3 Sailboat Charters in Chicago, IL

Looking for a sailboat rental in Chicago, IL? Discover Chicago by a private sailboat yacht charter with Sailo. Enjoy a whole other side of Illinois on a sailboat rental in Chicago with captain, or skipper yourself if you prefer. Whatever your boating needs, you’ll find the perfect sailboat for your Chicago 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 inventory of private sailboat charters in Chicago, IL

Chicago, IL is a well-known boating destination in the US, perfect for a memorable experience on a Sailo boat. The sailboat rentals are popular for both locals and tourists and a great choice if you want to spend some quality time with your family or friends. 16 charters are currently available with or without captain, lined up in the Chicago’s marinas, waiting for their guests. Rent a private sailboat in Chicago with Sailo: it’s easy, quick, secured and the best choice for a fun experience in the waters of Illinois.

How to find the perfect Chicago sailboat charter?

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

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 yachting tips

If you’re looking to start Chicago sailing, a sailboat 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

Read more about responsible boating.

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