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19 Boat Rentals & Yacht Charters in Chicago, IL

1 - 18 of 19 boats

Rent a Luxury Yacht Charter in Chicago, IL with Sailo!

Choosing a luxury yacht rental in Chicago, IL? Enjoy the freedom of the open water on a private boat rental in Chicago, IL from Sailo. Rent a boat from a couple of hours to a full day, to really explore Illinois from Chicago. With a licensed captain driving your boat rental with, you’ll be able to relax and discover those hidden gems with your friends or family. Prefer to skipper your yacht rental? Use our advanced filters to find your perfect bareboat charter on Sailo!

Our premium selection of private boat rentals in Chicago, IL

There are currently 15 Sailo Chicago yacht charters waiting for you in Illinois. 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 boats for Chicago sailing waiting to take you away. You’ll find Chicago catamaran rentals and charters in Illinois. If you prefer boating in Illinois you’ll also have the choice of Chicago motor boat rentals 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 Chicago party boat rentals with Sailo and book the one for you.

How to find the perfect boat charter for Chicago for sailing?

Sailo has the most advanced filters to help you find the perfect boat charter in Chicago for an amazing experience on the water in Illinois. 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 Chicago boat rental 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 does it cost to rent a yacht in Chicago 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 sailing is $1100. You can however find excellent affordable rentals from $250 and also elegant Chicago yacht charters that can go up to $6500 (service fee and mandatory extras not included).

Can I rent a boat in Chicago with a captain?

When you rent a Sailo boat rental in Chicago with captain, you set yourself and your guests for a relaxed, worry-free trip, with a professional skipper making sure that you all have an amazing experience on the water. Currently we offer 14 boat and yacht rentals with captain in Chicago for sailing.

Sustainable yachting tips

If you’re looking to explore our beautiful planet, a boat rental in Chicago 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

Read more about responsible boating.

Popular locations to rent a boat on the Midwest USA:

Popular boat types among renters: