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Chicago, IL could be the ideal yachting playground for you

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 finest collection of party boat charters in Chicago, IL

Planning for a private event with your family or friends or a business occasion that you’d like to celebrate in a special way? Choose one of our top rated party boat rentals in Chicago, IL! 8 event boats with capacity of 13+ guests are available in Chicago, offering a variety of catering package options, entertainment and professional crews trained to make your special event unique and memorable. Rent a party yacht in Chicago, IL from Sailo: it’s easy, quick, secured and the best way to surprise your guests with an exclusive experience on the water!

Learn how to find the right boat for great yachting experiences

Wondering how to find the best charter for a memorable experience on the water in Chicago, IL? We have created a set of advanced filters to help you navigate easily our database of Chicago boat rentals and yacht charters, and find the one for you. First pick a start date and then choose your trip duration. You can go for an extraordinary of 2, 4 hours or full day experience. Next, select the number of guests, the type of boat and the price range you are comfortable with. The crew filter helps you narrow down the results to the boats with the captain included in the price, or bareboats that you’ll captain yourself. Choose the boat you want in Illinois, to view more pics, read description and reviews. Message the owner if you have any questions or continue with your booking request.

How much does it cost to charter a yacht in Chicago, IL?

Chicago, IL yacht charters for daily trips are available at an average of $1100 per day. Cheaper boats (sometimes with no captain included) may be rented for $250. Our Chicago premium charters may have price tags up to $6500, with crew, fuel, docking fees and other extras added to your budget.

Can I pay in installments for my Sailo boat rental?

A lot of our boat owners allow payment in installments, particularly for the weekly charters. First installment is always charged at the time the booking is confirmed. To find out if a boat has an installment plan, reach out to the boat representative and ask details via 'Message Owner' before you submit the booking or check out the Payment Schedule at top of the booking page.

Because we love the ocean

Sailing is a great way to experience nature. So we like to remind everyone that keeping nature as beautiful as possible involves a little effort from all of us. Some of our tips for responsible boating include:
  • Don’t litter or throw waste overboard - take rubbish home and dispose of it responsibly
  • Eco-friendly sunblock can help prevent damage to marine life
  • buy local and sustainable food products
However long you’re sailing for, a little goes a long way. Read more about responsible boating.