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Chicago, IL could be the perfect boating playground for you

Well known for its stunning location, Chicago is just crying out for you to discover its hidden gems with a sailboat, catamaran or motor yacht rental. Rent a boat with Sailo in Chicago, and you’ll be able to enjoy the local scenery at its best. Take your time and unwind on the deck of your own private boat with captain, or take the helm and enjoy the thrill of being on the water on a bareboat charter in Illinois.

Our finest inventory of private yacht charters in Chicago, IL

Explore the beauty of Illinois state from Chicago with a yacht charter. You’ll find 16 boats to rent in Chicago with Sailo, for the best choice. Set sail on one of our 1 elegant sailboats. You can also choose from 1 catamarans, available to charter. What better way to discover the shores of Illinois than from the deck of a luxury motor yacht? Browse the 4 available on Sailo for your ideal boating trip. You’ll also find 10 larger party boats, perfect for groups of 13 or more available in Chicago, IL.

Learn how to find your yacht for extraordinary boating 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.

Essential safety tips for recreational boating

Whether you’re renting a boat with captain or you choose a bareboat, always keep in mind this basic safety guidelines:
  • if you rent a captained charter, always pay close attention to your captain
  • walk slowly and never run onboard as you can easily slip and fall overboard
  • be mindful of stairs and hatches (never step on them)
  • if you go swimming, floating or paddling, stay away from other boats even if they are anchored or moored
  • pay attention to the other group members and make sure that everybody is accounted for at all times

Sustainable boating tips

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.