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Renting a yacht in Chicago, IL - an unforgettable experience!

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.

Top private sailboat charters in Chicago, IL

Are you looking for a sailboat to rent in Chicago, IL? We’ve got your covered with a total of 14 waiting for you at the dock. Available with or without captain, these amazing charters are the best way to enjoy the coastal scenery during the day, a breathtaking sunset or a day full of fun in the water with family or friends. Rent a private sailboat charter in Chicago and get ready for a great experience in the waters of Illinois.

Learn how to find the best boat for you

Choosing the perfect Sailo boat for you in Chicago, IL is easy and quick thanks to our advanced filters! First we recommend filtering by date and trip duration. Whether you look for a 2, 4 hrs or a full day rental in Chicago, the group size is very important, as well as the type of boat you want for your adventure in the waters of Illinois. Use the price filter to see only options according to your budget and click on the 'Crew' button to choose if you want a boat with a captain or you want to drive it yourself (option Bareboat). Once a Chicago charter catches your eye, click on it to see the boat page with more photos and a detailed description. Check the reviews and send a direct message to the boat owner to ask more details!

How much does it cost to rent a yacht in Chicago, IL for a day?

Boat charter prices in Chicago, IL vary significantly. You can find great budget friendly rentals starting from $250 for a daily trip. Luxury or party yacht rentals for the day can cost up to $6500 where service fees and mandatory extras are not included. Your budget per day will vary depending on whether you are renting the boat in Chicago with captain and/or crew, fuel cost, special requests for pick-up and drop-off or other special arrangements you may want to make with the owner.

What should you pack when you go out on the water?

No matter if you are going on a day trip or on a week-long vacation, these are the essentials you should always make sure you have when you’re on a boat:
  • Sunscreen - make sure to reapply after you’ve been in the water!
  • A hat or a cap that fits you tightly and protects you from the sun
  • A jacket or long-sleeve sweater, preferably with sun protection (UPF)
  • Sunglasses
  • A change of clothes (just in case you get wet)

Responsible boating guidelines

However long you’re on a boat, it’s always a thrilling and fun experience. Here at Sailo, we like to make sure that the stunning beauty of the seas, lakes and rivers of our planet stay as pristine as possible. If you’re going to charter a yacht, from a few hours to week, try to follow these sustainable boating tips:
  • Take your rubbish home
  • Use eco-friendly sunblock
  • Avoid single use plastic
Much of the world’s plastic ends up in the sea, so reduce, reuse and recycle. Read more about responsible boating.