find excellent affordable rentals from $250 and also elegant yacht charters that can go up to $6500 (service fee and mandatory extras not included).
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