private sailboat charter chicago

START YOUR Chicago sailing adventure today!

The salty dog sailing co..

Since 2015, The Salty Dog Sailing Co. has been a premier provider of private Chicago sailing charters.

Whether you’re new to town, just visiting or a Chicago native, we invite you aboard “ Peony “, our acclaimed Dufour 325 Grand Large , to experience the serenity, joy and excitement of authentic Lake Michigan sailing.

Renowned for fine lines, ease of sail, and polished interiors, the premium Dufour brand is synonymous with luxury and high-quality craftsmanship.  Customized with an array of performance features, Peony delivers an unparalleled sailing experience with your comfort and safety as our highest priorities.

We welcome you to click “ Book Now ” to start planning your private Chicago sailing adventure today!

All Charters Are Private Events

Charter rates.

2 Hour Charter w/Paid Captain

Just for Fun with a Friend

Great for a Date / Proposal

Free Harbor Parking

Best Value for Group Size

Perfect Size for Summer Fun

Spread Out and Enjoy

Big Family / Party Size

Please Contact Us!

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.

Luxury Yacht Charters

Available in Chicago

Welcome to MERIDIAN PRIVATE YACHTS

Meridian Private Yachts is Chicago’s premier, luxury yacht charter company. Our philosophy is to build on dreams by creating the ultimate yachting experience. Enjoy exceptional views of Chicago in our luxurious fleet of yachts.

Booking a yacht is easy

Search for your desired destination, yacht package, and other related services.

Choose from our various yachts available for your use.

Confirm all of the details – and enjoy a unique yacht charter experience!

FEATURED YACHTS

Rose marie 47′ carver.

12 passengers

View Details Virtual tour available

Pier Pressure 47′ Carver

View Details

50′ Sea Ray – Nauti Nate

50′ sea ray – janell, checkmate 62′ azimut, what our clients say.

Mayra Lyssette Fernandez 47” Carver – August 2021 Meridian was the best experience for my son. We celebrated his 18th birthday with his closest friends. It was truly amazing how management made sure his friends were safe and comfortable. The music quality was impeccable and all the water toys available were unexpected. This cruise party was absolutely perfect. I will definitely return back to book again.

Leslie B. 50” Sea Ray – July 2021 We had the best time with Meridian Private Yachts! Gia was great at communicating and coordinating everything. Our captain was Ken and he was amazing! The bachelorette had the best time and so did our party of 12! Would highly recommend them!

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Meridian Private Yachts 312-348-6060 [email protected] 3155 S. Lake Shore Drive Chicago, IL 60616

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• Family Trips
• Bachelor Parties
• Marriage Proposals
• Photo Shoots
• Corporate Events
• Play Pen Cruises
• Fireworks Cruises
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All Private Yacht Charters

offered by Windy City Sailing

Anniversary Charter

Spend an unforgettable anniversary on board with Windy City Sailing. Our team is dedicated to giving you and your loved one a private charter sailing experience like no other. Witness the sunset while taking in the spectacular views of Chicago, the firework show of Navy Pier from the lake, or simply take the opportunity to enjoy one another's company while peacefully sailing.

Birthday Sailing Charter

If you're looking for an exciting way to celebrate your birthday, look no further than a private birthday sailing charter. Our professional crew will take care of every detail, leaving you free to enjoy the beauty of the Chicago sunset or fireworks show with your friends. A sailing cruise is the perfect way to make sure your special day is remembered for years to come.

Bareboat Charter

Have a larger gathering? You can experience Chicago's majestic skyline with the luxurious touch of sailing a private yacht! Bareboat Chartering, also known as Demise Chartering, can accommodate up to ten people, and you provide your own food and drinks. Start planning your excursion and make it an unforgettable memory.

Client Charter

To make a lasting impression on your clients, consider taking them on a client charter or company cruise. Doing so ensures that you don't take them to a crowded, noisy restaurant or sporting event. It is an effective way of conveying to them that you prioritize their time and are serious about your business. Our charters along the Chicago Lakefront offer unparalleled privacy and comfort. Show your attention to detail and sophistication with a memorable cruise.

Bachelor or Bachelorette Sailing Charter

Celebrate your bachelor or bachelorette party with a sailing adventure aboard Windy City Sailing! Make lasting memories and explore the picturesque shores of Chicago from the decks of the Nebula yacht. Indulge in the tranquility of the lakefront or use it as the perfect place for a grand celebration; the choice is yours!

Proposal Charter

Making a proposal an unforgettable memory is something both of you will cherish for a lifetime. Experience a romantic occasion by taking a private proposal charter from Windy City Sailing. You can create an amazing backdrop of the gorgeous Chicago skyline or bask in the color of bursting fireworks for a spectacular atmosphere. And if you desire a more intimate setting, the options of morning, afternoon, or evening excursions can help you make your proposal one to remember.

Special Event Yacht Charters

4th of July Sailing Charter

Each year, the Fourth of July Sailing Charter gives the citizens of Chicago the chance to witness some of the nation's most spectacular firework displays from the comfort of a boat. The tour has become increasingly popular and is one of the highest rated Independence Day activities.

Chicago Air Show Charter

Chicago Air and Water Show is a remarkable event that has long been captivating city dwellers. By taking a sailboat charter from us, you can experience the show from the lakefront. You won't need to fight the crowds for the best view, as you will be luxuriating on your yacht with an unparalleled outlook of the show.

Navy Pier Firework Charter

During summer, the Navy Pier gives us breathtaking firework shows. For an unforgettable experience, there is no better way to appreciate these amazing visuals than to charter a yacht . Our dedicated captains and crew members make sure that all your needs are taken care of, so you don’t have to worry about anything else. With our exclusive amenities, it is not even worth considering any other way to view these displays.

Choices Charters ​

Experience Chicago on the Water

Choices Charters Luxury Yacht Rentals

Experience elegance at its finest. .

The Choices Charters invites you to cruise with us along the beautiful blue waters of Lake Michigan and the Chicago River. Join us for private trips, spectacular views and unforgettable memories on a private yacht of your dreams! We are here to give you the very best boating experience possible by exceeding your expectations. 

ROMANTIC DINNER CRUISE FOR TWO

A private boat dinner is the epitome of romance and luxury combined into one perfect evening. Imagine dining on a private yacht with a perfectly painted Lake Michigan sunset as your backdrop, your favorite song playing in the background, and gourmet food prepared by our Signature Chef Kathryn’s Soul. Kathryn's Soul's Catering has a romantic all inclusive menu designed to suit your every taste and need, with the option to cater to special diets. Catering is sold separately.

Our Rental Experiences

Dockside Bed & Breaksfast

Dockside Rental

Romantic Dinner Cruise for Two

Iconic Lakefront Cruise

Wednesday Morning Sunrise Retreat

Signature Dining Experience

Lake Michigan Sunset Cruise

Navy Pier Firework Cruise

Just Chill'n

Captain Ed is a US Coast Guard Certified, Licensed Captain. He is a Navy Veteran (Viet Nam Era). He has been boating for over 15 Years. His love for being on the water has led him to desiring that others experience the beauty and serenity of the Sea. Choices Charters is the result of Choice. Captain Ed strongly believes that “The Choices we make, dictate the lives that we lead.”  thus, the name of his boat and his desire to expose others to the beauty of the boating lifestyle.

Kathryn’s Soul

Kathryn Miles, chef and owner of Kathryn’s Soul. Her love for cooking and baking started at the very young age of 10. Her father noticed that she had a gift for cooking, so he began to encourage it.

In 2019, Kathryn decided to take a chance and pursue her passion. Kathryn’s Soul, a restaurant that offers quality comfort food made with love was born.

"The choices we make, dictate the lives that we lead."

From the city to the shore.

TESTIMONIALS

GREG & MARIE

Every summer, I have the perfect  getaway on the Choices Charter! Sitting on the dockside is just enough for me to enjoy the Chicago Skyline and Lake Michigan.  

My first week in Chicago, I was able to set sail with my  friends for her birthday with Captain Ed. The combination of a relaxed atmosphere and impeccable service was perfect.

OTIS & CHANTI

We had the best time with Choices Charters! Captain Ed was very  accommodating ! This was our  first  time on a private  yacht.   We highly recommend!

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]

MAILING ADDRESS

400 West Belmont Harbor Drive, Chicago, IL 60657

Belmont Harbor

Directions →

Dusable Harbor

Yachting in Chicago, IL

Charter a yacht in Chicago to discover the allure of yachting amid the iconic skyline of the Windy City. Situated on Lake Michigan, Chicago offers a unique yachting experience, from cruises along the Chicago River to breathtaking views of the city's architecture. Explore the fusion of urban charm and waterfront elegance as you enjoy a luxury yacht charter in Chicago.

38' Meridian

47' Carver

54' Sea Ray

45' Azimut Atlantis

51' Sea Ray

32' Wellcraft Martinique

35' Sea Ray

38' Sea Ray

40' Formula

50' Sea Ray

55' Prestige

45' Prestige

48' Sunseeker Portofino

60' Sunseeker Predator

60' Sea Ray

60' Sea Ray Fly

40' Sunseeker

Why charter a yacht in chicago, il, family-friendly activities while yachting in chicago, il, explore chicago’s hidden spots with a luxury yacht charter, .css-1uazooj{display:-webkit-box;display:-webkit-flex;display:-ms-flexbox;display:flex;-webkit-align-items:center;-webkit-box-align:center;-ms-flex-align:center;align-items:center;width:100%;outline:2px solid transparent;outline-offset:2px;transition-property:var(--chakra-transition-property-common);transition-duration:var(--chakra-transition-duration-normal);font-size:1rem;-webkit-padding-start:var(--chakra-space-4);padding-inline-start:var(--chakra-space-4);-webkit-padding-end:var(--chakra-space-4);padding-inline-end:var(--chakra-space-4);padding-top:var(--chakra-space-2);padding-bottom:var(--chakra-space-2);padding:10px 16px;}.css-1uazooj:focus-visible,.css-1uazooj[data-focus-visible]{box-shadow:var(--chakra-shadows-outline);}.css-1uazooj:hover,.css-1uazooj[data-hover]{background:var(--chakra-colors-blackalpha-50);}.css-1uazooj[disabled],.css-1uazooj[aria-disabled=true],.css-1uazooj[data-disabled]{opacity:0.4;cursor:not-allowed;} .css-1pkhz46{font-size:var(--chakra-fontsizes-sm);font-weight:600;-webkit-flex:1;-ms-flex:1;flex:1;text-align:left;} how do i book a yacht on yachtlife .css-g5ledl{width:1em;height:1em;display:inline-block;line-height:1em;-webkit-flex-shrink:0;-ms-flex-negative:0;flex-shrink:0;color:currentcolor;vertical-align:middle;font-size:8px;}, when is my payment collected is it refundable.

Once you confirm your reservation, your broker will process your payment.

• If you are booking for a single day and your reservation is confirmed more than 7 days in advance, a deposit of either $1,000 USD or 50% of the total cost of the reservation (whichever is greater) is processed immediately in order to hold the yacht. Once your embarkation date is 7 days away, the remainder of the amount due is processed.
• If you are booking for a single day and your reservation is made 7 days or less in advance, the total price of your reservation is processed immediately.
• If you are booking for a multi-day charter and your reservation is confirmed more than 30 days in advance, a deposit of 50% of the cost of the yacht is processed immediately in order to hold the yacht. Once your embarkation date is 30 days away, the other 50% is collected for the price of the yacht, plus the APA, plus the taxes due.

Terms of refunds are dictated by the Charter Agreement. Generally, once a payment is collected, it is non-refundable. In certain circumstances, as dictated by the Charter Agreement, credits can be provided so you will be able to enjoy your yacht charter at a future date that is convenient for you.

Why is there a 3% credit card convenience charge?

Are my payment details saved on the app, what if your servers get hacked is my payment information really safe.

☀️ Now Accepting 2025 Membership Applications ☀️

Chicago's #1 Boat Rental

Book your boat. set sail. make memories..

Knot My Boat Charters is a Chicago boat rental company that specializes in yacht rentals, memberships, and corporate events for up to 12 passengers. Offering 17 iconic vessels from 33 sport cruisers to 70’ luxurious yachts, our team brings over 20 years of boating and hospitality experience, providing the best boat rental experience in Chicago.

Featured Vessels

Starting at $200 / hr, each boat rental comes equipped with upgraded audio, bluetooth, USCG safety equipment, and a kitchen, restroom, and cooler for guests to enjoy.

How To Book Your Charter

SELECT YOUR DATE

View charter availability on our booking platform

BOOK YOUR BOAT

Reserve and pay online in 60 seconds or less

HIRE YOUR CAPTAIN

Refer to confirmation email to hire a captain (fee not included)

Chicago Boat Charters

Why Knot My Boat Charters

Whether you're planning a social gathering, bachelorette/bachelor party, birthday, or corporate event, the Knot My Boat Charters team will provide you the best boat rental experience in the Chicagoland area!

When you book with us, the KMBC price includes fuel, tax, cleaning, safety training, and all of our amenities. We also supply you with a list of pre-approved captains that are familiar with KMBC vessels.

We dock at the 31st Street Harbor, Chicago's newest addition to the harbor system, providing an exceptional experience for you and your guests.

 Why knot book with us?

Corporate Packages

Impress clients or reward employees with corporate yacht charters in Chicago. Choose from luxurious vessels and customize itineraries to create a memorable boating experience. Enjoy stunning views, exceptional service, on-site catering, and a unique opportunity to bond outside the office.

Yacht Membership

KMBC members share all of the benefits of boat ownership for less than 1/3 of the cost of actual ownership without any of the hassles of maintenance, cleaning, storage, mortgages, or unexpected fees! Starting as low as $3000 per person, memberships are the economical option for guests interested in boating multiple times per season. 

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Can’t say enough good things about Knot My Boat Charters!! We had the best captain which made it such a good day on the water. Highly recommend to anyone looking for the best boating in Chicago!

KMBC was amazing to work with. The team is extremely knowledgeable and very accommodating. They had an extensive list of captains to choose from. I would highly recommend KMBC to everyone!

I’ve booked Knot My Boat Charter for my birthday the last 3 years and already booked my boat for next year during their Black Friday sale. Easy to work with and their captains are great. Highly recommend!

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Knot My Boat Charters is perfect for...

A yacht charter is the perfect way to create a memorable and unforgettable experience for your team. Learn more about corporate discounts.

Hosting a proposal or wedding party on a boat offers a unique and romantic setting that will create a memorable and intimate experience for you and your guests.

Hosting a party or birthday celebration on a boat provides a unique and fun atmosphere with stunning views and customizable itinerary, making it a memorable experience for your guests.

Bachelorettes

Tying the Knot? Host your bachelorette party on a boat in Chicago for a unique and fun experience with customizable itineraries, onboard amenities, and stunning views.

Family Gatherings

Hosting your family on a boat for the day is a unique and exciting way for families and kids to bond on the water. KMBC is family friendly, accommodating all ages.

Travel & Tourism

Visiting Chicago? Tour the Chicago skyline over the lake or via the Chicago river and experience the ultimate beauty of Chicago  during the summer.

Sign up to receive exclusive offers & future discounts!

Get ready to stay updated on all our latest news!

Chicago Yacht Membership: Discover Stress-Free Boating

2024 Chicago Boating Events & Activities

Your Ultimate Guide to Chicago Boat Rentals in 2024

“This was the best boat charter in Chicago! The captain and crew were fantastic. Great proximity to downtown and easy loading on and off. The boat rental in Chicago was a great price for everything.”

“I was referred to Knot My Boat for an upcoming bachelorette party. I spoke with one of the owners Sommy and he was really helpful in working out the details. Overall a very easy booking process, 10/10 would recommend!!!”  

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Weather & Cancellations

Frequently Asked Questions

(312) 971-0971

[email protected]

Dock Address

3155 S Lake Shore Drive Chicago IL 60616

Corporate Office

350 N La Salle St #420 Chicago, IL 60654

The information on this website is for general information purposes only. Nothing on this site should be taken as professional advice for any situation. By using this website you agree to our privacy policy, terms & conditions, and cancellations policy.

All Rights Reserved | Knot My Boat Charters, Chicago, IL

• Searay sundacer 35′ powerboat
• fireworks-sunset-cruise-wed-sat-nights
• Wheather Links

Testimonials

• Map of Chicago

Chicago's Best Boats and Yacht Charters

We have two of the best private charter party boats in chicago.

We offer two beautiful powerboats that can take a total of 25 people out together on Lake Michigan. A 51′ Searay Sundancer and a 35′ Searay Sundancer boat that can accommodate a lot of guests. We can bring both of our boats together so you and your entire group can do a “Tie-Up in the Playpen”. Summer in Chicago without spending time with all your friends in the Playpen should not be missed. Please book your group trips early before we get all booked up

Charters can range from going to the world-famous “playpen” where we can anchor and crank up the sound system and go for a swim or chill on our rafts to cruising along the lakefront and by navy pier. you can also take a trip through the “locks” and down the chicago river or some blue water cruising past the chicago lighthouse, the cribs of chicago, and into the deep blue waters of lake michigan and taking in some of the best views of chicago.

Chicago Sailboat and Yacht Charters provide our guests with exclusive, private charters that offer complete luxury, flexibility, and customization. Take your friends & family on a cruise and experience Chicago like you never thought was possible a priceless adventure.

On wednesday & saturday nights we offer sunset & fireworks cruises just off of navy pier., experience firsthand the relaxing beauty of a peaceful sail on our 4+ hour and all day private boat charter. boating in chicago is the perfect way to end the day with friends. maximum of 12 guests on a boat., come enjoy the beauty of chicago in the lap of luxury. our lake michigan boat charters include many points of interest around chicago such as: the playpen, navy pier, chicago river locks, chicago lighthouse, adler planetarium, shedd aquarium, soldiers field, buckingham fountain and many more., chicago yacht rentals - a unique way to explore the city, our cruises are perfect for these special occasions:.

• Bachelorette or Bachelor Parties
• Anniversary Cruises
• Special Occasions Cruises
• Chicago Scene Boat Party
• Birthday Parties
• Corporate events
• The World Famous “Playpen” we anchor, turn up the music, crack open the drinks and dive into the water
• Chicago River Cruise – Hanging out at City Winery
• Chicago Air & Water Show (Friday, Saturday & Sunday middle of August)
• Holiday Weekends (Memorial Day, 4th of July, and Labor Day- Book early they book up fast)
• Lollapalooza- Listening to the concert from Monroe Harbors

51′ Sea Ray

You can also find our website at BoatCharter.info

35′ sea ray.

Private, Luxurious, and Affordable Yacht Charters in Chicago, IL

Bring a group to party in the playpen, the playpen - chicago's popular boating place.

The luxurious amenities on our boat will amplify your experience as you feel the breeze blowing through your hair. The dazzling blue waters are ideal for swimming, and you can even climb aboard a floating island to take a break from all the action.

Whether you’re looking for some relaxation or some excitement, the Playpen is the ultimate destination for boating enthusiasts.

Chicago Sailboat and Yacht Charters Offer Priceless Pampered Yachting Experiences

At Chicago Sailboat and Yacht Charters, we pride ourselves on providing our guests with priceless, pampered yachting experiences. We go above and beyond to offer complete luxury, flexibility, and customization, tailoring each of our charters to your unique desires. From taking a cruise down the Chicago River to partying in Lake Michigan’s Playpen to watching the sun go down over the city, our yacht charters will help you do it all in style. At Chicago Sailboat and Yacht Charters, we believe that our guests deserve the absolute best, and we promise to deliver unforgettable, priceless yachting experiences that you’ll treasure for years to come.

WHAT PEOPLE SAY ABOUT US

Check out the Testimonials page to see what people are saying about our boat charters.

The views of the Chicago skyline were amazing, we can't wait to go again!

The captain made our trip really fun and educational seeing all the different sights like Navy Pier with its flags flying high was incredible and the views of the Chicago Lighthouse and water Intake cribs up close were amazing.

Our family had an incredible time sailing on Lake Michigan

The Fireworks by Navy Pier were incredible especially watching while having dinner and a good beer

(312) 587-3474

1300 s linn white dr, chicago, il 60605, contact/directions, chicago sailboat and yacht charters ©2023 all rights reserved.

CHICAGO BOAT & YACHT RENTALS  

Welcome Aboard!

PRIVATE YACHT & BOAT RENTALS For groups up to 13 passengers

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How to Plan your Boat Rental:

Book a boat.

You can book your Chicago boat rental online here . Start by selecting your date. You'll be able to select your boat and see capacity, rates and availability.

Captained Boat Rental

Shortly after you book you will receive a captain contact list of qualified captains who are familiar with our boats. We recommend budgeting $100/hr for the captain. See more info about hiring a captain for your boat cruise  here.

Prepare for your outing!

Refer to our FAQs here or reach out with any questions. Get ready to enjoy your power boat rental on Lake Michigan!

@chicagoyachting

1ST CLASS CHARTERS CHICAGO

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CELEBRATING 5 YEARS WITH CHICAGOLANDS' MOST UNIQUE CRUISING CATAMARAN! CELEBRATING 5 YEARS WITH CHICAGOLANDS' MOST UNIQUE CRUISING CATAMARAN!

Our 6 passenger Private Cruises are  the perfect escape from busy city life .

START YOUR NEXT ADVENTURE WITH 1ST CLASS CHARTERS

LET US SHOW YOU THE JOY SAILING CAN BRING!

We believe in creating a safe and memorable experience for our passengers. Whether you’re desiring a Chicago sightseeing tour on Lake Michigan, a gathering of friends and family, a corporate outing with preferred clients or a celebration of upcoming nuptials, planning with us has never been easier.

OUR SERVICES

6 person private cruises.

Relax with friends or family on your private cruise.

Captain is included with

6 Person Pricing

SEPTEMBER SPECIAL! PURCHASE ANY 2 HOUR CHARTER AND GET 1 HOUR FREE!

Take advantage of end of Summer savings!

Book any 2-hour sailing package at our regular rate, and receive an additional hour of sailing absolutely FREE!

Create cherished memories with friends and family, celebrate a special occasion or take out your preferred clients or show your employees your gratitude.

Join us this September and take advantage of our special offer, and let your sailing journey begin.

Save $450 on our up to 7 person charter or $550 on our up to 13 passenger Bareboat Charters.

Don't let this opportunity sail by!

Email or Call today.

12 PASSENGER CHARTERS

Party on Lake Michigan with up to 12 of your friends!

Charterer Must Hire Captain with more than 7! (USCG Rules)

List Provided

NEW FOR 2024 SPECIAL MULTI-CHARTER PRICING

To Celebrate our 5th Year in Business

We are Offering a Special Deal

4 Three Hour

13 person Charters

SAVE $1600!!!

CALL NOW TO RESERVE THIS AMAZING DEAL!

ENJOY THE BEAUTY OF LAKE MICHIGAN AND THE CHICAGO SKYLINE ABOARD OUR UNIQUE OPEN SEATING CATAMARAN 'JUST BE'

Our Gemini Freestyle 37 Catamaran is the most flexible and accommodating design available.

Perfect for a day-charter with family and friends, or a memorable meetingmeeting setting with your preferred corporate clients.

Relax and impress on our comfy lounge seating, spacious cushioned foredeck  and aft sling back chair .

Whatever your idea of the perfect outing may be...  Give us a call to reserve your 1st Class cruise today.

Email: [email protected] Call: 1.877.375.0352 or

LOOKING FOR LESSONS, CERTIFICATIONS OR AN AWESOME BLUEWATER SAILING EXPERIENCE? TRY ONE OF OUR  1ST CLASS FRIENDS

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FOR LESSONS and CHARTERS

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Priceless Pampered Private Yachting Experience Charters

Chicago Private Yacht Rentals management and staff would like to introduce you to Adeline’s Sea Moose our well-appointed 68-foot luxury Chris Craft 45-passenger Coast Guard certified Chicago private charter yacht located at J-Dock Burnham Harbor Chicago and her attentive captains and crew that shall provide you and your guests a priceless pampered and private yachting experience.

You won’t be disappointed with our Celebrity Treatment.

Adeline’s Sea Moose continues to be the discreet Just for Fun choice for local and visiting celebrities.

Merriment and cherished memories are fixtures of  Adeline’s Sea Moose charters and by providing Celebrity Treatment on all our charters, we hope you’ll also choose Adeline’s Sea Moose.

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Family Outings, Celebrations and Reunions Yacht Charters

Private Yacht Rental Chicago for Families and Friends

You and your family and friends will be able to share and cherish memories that will be made on our 68-foot luxury Chris Craft yacht, Adeline’s Sea Moose which is exclusively yours to enjoy with an attentive crew to ensure everyone shares a priceless pampered private yachting experience together.

Celebrations Cruises and Special Occasions Yacht Charters

Unique Yacht Rental Chicago for Birthday Celebrations or Any Special Occasion 

Imagine the special memories that will be made on our private Adeline’s Sea Moose yacht that is exclusively yours with a discreet, professional crew attending to all the details, allowing you and your guests to enjoy a unique yacht rental in Chicago for birthday celebrations, or any special occasion, from start to finish.

Corporate Events and Business Functions Yacht Charters

A Yacht Rental Chicago to Impress, Influence, and Inspire.

Offering a priceless, pampered private yachting experience aboard our Adeline’s Sea Moose can be an added advantage to your Corporate Event or Business Function that can Impress, Influence, and Inspire.

Perfect Chicago Private Yacht Rentals Enhanced Matchmaking Experience with lakefront events and attractions

Chicago Private Yacht Rentals Navy Pier Fireworks , Chicago Air and Water Shows , and concerts and events in Millennium Park, Grant Park, and Northerly Island enhanced matchmaking experience with a pampered private Adeline’s Sea Moose yacht charter make for even more priceless moments and memories.

And, being a leisure walk from Alder Planetarium, Shedd Aquarium, and Field Museum, taking a Lake Michigan cruise on Adeline’s Sea Moose is a nice addition to family and friends’ priceless pampered private yachting experiences.

Dinner Parties and Romantic Dining Yacht Charters

A Yacht Rental Chicago for Dinner Parties or Romantic Dining

Romantic dinner for two, an intimate setting for up to twelve guests, or a dinner party for up to 45 guests. we promise and provide a priceless pampered private yacht dining experience aboard Adeline’s Sea Moose.

Chicago Skyline Architecture Tour Yacht Charters

Amazing Yacht Rental Chicago for Docent Skyline Architecture Tour

Chicago is home to some of the most breathtaking buildings in North America. Our Chicago Skyline Architecture Tour charters provide a unique viewing perspective with a docent explaining the history of the City’s magnificent structures.

Non-Profit Events, Fundraising and Networking Yacht Charters

Pampered Yacht Rental Chicago for Charity Events, Fundraising and Networking

Adeline’s Sea Moose provides the perfect private venue and attentive pampering crew to help non-profit organizations strengthen relationships with their present donors and persuade prospective donors.

Marriage Proposal Charters

Bachelorette Bachelor Charters

Wedding Ceremony Charters

Caring and Respectful Ash Scattering on Lake Michigan Farewells

Chicago Private Yacht Yachts staff and Adeline’s Sea Moose captains and crew understand that grieving the loss of a loved one is different for everyone.

You can take comfort in knowing that our ash scattering services on Lake Michigan will be a caring and respectful farewell. Our attended Family & Friends memorials and unattended Captain ceremonies are thoughtful ash scattering on Lake Michigan services honoring and remembering your Loved One.

(224) 601-0220

Charitable charters.

Cruising into a bright future with Inner Voice Chance to win 3.5-hour Lake Michigan cruise for up to 32 people on Adeline’s Sea Moose.

You will not be disappointed

TEXT Only 312-500-7838

Docking Address: J-Dock Burnham Harbor 1559 South Lake Shore Drive Chicago , IL 60605 at the end of Waldron Drive. The first dock north of the Harbormaster’s office.

Office Address: Chicago Private Yacht Rental, Inc 4751 West Touhy Avenue Suite 101 Lincolnwood, IL 60712

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Departure date

Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, 22 boat rentals & yacht charters in chicago, il.

Chicago, IL

boating guide

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
• 22 boat rentals in Chicago, IL
• 22 boat rentals in Near South Side, Chicago, IL
• 22 boat rentals in River North, Chicago, IL
• 22 boat rentals in Streeterville, Chicago, IL
• 22 boat rentals in Near North, Chicago, IL
• 22 boat rentals in Little Italy, Chicago, IL
• 22 boat rentals in West Loop, Chicago, IL
• 22 boat rentals in Near North Side, Chicago, IL
• 22 boat rentals in Gold Coast, Chicago, IL

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
• Cleveland yacht charters
• Michigan boat charters
• Rent a boat in Ohio
• Traverse City boat rentals
• St Clait Shores boat rental

Popular boat types among renters:

• Party boat rental Detroit, Michigan
• Cleveland sailboat rental
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• British Virgin Islands
• La Paz, Mexico
• Cabo San Lucas, Mexico
• Key Largo, FL
• St. Vincent and Grenadines

2-5 Hour Private Boat Charters

Home » Chicago Boat Tours » 2-5 Hour Private Boat Charters

2-5 Hour Private Charter

Chicago boat tours – knock out charters, boat tour description.

Available Options

• Cruise the skyline and enjoy the amazing views along The Chicago River
• Drop anchor after a little bit of cruising and swim. We provide the floats
• Let us hire a “Conversational” Docent and get a private Architecture Tour that isn’t just a lecture
• Drop Anchor in “Connor’s Cove” and listen to a concert at Northerly Island
• Captain is Included in Pricing
• Accommodates 1-6 Passengers
• Great flybridge (upper deck) bench in front of captain’s wheel for 360 view
• Bluetooth stereo to play throughout the boat
• Bathroom on board
• Full coverage interior with couches
• Can still enjoy the view from inside
• Fridge and freezer
• Both boats provide plates, cups, silverware, and napkins
• We have platters/serving bowls to provide if needed
• Bottled water, coolers, and ice is provided

Pricing and Reservations

37' luhrs tournament.

• Per Hour $300 + Tax

Private Charter Photo Gallery

Chicago boat tours, book direct online, architecture tour.

• Cancellations less than 24 hours in advance, deposit will not be refunded.
• Cancellations more than 24 hours, deposit will be refunded.
• In the case of weather-related cancellations by Knock Out Charters, customers will be offered opportunity to re-schedule or be refunded their deposit.

Contact Info

• Phone (312) 613-9799
• Email [email protected]
• Address DuSable Harbor 111 N. Lake Shore Drive Chicago IL, 60601

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