sailboats in chicago

ON A BOAT SAILING

Luxury sailing adventures along chicago's lakefront, what makes  on a boat sailing different.

If you appreciate attention to detail, hospitality, and thoughtful amenities, this is the group experience for you! Our Chicago sailboat charters & cruises have been enjoyed by thousands of guests since 2018. As we hit the waterfront for our 7th season, we pride ourselves on offering an unforgettable way to experience Lake Michigan from the City.

The Crew - Captain Greg & 1st Mate Cait

Our crew have a combined 25 years sailing experience, allowing us to curate the best possible experience for our guests. Sit back & relax as you take in the sights & sounds of Chicago's famous Lakefront.

The Yacht - 2003 Jeanneau Sun Odyssey 37

S/V Dragonfly was built for day cruises & entertainment. Our 37' luxury sailboat is a fantastic venue for any special occasion. We are a fully-licensed commercial passenger vessel and operate under the highest safety standards monitored by the US Coast Guard.

Learn more about our crew and yacht   here .

Whether you're getting on the water for the first time or a seasoned boater, our focus is to curate your special outing with world-class sailing, comfortable amenities, and incredible views of Chicago's famous Lakefront.

2024 bookings are available from Memorial Day weekend to mid-September with multiple departures daily from centrally-located Monroe Harbor in Downtown Chicago . Please visit our all charters page to learn more about our one-of-a-kind sailing adventures. Chicago is the best place to combine the thrill of sailing with views of a city steeped in rich architectural history - let us show you. Cheers! Captain Greg & First Mate Cait

OVER 500 PRIVATE CHARTERS IN CHICAGO SINCE 2018

Chicago sailboat  charters & cruises, limited weekend bookings available - book now, sail & swim playpen charter.

USCG Captain

Chicago's famous lakefront party is back! This 4-hour private sailboat charter is designed for you & your friends to party in luxury. We will depart from Monroe Harbor, with a good mix of adventure sailing on Chicago's Lakefront along with dropping anchor at the Playpen or a private area of your choosing. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!

  $1,399 | Up to 7 Guests  

Fri • sat • sun departing 10am & 2:30pm.

Navy Pier Fireworks Cruise

Uscg captain .

This 2.5 hour Chicago sailboat cruise will split your time us between sailing the city's famous Lakefront & eventually making our way to the famous Fireworks show at Navy Pier. These are the best seats you can possible have for a world-class fireworks show. We've all seen fireworks - you've never seen anything like this before.

$999 | Up to 7 guests 

Wed  7pm •   sat  8pm.

“I rented [Dragonfly] to celebrate my bday with 6 close girlfriends. Greg was very communicative before the trip. He answered all my questions in a very timely manner. The boat is very spacious!

Dyna, Chicago, IL

Chicago Lakefront Cruise

This 3-hour sailboat cruise will take you & your guests on a favorable sail down the gorgeous coastline of Chicago's lakeshore, giving a unique perspective on the city's world-class architectural landscape. If you're looking for a private & intimate sailing experience- this is the cruise for you.

$899 | Up to 7 guests

WED • FRI • SAT • SUN Departing 10am, 1:30pm & 5:00pm

Skyline Sunset Cruise

Relax and enjoy a captained sunset cruise on our sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off from Monroe Harbor in downtown Chicago and set sail to a favorable course on Lake Michigan. Bring your own food and drinks, listen to your favorite music, and take in the views of our city’s iconic skyline from the Lakefront.

$799 | Up to 7 guests 

FRI • SUN Departing 6:30pm

PLAN YOUR CHICAGO SAILING ADVENTURE  TODAY!

Explore world-class sailing, Great Lakes swimming & luxury amenities all summer long.

555-555-5555

[email protected]

OUR SPACIOUS, LUXURY

LUXURY SAILBOATS

When you rent a boat from chicago sailboat charters, we provide the best variety, service, and value for any charter or rental boat experience you desire..

12 PASSENGERS

FLEXIBLE BOOKING

BELMONT HARBOR

These are stylish 39′ luxury cruisers designed for a balance of comfort and performance. Because of this design, the seating area in the cockpit is larger than even most 40-45′ sailboats, and there is a great deal of deck space.

As well as being comfortable, these sailboats do not lack in speed and handling. Able to sail in even the lightest of winds, as well as heavy conditions, these are perfect all around ships for Lake Michigan pleasure sailing.

WHAT'S INCLUDED IN YOUR CHARTER

HOW TO BOOK YOUR CHARTER ONLINE

Step 1: Use our online booking platform (click HERE ) to select your date and view charter availability.

Step 2: Once you select your charter, reserve and pay directly online in less than 60 seconds.

Step 3: After booking, refer to your confirmation email for instructions on how to book a captain. 

WHY CHICAGO SAILBOAT CHARTERS?

Chicago Sailboat Charters offers Chicago's largest variety of captained charters for sailboats, yachts, and spacious boats, accommodating groups of 1 to 36 people. Enjoy daytime sailing, sunset cruises, swimming and sunbathing sails, or even witness the spectacular Navy Pier fireworks from our boats.

OUR SAILBOATS & YACHTS ARE PERFECT FOR...

Swimming & playpen, navy pier fireworks, chicago river cruises, celebration events, corporate outings.

773-236-7245

[email protected]

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400 West Belmont Harbor Drive, Chicago, IL 60657

Belmont Harbor

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Dusable Harbor

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How to rent a sailboat in chicago, find the perfect boat.

Enter your desired location and date to explore our fleet of sailboats.

Select a captain

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Book with ease

Connect with your boat owner and complete your booking online.

Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

Got questions?

Frequently asked questions

What makes Boatsetter different from other boat rental platforms?

What makes Boatsetter different is peace of mind. Boatsetter is the first and only boat rental marketplace to offer insurance on every peer-to-peer boat rental. We know choosing the right boat rental platform is essential to your experience while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

How to rent a boat on Boatsetter?

At Boatsetter, our mission is to make getting out on the water as easy as possible. With our intuitive booking system, you can rent a boat as soon as today. -First, you must determine your budget and the type of boat you want to rent. -Next, decide where you would like to boat and the kind of boat you would like to spend the day on. -Finally, determine if you will be needing a boat captain and reach out to the boat owner. That’s it! You’re officially on your way to a fantastic day out on the water.

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How much does it cost to rent a yacht?

The cost of renting a yacht depends on the boat’s size and the amount of time you’ll use the yacht. The onboard amenities and luxurious accommodations also dictate the price. You can contact our yacht specialists for a custom quote by visiting https://www.boatsetter.com/luxury-yacht-charters .

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

Can you rent a yacht for the day?

Boatsetter allows you to rent a yacht for the day. Single-day yacht rentals are available for a select number of yachts. To chat with a yacht specialist please visit https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the week?

Boatsetter allows its customers to rent a yacht for the week. Renting a yacht for a week gives you more access to the wide range of yachts available on our platform. You can either book a rental directly through the site or connect with one of our charter specialists to plan your trip here: https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the month?

Booking a month-long yacht rental is a detailed and hands-off process when working with our team of yacht charter specialists. We tailor each yacht charter to our client's specific wants and needs. Our luxury yacht charter specialists can be reached at (954) 715-4114 or by visiting https://www.boatsetter.com/luxury-yacht-charters .

How to rent a private yacht?

Renting a private yacht is a very detailed experience that caters to your exact needs while onboard one of our luxury yachts. To plan your private yacht rentals experience please visit https://www.boatsetter.com/luxury-yacht-charters .

How much does it cost to rent a pontoon boat?

The cost of renting a pontoon boat depends on the size, location, and rental time of the boat. Prices can range anywhere from $200 for a half-day rental or just under a $1,000 for longer rentals.

How much does it cost to charter a yacht?

The cost to charter a yacht varies depending on the boat size and the length of the charter. Prices typically range from less than $1,000 to $5,000 plus if you’re wanting to charter the yacht overnight.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.

How does the boat insurance work?

Boat insurance typically covers loss caused by things such as fire, sinking, storms, and collisions. The extent of the coverage varies depending on the policy.

Do I need my own insurance to rent a boat?

You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.

Does Boatsetter screen renters?

Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.

Is listing my boat on Boatsetter free?

Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!

What if I'm not comfortable having a renter drive my boat?

If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.

Top destinations for sailboat rentals

Top sailboat rentals reviews in Chicago, IL

Set Sail from...

Fantastic experience! We loved the attention to detail and extra effort in building is the best itinerary for our...

We had an awesome time out with Dawn and her husband for a sunset cruise during the week. We got lucky with a perfect...

Private Sailboat...

Jim and his crew were fabulous. We actually got upgraded to a nicer bigger boat too! They were very helpful to our...

Dawn and her husband were professional, fun and friendly. Our group had a great time!

We had an exceptional experience with our boat charter! As someone who had never booked a boat before, I didn't know...

We had a perfect day out on the lake!

Raymond was amazing! We had so much fun on the boat. I would definitely recommend using him for any sailboat...

Private sailing...

We had a great time! Thank you so much for everything 🙂

It was awesome, thank you so much Dawn! We enjoyed a lot!

Great communication! We will sail with them again.

Absolutely loved it! Dawn and her husband are truly amazing skippers and great to hang out with!

Sailboat Rentals in Chicago, IL

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A full service boatyard with certified technicians trained in an array of services. 

25 Acres in Chicago on the Calumet River with over 200,000 sf of indoor storage. 

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3434 East 95th Street, Chicago, Illinois 60617, United States

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2 seriously injured after boat hits breakwall near Chicago Playpen: CFD

CHICAGO (WLS) -- Two people were seriously injured Wednesday night, after the boat they were on in Lake Michigan hit a breakwall, Chicago fire officials said.

CFD responded to the 600-block of North DuSable Lake Shore Drive for the boat incident, fire officials said on X just after 9:50 p.m.

ABC7 Chicago is now streaming 24/7. Click here to watch

A boat hit a breakwall near the Playpen and Ohio Street Beach.

SEE ALSO: Diver's body recovered from Lake Michigan shipwreck in Kenosha County, Wis.

Two people from the boat refused medical treatment, but one was taken to a nearby hospital in critical condition, and another was in serious condition, CFD said.

It's not immediately clear why the boat crashed.

Video of the scene was captured by a Citizen app user.

Five ambulances responded to the incident.

In June, a 58-year-old man died after falling from a boat in the Playpen .

And, in 2022, a woman lost both her legs in a boating accident in the area.

This is a developing story; check back with ABC7 Chicago for updates.

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In addition to the best offers we have for boat and yacht charters in Chicago, IL, see also options available for rent in these nearby locations:

• 22 boat rentals in Chicago Loop, Chicago, IL
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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:

• Rent a boat in Detroit
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Popular boat types among renters:

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Watch CBS News

2 rushed to hospital after boat accident at Chicago's Playpen

By Jermont Terry

Updated on: September 12, 2024 / 7:04 AM CDT / CBS Chicago

CHICAGO (CBS) -- Two people were rushed to the hospital Wednesday night after a boat hit a breakwall in the so-called Playpen near Navy Pier.

At least four people were on the boat at the time. It was not clear if any of them fell into the water, or what happened to the captain of the boat who hit the breakwall.

Two people were taken to Northwestern Memorial Hospital — one in serious-to-critical condition and the other in fair-to-serious condition.

Two others refused medical treatment.

CBS News Chicago's cameras captured one person being loaded onto an ambulance.

The Fire Department called an EMS Plan 1 for five ambulances before it was clear how many people were injured. The Chicago Police Marine Unit was also called to the scene.

The Playpen is located between Oak Street Beach and Navy Pier and is popular with boaters in the summertime. A brick wall helps keep the waters calm while providing a backdrop of Chicago's skyline. 

Within the past couple of years, there have been a number of incidents at the Playpen. In June,  a man fell off a boat at the Playpen and died – his body was found four days later.

• Lake Michigan

Jermont Terry joined the CBS 2 team in October 2019. He's born and raised on Chicago's South Side. He's happy to return home to report on his community after 18 years of uncovering stories across the country.

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Boat crash in lake's Playpen leaves 2 hurt, 1 critically

About 9:10 p.m., wednesday paramedics responded to the 600 block of north dusable lake shore drive for the accident, chicago fire officials said..

Two people were injured in a boat accident Sept. 11, 2024 near the Chicago Playpen.

Sun-Times file photo

Several people were rescued during a boat crash Wednesday night in Lake Michigan’s Playpen on the North Side.

About 9:10 p.m., paramedics rescued four people, including two who were injured, when a boat crashed in the 600 block of North DuSable Lake Shore Drive, Chicago fire officials said.

One patient was taken to an area hospital in critical condition while the other was in fair condition, also taken to a hospital, the fire department said.

Two additional boaters declined to be taken to a hospital, fire officials said.

No further information was immediately available.

Boats cruise across the Seine in Paris Olympics Opening Ceremony rehearsal

Dozens of boats snaked along the seine river on monday in a rehearsal for the paris olympics’ unique opening ceremony., by jerome pugmire and tom nouvian | the associated press • published june 17, 2024 • updated on june 17, 2024 at 11:15 am.

Curious onlookers gathered on bridges as dozens of boats snaked along the Seine river on Monday in a rehearsal for the Paris Olympics' unique Opening Ceremony next month.

A total of 55 boats made the journey from Pont d'Austerlitz, named after a French military victory in 1805, to Pont d'Iéna, a stone's throw from the Eiffel Tower , the nation's most striking and best known landmark.

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Officials are confident that the near four-hour ceremony will run like clockwork on July 26.

“Six months ago we had like 10 minutes delay on the timing and today we are very close, almost to the second to our targets,” Thierry Reboul, the executive director for ceremonies said. “So it is very satisfying. We’ve respected an extremely precise level of timing.”

On the day of the eagerly-awaited event, around 200 Olympic delegations will join the parade on more than 80 boats. They will make the journey from east to west, along a six-kilometer (3.7-mile) route which has become a major talking point — for its audacity as a unique open-air event and for its exposure to potential danger.

Security concerns  led French President Emmanuel Macron to say in mid-April that the ceremony could shift to Stade de France if the threat level was too high. But Reboul said Monday that authorities are preparing for the big day as originally planned, with no alternatives being prepared at this stage.

There will be a final rehearsal, involving the full armada of boats, before the Opening Ceremony — one which is expected to bring 100 world leaders to the city's embankments, where more than  300,000 people  will watch.

“We will give our heart and souls to make it a great success for the French people,” France’s Sports Minister Amélie Oudéa-Castéra said Monday. “They deserve it.”

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The rehearsal saw 10 police speedboats shadowing the convoy, as well as speedboats equipped with television cameras. There were armed police officers stationed at various points along the way. The boats crossed 16 bridges, passing by iconic landmarks such as the green-tinged Grand Palais — where fencing and Taekwondo events will be held.

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On each bridge, a few dozen people watched attentively.

“Fifty-five? That’s a lot of boats,” said 49-year-old Rosa Gabriel. Taking a break between walking from the Louvre and Notre Dame Cathedral, she watched it from the Pont des Arts bridge — fondly known as Love Lock Bridge, with its thousands of personalized locks attached to the railings.

One tourist even mistook the scene for something else.

“Maybe they are making a movie," said Driss El Kaoutari, a 42-year-old from Morocco who was on vacation in Paris with his daughter.

What people actually saw were empty vessels bobbing slowly by. But they will be full of life, color, sound and movement next month.

“You will have many delegation members on the boats with their uniforms and their flags,” Reboul said. "Around them there will be many other things, as you can imagine.”

The water itself has become a sensitive and thorny topic for the organizers and politicians heading into the July 26-Aug. 11  Paris Games . A whopping  $1.5 billion investment  has already been made to improve the Seine's water quality, with Macron and Paris Mayor Anne Hidalgo both promising to take a dip.

This time, it was Oudéa-Castéra's turn to give assurances about the river — where marathon swimmers and triathletes are set to compete during the Olympics.

She bristled a little when answering.

“Regarding the quality of the Seine's water, we are confident. You shouldn't ask us to be ready ahead of time,” Oudéa-Castéra said, adding that a new center for collecting waste will be opened next week.

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