overnight yacht rental chicago

The best luxury yacht rentals Chicago has to offer!

Chicago Private Yacht Rentals management and staff would like to introduce you to the best yacht rentals Chicago has to offer.  Adeline’s Sea Moose is 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 Will Not Be Disappointed

Being the best yacht rental Chicago has…  Adeline’s Sea Moose yacht charters  provide the opportunity to spend  Priceless  quality time together with your family, friends, colleagues, clients, or employees while being  Pampered  by an attentive crew and enjoying the best  Private  yacht rental Chicago has all to yourselves for a memorable  Yachting Experience.

The Priceless Pampered Private Yachting Experiences Chicago Private Yacht Rentals Offers

Family outings, celebrations and reunions 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 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 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.

Dinner Parties and Romantic Dining 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 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 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

Perfect Chicago Private Yacht Rentals pairings with lakefront events, activities 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 pairings with a pampered private Adeline’s Sea Moose yacht charter make for 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 nicely pairs with family and friends priceless pampered private yachting experiences.

Soldier Field Concerts Charter Pairings

Chicago navy pier fireworks 2024, chicago blues festival 2024, millennium park summer film series 2024, chicago air and water show 2024, chicago private yacht rentals for pleasure or business.

We coined the phrase yacht rental Chicago style to help distinguish the yachting experiences we offer from a boat rental Chicago style. Our yacht rental Chicago style provides, for pleasure or business, a 68-foot luxury Chris Craft twin-engine motor yacht, Adeline’s Sea Moose, as opposed to a boat rental Chicago style on a smaller vessel.

Our yacht rental Chicago style and a boat rental Chicago style for intimacy.  Depending on how creative you are,  either a yacht rental Chicago style or a boat rental Chicago style may serve you well. However, for the most intimate of occasions, our yacht rental Chicago style aboard Adeline’s Sea Moose provides the luxury of a private 68-foot yacht and pampering by her crew, where boat rental Chicago style may not.

(224) 601-0220

• A Fountain of Fun for Everyone
• Navigating Luxury: 10 Irresistible Factors That Make Yacht Rental in Chicago a Must
• Hotel conference rooms in Chicago – on a yacht!
• Corporate Team Building Events
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• Boat Rental In Chicago With Captain | Chicago Boat Charters, Captains
• The difference between a nautical mile and a knot
• Hosting High Level Meetings
• McCormick Place Event Hospitality
• Chicago Museum Campus

TEXT Only 312-500-7838

Adeline’s Sea Moose is a well-appointed 68-foot luxury Chris Craft 45-passenger Coast Guard-certified twin-engine yacht located at J-Dock Burnham Harbor Chicago . East of Lake Shore Drive at the end of Waldron Drive. The first dock north of the Harbormaster’s office.

Directions Docking Address J-Dock Burnham Harbor 1559 South Lake Shore Drive Chicago , IL 60605

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

Luxury Yacht Chartering in Chicago

[email protected]

Aspire Yacht Charters

Chicago's premier yacht experience.

Step aboard one of our luxury yachts and marvel at the view. We invite you to explore the spectacular Windy City skyline from the water. You will be captivated by our exclusive yacht and our carefully selected crew members. This is your opportunity to book Chicago’s premier luxury yacht rental service!

Luxury Amenities

Featuring spacious and luxurious lounges and suites with stunning views of Lake Michigan. We offer full service boating services including cleaning and maintenance, gourmet kitchens with high end appliances and entertainment systems.

Professional Crew

We specialize in entertaining clients, meeting with vendors and entertaining potential guests. Our crew will cater to your needs on board and we are happy to accommodate any request you may have!

CUSTOMIZED EXPERIENCES

Curate your yacht experience with catering, bar staff, private chefs and more. Customize your cruise package to make your event one to remember.

Amazing Views

Offering endless sightseeing opportunities! Whether you are looking to enjoy a private sunset cruise on Lake Michigan, hunt for that hard-to-find restaurant or simply relax with friends on your on the dock, Chicago has something to offer every type of guest.

DISCOVER OUR VESSEL

For daily rentals, our luxury models, click the button below to view our vessel in, what people are saying, testimonials, 10 out of 10.

I have chartered many yachts before and I can honestly say that this yacht was one of the best experiences I've had. The crew was very attentive and took great care of us. The yacht itself was very clean and the amenities were wonderful. The food prepared for us was excellent. Overall I give it a 10 out of 10, a must do in Chicago!

Very Professional

I had an amazing experience working with the charter specialists at Aspire Yacht Charter. They streamlined the booking process for us and provided the best options for our private yacht charter in Chicago. I highly recommend!

Top Notch Service!

We had the best time on board. The service was top notch and the itinerary was customized to our needs. Our charter was a hit with all of our guests. They couldn't stop talking it. We will be chartering again next year.

FREQUENTLY ASKED QUESTIONS

What is the capacity of the yacht.

Our maximum passenger capacity is 12 people, excluding the captain and crew. Our passenger capacity is regulated for your safety on board. Capacities cannot be increased under any circumstances.

Are your vessels Coast Guard certified?

All of our boats are Coast Guard-certified. We maintain our fleet regularly to adhere to strict safety regulations and the latest COVID restrictions.

Hours of Operation

Mon - Sun, 9.00am until 9.00pm

Burnham Harbor, 1559 E Waldron Dr, Chicago, IL 60605

[email protected]

Chicago's Premier Yacht Charter Service

Experience Lake Michigan with the ultimate comfort and style through our tailored charter services.

An Elevated Experience

our services

Charters & Rates

Whatever the occasion, do it in style.

Private Charters

• Chicago River
• Lake Michigan
• Corporate events
• and more…

Day Charters

• Milwaukee, WI
• New Buffalo, MI
• Michigan City, IN

Night Charters

• Firework nights
• Casino, Hammond, IN

Sea Ray SLX 400 40ft

Winner of the NMMA Innovation Award, the SLX 400, coined “The Entertainer”, combines peak performance, superior comfort, incredible versatility and style, and state-of-the-art technology

• Wet bar, 2 grills, refrigerator, wine cooler, microwave, 3 TVs
• Fresh water washdown, deck shower
• Platform (launch pad) that lowers into water
• Bathroom with toilet and fresh water sink
• Seating for 15 people
• Sleeps 4 overnight
• Stereo in cabin & cockpit, with bluetooth connectivity
• Satellite radio & weather
• Dual inboard-outboard MerCruiser engines
• and much more...

Streamlined process

How it Works

To confirm your booking, simply agree to the quote, sign the contract, and submit the corresponding deposit.

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highly-skilled professionals

City-Centered, Accessible Luxury

a curated experience

Our Concierge Service

we strive to exceed expectations

Our Happy Clients

What a perfect day out on Lake Michigan! We felt like kings and queens and the boat was as classy as the service. Eleven out of ten experience. 

You won’t find more genuine hosts who want nothing less than the best experience for their guests. Whether it’s a slow cruise down the river or an anchored stay in the Play Pen, you’re sure to be charmed by the magic of the city. They think of everything so you don’t have to, a stress free experience. 10/10 would recommend.

We may be the Second City but Chi City Charters is second to none! Best boat on the lake, period!

We had the best time cruising along the Chicago River on Lock Leader. Our captain and crew were utter professionals and taught us a lot about Lake Michigan and Chicago. Highly recommended to see the city from a different view.

If you have any inquiries, please refer to our list of frequently asked questions (FAQs) provided below. In case you cannot find the answer you seek, please do not hesitate to reach out to us.

A bareboat charter, as defined by the United States Coast Guard (USCG), is an arrangement granting the Charterer (the individual renting the yacht) temporary ownership and use of a vessel for a specified duration. Under this agreement, the Charterer assumes responsibility for the vessel, their guests, hiring their own Crew, and providing their own food and beverages.

It is important to note that the Charterer may either operate the vessel themselves if they possess the required credentials or choose to hire their own Captain and Crew.

However, it is crucial to adhere to the maximum passenger limit of 12 individuals for a bareboat chartered vessel.

For bareboat charters, the maximum capacity is 12 passengers, excluding the Captain and Crew.

The hired Captain and Crew are not counted as passengers. So, to clarify, the Charterer can bring a maximum of 11 guests.

Please keep in mind that infants and children are included in the total capacity count. Your Captain will count as an additional person, and the Crew can range from 1 to 2 people, depending on your specific requirements.

Once your booking is confirmed, Chi City Charters will provide you with a selection of qualified and approved Captains who have extensive knowledge of the yacht.

Our Captains can offer valuable recommendations regarding the number of Crew members you may require, depending on your specific charter plan. They have a network of experienced Crew members who are familiar with the yacht, and they can enhance your charter experience by providing additional safety, assistance, and service throughout your journey.

Alternatively, Charterers are welcome to provide their own certified Captain. It’s important to note that Captains are independent contractors hired directly by the Charterer and are not affiliated with or employed by Chi City Charters.

The rate for Captains typically ranges from $80 to $250 per hour, depending on their skills, experience, and qualifications, and this does not include gratuity.

It is customary to show appreciation to your hired Captain and Crew by leaving a gratuity of 18-25% of the total charter price (excluding the Captain’s hourly rate). Payment and gratuity should be made directly to your hired Captain.

Captains usually accept cash or payment through peer-to-peer platforms such as ApplePay, Venmo, Zelle, and others.

At Chi City Charters, we accept all major credit cards, including ApplePay, Venmo, Zelle, direct deposit, and cash, providing you with flexible payment options.

However, please be aware that we are unable to accept payment on behalf of your hired Captain or Crew, as they are separate contractors hired directly by the Charterer.

We recommend discussing the preferred method of payment with your hired Captain to ensure a smooth transaction process that aligns with their payment preferences.

fun in the sun

Get ready for an unforgettable yacht experience on Lake Michigan! Use our booking app to find your desired date and time, and bring your perfect day in the sun to life.

• Diversey Harbor, 2601 N. Cannon Drive, Chicago, IL 60614
• 319-889-7170
• [email protected]

Send us a message

Please allow 1 business day for follow up.

BOAT RENTAL CHICAGO  

We'll show you the ropes!

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

LUXURY YACHT CHARTERS

A unique chicagoland & lake michigan experience.

Call or Email For Rates & Availability

(312)288-6803

[email protected]

"VINTAGE" 

75' private yacht charter.

TO ENJOY THE SKYLINE OF THE CITY OF CHICAGO FROM A VESSEL ON LAKE MICHIGAN IS BREATHTAKING; DAY OR EVENING

Established in 1986, Luxury Yacht Charters provides a top of the line experience with their family-owned personalization. With a number of yachts available for your pleasure, and more than 45 years experience in yachting, we will take you along the Chicago Skyline, or the Chicago River between high-rise buildings of the city—some of the most beautiful sites to see from Lake Michigan.

From simple and casual to elegant and sophisticated, our seventy-five foot (75’) yacht can accommodate whatever experience you desire. Enjoy a piece of Chicago’s paradise with us—we’ll take care of the rest.

Privately Owned 

Tailor-made excursions  , luxury yacht charters can take your chicagoland boating experience to the next level experience your tailor-made package today, lake michigan - chicago skyline.

Experience the one-of-a-kind Chicago Skyline from Lake Michigan, including the famous  Navy Pier  and popular museum campus of the  Adler Planetarium  and  Shedd Aquarium.

Chicago River

Take romance to a whole new level & experience the majesty of downtown's infamous architecture along the Chicago River. Plan dinner reservations at one of Chicago's top dining establishments on the riverside, or dine yacht-style on board.

FirstMerit Bank Pavilion - Northerly Island

Avoid the crowds and listen at your leisure! Luxury Yacht Charters offers private charters to Northery Island for a live listen to one of your favorite performers.

Rates & Details - p lease contact us for a formal quote on your custom package.

Booking your custom package can be overwhelming - we understand. Our Chicagoland-based staff can help prepare your package with you and your guests in mind. Please contact us to get more information about your custom yacht charter!

PLEASE VIEW OUR PHOTO GALLERY

TAILOR YOUR CHARTER EXPERIENCE WITH LUXURY YACHT CHARTERS TODAY! 

“the whole trip went, without a hitch , you totally hit it just right for us” , “our honeymoon was magical, thanks to luxury yacht charter’s exquisite planning.”, - sara d. -, “thanks luxury yacht charters, we loved every second & would go back there in a heartbeat.”, - laura g. -.

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Basic Information

Yacht Rental Chicago

Yacht rental in chicago.

A yacht rental in Chicago is the perfect way to turn an ordinary day in the Windy City into something extraordinary. 

Why Charter a Yacht in Chicago, Illinois?

Chicago sits right on the shore of Lake Michigan. This makes Chicago the perfect backdrop for a yachting excursion. Cruising near the city gives  spectacular views of the city’s skyline, Millennium Park, and other nearby locations. 

Lake Michigan is also one of the largest lakes in the world. Lake Michigan has 1,640 miles of shoreline and is more than 307 miles long. This  wide expanse of water gives plenty of opportunities for yachting fun. The water is a stunning beautiful serene green-blue. Whether you want to jump in the water, jetski, go for a romantic dinner cruise, or do something else entirely, you can do it from Chicago. 

How to Enjoy Yacht Rental in Chicago with Anchor Rides

Renting a yacht in Chicago and exploring the water around it sounds like a difficult affair. However, it doesn’t have to be. In fact, with Anchor Rides, renting a yacht in Chicago can be incredibly easy. 

Find a Location Near You

First, you’ll need to find a location near you. You can use our website to search for places that will work in Chicago, and you’re sure to find one that suits your situation. 

Select Your Departure Date

Once you have your location determined, you need to pick what date you want to hit the water. You can look through the list of available dates and pick one or more that works for you. 

Choose Your Yacht

Next, you can choose the boat you want to take out. This means browsing through our selection of hundreds of different boats. 

Request and Confirm Availability

With all of this information decided you can submit your request. If everything works out, your request will be accepted. Once it is, you will be able experiences the rental choices you have made. 

Reserve Your Yacht Rental

With all of this confirmed, you can make the actual reservation. This means putting down a small, returnable security deposit, which is what holds your reservation. 

Select Your Crew and Captain

You will need a Captain to pilot your boat for you. Each of our rental boats has a list of Captains who are eligible to work with the boat in question.  You will have your choice of who you want to come out with you. 

Begin Your Outing in Chicago

With all of this complete, you are ready to embark on your excursion. At this point, all you have left to do is show up at the location you determined at the time you determined.  

Why Choose Anchor Rides for Your Chicago Yacht Rental?

Transparent pricing.

With some yacht rentals, it is hard to know what you’ll actually be paying for your yacht rental. You think you’ve got the final price, then the company adds on service fees, cleaning fees, and other seemingly random charges. With Anchor Rides, you don’t have to worry about this; the price on our website is the  price you will pay . 

Convenience

The process for getting a yacht through Anchor Rides is simple and straightforward. You simply have to complete the process on our website and then show up. This avoids the complex process other companies will run you through. 

Customize Your Experience

With Anchor Rides, you  customize every aspect  of the experience. Other companies may limit your choices to a single boat, a single Captain, and a limited number of days. So, if you want an experience tailor-made for you, Anchor Rides is the obvious choice. 

Professional Crew

At Anchor Rides, we make sure to only work with professionals. Everyone coming on the yacht, from  the Captain to the crew, will be well-trained. This allows them to ensure you have a good time while simultaneously ensuring you’re safe. 

Talk to a Charter Expert

The best way to get started with a yacht excursion is by talking with one of our Charter Experts. They know exactly what is possible with a yacht rental and can help you select everything you need. 

Ready to get started planning your yacht rental in Chicago?  Get in touch with one of our Charter Experts and learn more about all of the exciting options available to you!

Yacht Rental in Chicago for Special Events

While you can rent a yacht any day of the week, many choose to rent them for special events. These include: 

Holiday Yacht Charters and Local Events

Make the holidays special for your family or group outing. Here are some ways to enjoy special holidays during the summer season with friends and family:

• Start the summer off with a  Memorial Day boat outing.
• Spend  July 4th on a yacht and watch the Chicago fireworks.
• Plan a special Mother's Day or Father's Day.
• Say goodbye to summer with a  Labor Day boat party.
• Navy Pier Summer Fireworks - From Memorial Day through Labor Day, the Navy Pier puts on a dazzling fireworks display every Wednesday and Saturday night.
• Experience the  Chicago Air and Water Show from a yacht.
• Venetian Night , Chicago's oldest event, dates back to 1958. It includes a boat parade featuring decorated and illuminated vessels followed by a spectacular fireworks display. View this magical event from the comfort of your private yacht.

The Playpen Yacht Party

A popular summer hotspot, the Playpen is an area off Chicago's shoreline known for its calm waters and incredible city views. It's an ideal location for a yacht party with friends and family. Anchor in the Playpen, blast your favorite tunes and enjoy a day of sunbathing, swimming, and relaxing on your private yacht.

Imagine a wedding that ends by cruising into the sunset. With a yacht rental, this is entirely possible. You can end the night and start your honeymoon in the  most luxurious setting imaginable . 

Bachelor and Bachelorette Parties

Many of our yachts have all the amenities you need to host the perfect bachelor or bachelorette party. These yachts accommodate multiple people, have coolers for food and drinks, and have Bluetooth speakers so you can play music. 

Birthday Parties

Want a milestone event to celebrate a milestone birthday? A yacht rental can provide exactly this. You can bring the birthday cake and cut it in the middle of the lake!

Anniversaries

There is nothing more romantic than a date out on the water. With a  yacht rental , you can set out right from Chicago and watch the sunset as you spend a beautiful anniversary together. 

Family Reunions

Family reunions are notoriously awkward. However, they don’t have to be. A luxurious yacht will put everyone at ease and create a better  space to talk and connect . 

Graduation Parties

Graduation should be a genuine celebration. There is no better way to celebrate in style than on an amazing yacht. Celebrating this way will create a memorable experience that will stay in everyone’s mind for life. 

Frequently Asked Questions

How much does it cost to rent a yacht in chicago.

Yacht rentals in Chicago range quite a bit in cost. For a half-day out on the water, you can expect to spend somewhere between $1,000 to $2,000 on average. 

However, that price can be driven up if you want anything more than the basics. A larger boat that can handle more people, a full day of yachting, and any add-ons will cost more. 

All of this is laid out very clearly on our website. If you search for yachts in Chicago on our site, you will immediately get a list of available yachts and the base price they cost. 

How Many Passengers Are Allowed?

The number of passengers will vary depending on the yacht. Larger yachts can typically handle more people, while smaller ones will handle less. 

For yachts in Chicago, the average number of passengers tends to range from seven to 13 maximum guests . However, the best way to find out exactly how many passengers a yacht can take on it is to check the information page about it. Here, the maximum number of passengers will be clearly listed. 

Can We Bring More People Than We Planned?

The answer to this question depends on the situation. However, in general, if the number of guests is still lower than the maximum number of people the boat can handle, it is usually alright to bring them. If it exceeds this number, then it is not permitted. 

What Safety Practices Are In Place?

Numerous safety practices are in place on all of our yacht rides. We follow all relevant laws relating to boat operations to keep you safe. In addition, our Captains are USCG licensed, and the crew is well-trained and will address any potentially dangerous situation in a way that will keep you safe. 

What If the Weather Is Bad?

If the weather is bad on the day of your yacht rental, we can work to reschedule it based on our  cancellation policy . We’ll provide you with a charter voucher for the same amount of the yacht you paid for. You can then use this to schedule another yacht rental within one year.   

Looking to experience the sights of Chicago from the water?  Sign up for your Anchor account and get started today! *Make the link lead to the pop-up for signing up for an account if possible*  

Chicago Yacht & Boat Charter FAQs 

Where do I board my yacht or boat charter in Chicago?

Chicago has 20+ marinas in and around the downtown area. Each of our vessels is docked at different locations throughout downtown. Be sure to check each yacht page for more information.

Where do I find a Captain for my trip?

Anchor only uses USCG licensed captains for all of our boat and yacht rentals. You may select from  our approved list of vetted local captains who are experienced with Chicago’s Great Lakes and waterways. 

When is Chicago’s prime boating season?

Boating weather is typically extremely favorable from early May through most of October. 

Can we bring food and beverages (including alcohol) onboard?

Most certainly you can bring food and beverages, including alcohol for your outing. However, liquids that stain, such as red wine, cranberry juice, etc. are expressly prohibited. Visit our FAQ page for more details or inquire with your concierge. 

Can our concierge provide catering and other services?

Don’t want the hassle of bringing your own food and beverage? Don’t worry. Our concierge can arrange for food and beverage to be supplied from Chicago’s top caterers. Need music or a live DJ? How about an onboard massage? We can handle all of these requests. Just reach out to one of our concierges and they will have all the arrangements made for you.

Be Sure To Read Our Entire FAQ section

To enjoy the best experience, visit our  comprehensive FAQ page where you will find more detailed information on what to expect for your Anchor charter, including weather cancellations, food & beverage allowed on board, and more. 

555-555-5555

[email protected]

CHICAGO SAILBOAT & YACHT RENTALS

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

Whether you are looking for a romantic sailing trip for two, a sailboat for up to 11 people, power boat rental for up to 12 people, or a party boat rental for up to 36, Chicago Sailboat Charters & Rentals has the perfect charter for you, every day of the week!

HOW TO BOOK YOUR BOAT 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 SAILBOAT & YACHT RENTALS 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

Choose Windy City Sailing for your Chicago Sailboat Charter

View All Private Yacht Charters

LUXURY ACCOMODATIONS

Our sailing yachts accommodate 1 to 10 people. We offer charters with captain and crew for groups up to six (6) or a bareboat charter for groups up to ten (10) with a USCG Licensed Captain paid separately. With up-to-date amenities and two bathrooms onboard, we assure the comfort of all our guests.

CUSTOMIZED CHICAGO SAILING CRUISES

All private Chicago sailboat charters depart and return according to your schedule. All Chicago sailboat cruises have three-hour minimums. Charter extensions are available upon request. Yes, we encourage you to bring food and refreshments, including alcoholic beverages.

Our yachts are professionally maintained and equipped.  In addition, we certify, train and employ United States Coast Guard Captains with over 20 years of experience. Because of this, rest assured that you are in excellent hands.  Also, all of our captains are enrolled in USCG mandated drug screening programs.

CONVENIENCE

The yachts are at the North End of Belmont Harbor, just east of Wrigley Field—or 15 minutes from the Chicago Downtown area. Windy City Sailing is easily accessible via Uber, Lyft, taxis, and bicycles. Also, parking is available via the City of Chicago. Gift certificates are available for all Chicago sailboat cruises and bareboat charters. We confirm reservations with a 50% deposit, fully refundable with a seven-day notice. Gratuity is at your discretion (we recommend 20% to our outstanding crew).

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.

Book Your Chicago Sailing Trip Now

WITH WINDY CITY SAILING

We know you will have questions about sailing charters, so feel free to reach out via phone or email.

Please contact Edwina at 773.868.0096 or  [email protected]  for details and pricing.

Frequently Asked Questions

Have you ever wanted to sail but were unsure what it would cost to charter a private yacht? If so, Windy City Sailing is here to help with all your sailing–related questions. We have made things easy to find by categorizing our questions, and if there’s anything you can’t find, feel free to reach out. Our knowledgeable staff is here to answer all your questions about sailing along the wonderful Chicago Lakeside. From planning the perfect corporate outing for out-of-town guests to helping you witness the incredible  4th of July fireworks , we have it all covered!

Review our  FAQ

Preferred Partners

Preferred Partners are the resources we depend on to deliver the highest quality service to our guests. We value them and appreciate their services.

WHAT OUR CUSTOMERS SAY

Leave us a review on Google .    Leave us a review on Trip Advisor .

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42FT Regal Commodore Express Cruiser

Party & Event Boat with upgraded sound system

Set Sail from Downtown Chicago!

New 27' Sea Ray crusier Playpen summertime

33’ Formula Yacht with Large Outdoor Space, Playpen!

20 Passenger Captained Party & Event Boat in Chicago, Illinois!

Cruisers Cantius 41 Foot Yacht. Captain Fee Included!

31ft Luxury Formula 310 Sun Sport

39' Spacious Luxury Updated Yacht for your Special Outing

Fun and pleasure on a spacious and luxurious Yacht!

2020 Sea Ray 40' Lock Leader

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

Enter your desired location and date to explore our fleet of boat, Chicago, IL, United Statess.

Select a captain

Choose to drive yourself or select a USCG licensed captain.

Book with ease

Connect with your boat owner and complete your booking online.

Enjoy your day on the water with friends and family!

Rent a Boat in Chicago

What to know.

The lake is jam packed in the summer season as everyone in the city flocks to Lake Michigan. This is a consequence of the small window of opportunity to enjoy warm days on the water. 

It’s not just on the lake where people gather but along the Chicago River running through the center of the city. Downtown dockage is available but tends to fill up fast so reservations are encouraged. Just like the lake, the boat traffic in the Chicago River gets congested during the season months and does require precautious boating. 

Safety Requirements:

Boating License/Education Rules: Valid Boating Safety Certificate issued by the Department of Natural Resources or an entity or organization recognized and approved by the Department is required.

Life Jacket Requirements: 13 and under must wear a PFD.

For more information, visit the Illinois Department of Natural Resources .

Where to dock your boat, or meet your rental:

DuSable Harbor

Belmont Harbor

Burnham Harbor

Monroe Harbor

East Chicago Marina

Downtown Docks

Weather Conditions

Ask some Chicago locals, and they’ll tell you summers in Chicago can’t be beat. Temperatures in the Windy City start to warm up around mid-May and last through the end of August into the beginning of September—making the summer season ideal for boaters and sailors.

Avg. Temperature High:  Peaks around 82°F in July

Avg. Temperature Low:  Ranging between 54-61°F during fringe months like May and September

Avg. Water Temperatures in Lake Michigan during the Summer: 

40°F in May

52°F in June

67°F in July

70°F in August

66.7°F in September

Chicago Boating Highlights

Between May and September, life in Chicago centers around Lake Michigan. When planning your next Chicago boat rental trip, be sure to add these popular activities and locations to your itinerary.

Things to Do in Chicago by Boat

Cruise the Chicago River in Style

Moorage : Docktown Docks

Wake zone : Yes

Pro Tips : Docking reservations at the Downtown Docks, while transient, are only for 2-hour durations. Plan ahead and submit reservation requests 2 weeks or less before your arrival.

Hours : Varies by location - see each location for details (Pizzeria Portofino/RPM Seafood, Rockwell on the River, City Winery)

Lat/Long : 41.8870° N, 87.6290° W

Google Maps Link

Go Sailing on Lake Michigan

Moorage : Most, if not all, of Chicago’s Harbors can support sailboat dockage.

Wake zone : Yes - in some areas

Pro Tip s: If you’re in search of a Boatsetter Sailing rental, be sure to check out boats listed near Monroe Harbor or 31st Street Harbor.

Seasonality : Sailing season is year-round, but most Chicago sailors stick to a six month period between late spring and early autumn.

Lat/Long : 41.8781° N, 87.6298° W

Party in the Playpen

Moorage : The closest marinas to the Playpen are DuSable Harbor to the south, and Belmont Harbor to the north.

Pro Tips : The Playpen is the go-to destination during Chicago’s annual Boat Scene Party, with over 10,000 attendees and 500-1000 boats tied up. Secure your boat rental early for this event!

Seasonality : Thousands of boat drop anchor in the Playpen each year, with peak season for this location ranging from Memorial Day weekend through Labor Day.

Lat/Long : 41°53'53.2"N 87°36'43.1"W

Where to Go Boating in Chicago

Moorage : Closest dockage is at DuSable Harbor or Monroe Harbor

Pro Tips : Summer Fireworks at Navy Pier are every Wednesday and Saturday from Memorial Day through Labor Day. 

Hours : Opens daily at 10am, but closing times vary by season.

Lat/Long : 41.8919° N, 87.6051° W

Jackson Park

Moorage : Closest dockage is at Jackson Park Inner Harbor

Wake zone : Yes

Pro Tips : There are 192 slips, mooring cans, and star docks, and the harbor can accommodates boats measuring 25’ to 40’ in length.

Hours : May 1-Oct. 31 - Open Wednesday to Sunday from 10am to 6pm; Closed on Mondays and Tuesdays.

Lat/Long : 41.7833° N, 87.5783° W

Lake Michigan Dive Site

Moorage : Depending on which dive site you’re interested in, there are a variety of Chicago marinas to choose to depart from. When at the dive site, you’ll want to anchor or look for local mooring balls.

Pro Tips : Four of the most popular wreck sites include the Wells Burt, the Straits of Mackinac, the Thomas Hume, and the Wings of the Wind.

Hours : While it is possible to dive year-round, Lake Michigan peak recreational dive season falls between May and ends in early November. Visibility varies, but divers can generally expect 35 to 40 feet—or on clear days up to 100 feet.

Lat/Long : Wells Burt (42° 2.748' N, 87° 37.082' W); Straits of Mackinac (45°48′51’ N 84°44′56’ W); Wings of the Wind (41°56.089’ N 87°33.391’ W)

Check Out Additional Chicago Boating Guides

• Boating Lake in Illinois
• 12 Best Chicago Restaurants on the River
• 6 Best Beaches in Chicago
• Lake Michigan Fishing Guide
• Chicago's Green River: St. Patrick's Day History & Boating Guide

Got questions?

Frequently asked questions

How much is it to rent a boat for a day in Chicago?

The cost to rent a boat in Chicago starts at $75 per hour, depending on the amount of time that you would like to use the boat.

How much does it cost to rent a boat on the Chicago River?

The cost to rent a boat on the Chicago River starts at $75 per hour, depending on the amount of time that you would like to use the boat. Rent jet skis, sailboats, yachts, and more along the Chicago River.

Do you need a boat license to rent a boat in Chicago?

Anyone born on or after January 1, 1998 who operates a powered watercraft of 10hp or more needs a Boater Safety Certificate. If your rental is captained you do not need a safety certificate.

How much does a yacht rental cost Chicago?

The cost to rent a yacht in Chicago starts at $275 per hour. The cost varies depending on the boat size and length of the trip.

How much does it cost to rent a boat at a party in Chicago?

Chicago party boat rentals stat at $135 per hour. Party boats can be rented with or without a captain.

Top boat rental reviews in Chicago, IL

CHICAGO FIVE-0H! ...

Private sailing...

I booked the cruise to do my engagement. It was a perfect choice, Nijole and her husband made the trip perfect for...

24 Passenger...

Troy was great with setting up the reservation and answering questions. Very easy communication. The captain and crew...

Set Sail from...

What a special evening we had!! Couldn’t recommend this charter more. Best way to take in the Windy City and with...

We absolutely loved our time out on the lake. Great experience & I would highly recommend

"Beautiful &...

Captain J and Captain Derek made our boating experience truly exceptional. They were professional, responded in a...

Our trip was absolutely amazing! Wonderful hosts! Wonderful communication! Wonderful boat! I will definitely be...

Great trip. Very relaxing. Exactly what we were looking for.

Better than advertised. First time going out in Chicago so a little skeptical and didn’t know what to expect. Captain...

Had an amazing time as a first timer. Captain Ray was our sailor, he’s awesome, great guy, I do recommend getting...

39' Spacious...

New 27' Sea Ray...

Nice boat! William was super helpful and easy to communicate with leading up to the day. Would definitely rent again!

Boat rentals in Chicago, IL

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Chicago's #1 Boat Rental

Book your boat. set sail. make memories..

Knot My Boat Charters is a bareboat rental company that specializes in boat rentals, memberships, and corporate events in Chicago for up to 12 guests. Offering 17 iconic vessels from 33 sport cruisers to 70’ luxurious yachts, our team brings over 20 years of boating and hospitality experience to our clients, 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 your confirmation email for instructions

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.

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Celebrate Labor Day with Yacht Rentals in Chicago

Hiring a Captain for Boat Rentals in Chicago

Book July 4th Boat Rentals in Chicago

“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!!!”  

Payment Methods

Privacy Policy

Terms & Conditions

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

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Corporate Events • Fireworks and Sunset Cruises • Playpen Party in Downtown Chicago • River Trips • Bachelorette or Bachelor Parties • Birthday parties • Hanging out at City Winery or other restaurants on the river • Proposals • Overnight Stays 

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Dor Sea Tours - Chicago Luxury Yacht and Boat Charter

 We provide luxury yet affordable boating experiences. With over 25 years of expertise, we combine our passion for boating with our love for service, providing our customers with unique and customized charter experiences like no other in the Chicagoland area.   Whether cruising the Chicago river,  catching the fireworks at Navy Pier, hanging at the playpen or hosting a corporate event, we take pride in meeting your needs and providing you with a memorable experience on the water. 

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Yachting in Chicago, IL

Whether you want to cruise the Chicago River or go out into Lake Michigan and tie up at the Playpen, the Windy City is one of the most popular American cities for summer day charters. Don’t forget to book early for busy weekends and every Wednesday and Saturday for the Navy Pier fireworks!

38' Meridian

51' Sea Ray

32' Wellcraft Martinique

35' Sea Ray

38' Sea Ray

47' Carver

54' Sea Ray

40' Formula

50' Sea Ray

54' Sea Ray Sundancer

45' Azimut Atlantis

48' Sunseeker Portofino

45' Prestige

60' Sunseeker Predator

60' Sea Ray

40' Sunseeker

55' Prestige

Why charter a yacht in chicago, il, .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.

Time to relax and find your adventure

Our passion for providing our clients with spectacular moments on the water drives us every day

LuxeLife is a boat rental company that offers luxury rentals in downtown Chicago! We are more than just a boat rental company, we are your partner in creating life long memories on the water. Book your boat today and set sail beyond the Chicago skyline.

Booking with us  comes with several unique benefits - the price you pay includes fuel, cleaning, safety training, and access to all of our amenities (including a free lily pad and 2 free inflatable paddleboards!) 

In partnership with BoatSafeChicago, we offer a pre-select group of United States Coastal Guards ("USCG") Captains for you to choose, who are highly trained professionals (licensed, CPR and water rescue certified as well as drug tested regularly)  who will ensure that your boating experience is both safe, incredibly FUN and unforgettable. 

We offer a bareboat charter:

A bareboat charter is where the Charterer (client) has use of a vessel for a period of time 

The Charterer is allowed a max capacity of 12 passengers and you are allowed to bring your own food and drinks

The Charterer will need a licensed captain to operate the boat (LuxeLife Chicago will provide you with a list once you book) .

Captains are paid by you directly and charge $150 per hour (including gratuity)

Your itinerary is completely your choice on the day of the charter! Just tell your captain.

Your itinerary may include the the Chicago River, the “Playpen”, or any location on Lake Michigan within 10 nautical miles from your departure location (docking location). Please note, it can sometimes take 1+ hours to access the river on busy summer days

Our location at the 31st Street Harbor, which is the latest addition to the harbor system in Chicago, provides a unique and exceptional experience for you and your guests. So, why not choose LuxeLife Chicago for your next boating adventure?

Book your luxury boat rental and experience the ultimate in boating luxury today. Booking is easy in just 3 steps

You pick a date & time

We'll send you what to bring & a list of our pre-selected captains to choose from

Bring yourself and your party to the party!

Chicago's exceptional boating weekends or activities not to miss on the lake!

There's a reason why Chicago has been voted "#1 Best Big City in the U.S.” for Historic Seventh Straight Year by Readers of Condé Nast Traveler in 2023. 

We offer rentals everyday of the week and weekends, but below are just a few of the special 2024 summer dates that we know you would love to enjoy on the water!

May 5: Cinco de Mayo

May 25-27 Memorial Day Weekend

June 1: Chicago Yacht Club Boat Show

June 19: Juneteenth

June 22/23: Chicago PRIDE Weekend

June 16 - 24: Sail GP Chicago

July 1/2: NASCAR Chicago Street Race Weekend

July 4 - 7: Independence Day Weekend

July 13: Chicago to Mackinac Race

July 27/28: Milwaukee Air and Water Show

August 2: Chicago Scene Boat Party

August 1 - 4: Lollapalooza

August 10/11: Chicago Air and Water Show

August 24/25: Chicago Triathlon

Aug 31 - September 2: Labor Day Weekend

Fireworks on the lake

Chicago's summertime fireworks displays are one of the most spectacular events in the city. Views from the lake are unparalleled, culminating in an incredible visual and emotional experience with the evening city skyline and fireworks in perfect unison

Celebrate your milestones

Whether you're celebrating a birthday, anniversary, graduation, bachelor/bachelorette party, or any other milestone, LuxeLife offers the perfect setting for a memorable celebration.

Be treated to breathtaking views of Chicago's iconic skyline, while celebrating in style. Our boats come equipped with all the amenities you need to enjoy your celebration in style, including comfortable seating, state of the art bluetooth sound system for playing your favorite music, kitchen, shower and much more

31st St Harbor , Chicago IL, 60616

[email protected]

+1 (312)-779-1329

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Home » North America » USA » 7 EPIC Boat Rentals in Chicago

7 EPIC Boat Rentals in Chicago

The city of Chicago is affectionately known as the ‘Windy City’, though let us tell you that it’s got more going for it than a strong breeze. That breeze though is PERFECT for sailing!

Did you know that Chicago is a great place to hire a boat and get out on the water? Chicago may not be near the sea, but the enormous Lake Michigan is so gorgeous it could rival some of the top tropical destinations in the U.S. And during summertime, Lake Michigan really comes into its own.

Life in the city can be crazy, so renting a boat in Chicago is a sweet way to experience something far different from the ordinary city-break vacation.

You can sail around the ocean-like lake, cruise up and down the Chicago River, or drop your anchor in the Play Pen (Chicago’s wharf dedicated to party boats). For party-lovers, if you drop an anchor here you’ll be sure to have a good time.

Whether you’re travelling with family, friends, as a couple, or with colleagues. Getting out on a boat is, without a doubt, one of the best ways to soak up the atmosphere of the city.

But if you’ve never experienced a boat rental in Chicago before, you might be wondering how does one go about this. Well, dear friends, that’s what this guide is for! Read on to be enlightened.

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Top 3 Yacht Rentals & Boat Charter in Chicago

How to rent a boat in chicago , why rent a boat in chicago, yacht charters in chicago, things to do on a boat in chicago, final thoughts.

36 Foot Sailboat

• > 6 Passengers
• > Captained
• > Budget-friendly 

Luxurious Italian Yacht

• > 12 Passengers
• > Classy Italian Yacht

Two Story Yacht

• > 12 passengers
• > Captained or Bareboat
• > Two story yacht

It’s all well and good to say that you should rent a boat when staying in Chicago , but how does one find a boat?

Introducing, Sailo .

Sailo is an app/website where verified boat owners can list their boats to rent, not just in Chicago, but all over the world. People who are interested in renting a boat can easily browse through the options in their destination of choice, pick their vessel, and send a message to the owner, and boom, you got yourself a boat buddy! It’s like the Airbnb of boats. 

You can apply filters to your search to choose the perfect vessel for your adventure. Each listing provides detailed information about the boat, the extra services on offer and any additional costs they may incur. There are also customer reviews so you can make an informed choice about what to hire, which for anyone looking to hire a boat for the first time will agree that reading other traveller’s feedback relieves a lot of anxiety.

So why should you rent a boat or yacht in Chicago? Why the heck not, we say!

It’s a fun way to celebrate a special occasion, bond with your family, or even tick your first sailing trip off the ol’ bucket list. 

It may not be the Caribbean, but the lakeside beaches of Chicago still boast a tropical vibe and are the place to be during the warmer months. If we compared a picture of people enjoying a boat rental in Miami and Chicago, you would probably have a hard time telling the difference (though admittedly the water temp is a little different).

This is especially epic when you consider Chicago is over 2,500km from an ocean!

When you rent a boat in Chicago, you have the chance to admire the natural beauty and architecture of the city from the water. Even if the weather is cool, it’s still an awesome and unique way to experience Chicago. 

There are options to charter a bareboat in Chicago, which means there’s no captain and you do the sailing yourself. For those with less experience with boats or who want to enjoy their holidays to the max, you can also hire a captain (and sometimes crew) for your trip. 

Once you’ve found your boat, simply check the weather and wind speed and be on your way!

Are you ready to cruise through our top picks? 

We’ve selected the seven best boat rentals in Chicago so you don’t have to. We get that there are a billion different ways to travel, so we chose with different travel styles and budgets in mind. 

So, without further ado, allow us to get stuck into our top picks. 

Best Yacht Rental for Families in Chicago – Two Story Yacht

• Two story yacht
• 12 passengers
• Captained or Bareboat

Fancy a bit of family bonding? Why not rent this two-story, 40-foot yacht and discover the waters around Chicago. There’s a bunch of places that are only accessible by water and the captain of this ship knows all the secrets. 

If you prefer to do it yourself, you can choose to rent this boat bareboat, which means you and the fam are captain and crew. This way you’ll have the freedom to set your own pace and visit the places you want. 

Now you don’t need a boating license to rent a bareboat in Chicago, but you do need some form of boating education certification approved by the National Association of State Boating Law Administrators (NASBLA). And of course, some experience of driving a boat.

On the boat itself, you could use the top floor for reading and tanning and the lower deck for setting the mood with music on the Bluetooth speakers. 

The cabin below has air conditioning if you need a moment to cool off, and there’s even a microwave and a fridge. If you wanna spend the night, it’s got a cabin for up to four people to sleep in. 

Pro tip: bring some extra inflatables with you so you can float in the water off the boat. It will make the chilly water of Lake Michigan a little gentler too. 

Epic Party Yacht Rental in Chicago – Sexy Party Yacht 

• Spacious deck
• 12 Passengers

Remember how we told you about Chicago’s Play Pen? It’s the wharf dedicated to yachts dropping anchor and partying it up. On the weekends, you can find up to 50 boats and yachts living it up here. If you’ve ever watched a music video set on a fancy boat, it’s not so far off from what you should expect. 

Now imagine you rock up to the Play Pen on this sexy 60-foot yacht. Chances are, you and your mates have never looked better. 

The yacht has a massive wraparound sofa inside the yacht’s air-conditioned and window-lined cabin. Of course, it’s nice in there and all, but out on the spacious deck in the open air is the place to be. 

If you prefer to cruise around the Lake while you and your buddies get loose, this is a very good choice for that too. The ship comes captained, and some pretty flashy catering packages are available for you and your crew if you want to leave the food and drinks thing to the professionals. Overnight stays on the yacht can be organized, so your party needs no curfew. 

Over-the-Top Luxurious Yacht Rental in Chicago – Luxurious Italian Yacht

• Classy Italian Yacht

This beauty is a fresh arrival in Chicago after spending her early years enjoying the coastline of Italy. Let’s just say, she transports a whole lotta Italian class to Chicago and Lake Michigan. 

It’s a luxurious choice, but a great fit if you’re organizing a bachelor(ette) party, a special birthday, or a tie-up at the iconic Chicago Play Pen. It’s got a full kitchen, two bathrooms, two cabins for sleeping, and a powerful Bluetooth sound system. This charter comes captained, so all you and your team have to do is rock up and enjoy. 

You’ll feel like a million bucks cruising around on this yacht, and you’ll look it too. This luxury yacht is 66 feet of pure sexiness. Have you seen a picture of that deck? Imagine spending an afternoon lounging in the sunshine on there?  If you rent this yacht in Chicago, you’re going to look hot. It’s basically science. Pop the champagne on ice, darlings!

Wanna know how to pack like a pro? Well for a start you need the right gear….

These are packing cubes for the globetrotters and compression sacks for the  real adventurers – these babies are a traveller’s best kept secret. They organise yo’ packing and minimise volume too so you can pack MORE.

Or, y’know… you can stick to just chucking it all in your backpack…

The Biggest Yacht Charter in Chicago – Giant Luxury Motor Yacht

• Awesome catering
• 749 Passengers

Round up as many as 749 of your nearest and dearest for an intimate soiree on this stunning 111-foot motor yacht. 

We very well realize this giant yacht is out of the price range for most of us mortals, so we’re not going to pretend like this one doesn’t cost an arm and a leg. It’s expensive, but it is the biggest boat for rent in Chicago and a bloody nice one at that. Split between 749 people though and you got yourself a bargain!

This Chicago Yacht charter has three huge decks for everyone to spread out on. Everything is served to the highest quality imaginable – think three-course meals, specialty cocktails, and craft beer. You’ll even get a DJ and a dance floor thrown in to sweeten the deal.

Stuck on ideas for what kind of event you could throw on this bad boy? Allow us to help you out – get married, throw a bloody fancy birthday party, surprise your mum with a private cruise, organise a work team bonding day (don’t you just hate those professional development seminars? Well, not on a boat, you won’t). It’s your event, so get creative, folks! 

It’s an extravagant choice, but if you can, you should. 

The Most Affordable Boat Rental in Chicago – 36 Foot Sailboat

• Budget-friendly
• 6 Passengers

This Catalina 36 foot sailboat is a great budget option for those keen to rent a boat in Chicago. Going for the budget option doesn’t mean you’re skipping out on the vibes with this sailboat. 

The boat features a comfy cabin if you want to chill out of the sun for a while. There is a large deck for sunbathing and taking in the scenery of the Great Lakes. There’s plenty of space for six people to spread out. Of course, if you want to ensure the great vibes, you’ll want a good sound system, and this baby has that too. 

The price of the rental includes a caption, crew service, and a bag of ice to keep the drinks cold. It’s got a sweet set up and it meets the needs of any budget traveler. What more could you want? Get your friends or family together – all aboard, me hearties!

Best Boat Tour in Chicago – Chicago Architecture Cruise

• From $44 per people
• Commentary on the sites
• Up to 15 Guests (per booking)

This river cruise is the way to deep dive into Chicago’s history and culture. Chicago is world-renowned for having unique architecture, and let us tell ya, it’s all the more impressive when viewed from the water.

It’s no coincidence that this waterside city offers cruises down the Chicago River to show off some of its best assets. This tour shows off the best views of the city skyline from the water, including peeks at the famous Navy Pier and Wrigley Building. 

You’ll get live commentary on what’s what in the city while you cruise along all three branches of the Chicago River.

Photography fans, be sure to bring your camera for gorgeous snaps of the city skyline from the river. 

Pro tip: Take the cruise at dusk and enjoy the sunset from the boat. If that time doesn’t work from your schedule, fear not. This tour runs 20 times per day, so there’s no excuse not to squeeze it into your Chicago itinerary . 

Booze Cruise Boat Rental in Chicago – Party Pontoon 

• Cooler and ice provided
• 20 Passengers

All aboard the party pontoon, my friends. It’s common knowledge that a booze cruise is one of the best ways to celebrate with your mates, why not do one in Chicago? You can hire this pontoon and throw a party on either Lake Michigan or the Chicago River. Bring your own booze and food and you can set yourself up for an awesome time on the water. 

This party pontoon comes captained, so you and your buddies won’t need to choose someone to skip the drinks and drive. A huge cooler and bags of ice are supplied, plus, there’s a 1200W Bluetooth sound system for you to connect your favorite tunes. There’s a bathroom onboard for when nature calls, which is particularly important if you’re getting stuck into the beverages (responsibly, of course). 

This is a great boat rental in Chicago if you want to get out on the water and party with your friends in a unique way.

• Admire the city skyline and unique architecture from the Chicago River. River cruises run throughout the day and are a great way to learn more about the city and its gorgeous architecture.
• Drinks on deck. Whether your style is beers on a party pontoon or champagne on a luxurious yacht, get out on the water and have a cold one.
• Explore the Great Lake Michigan. Chicago alone has over 26 miles of scenic lakeside spaces, and some areas can only be explored from the water. 
• Party at the Playpen. Remember how we told you Chicago has a dedicated area for boats to anchor and party it up? Don’t miss this spot for an awesome party.
• Catch some sun. It may not be the tropics, but that doesn’t mean you can’t relax on deck and work on your tan. Be sure to protect your skin with sunscreen and insect repellent to fend off those pesky mozzies. 
• Go on a dinner cruise. Wanna earn some brownie points with your lover? Plan a romantic date night for you and your boo on a dinner cruise in Chicago. You can take in the sparkly skyline of the city at sunset. You can either soak up the gorgeous view or stare lovingly into each others eyes. Sounds bloody nice either way, right?
• Rent a stand-up paddleboard! Stand-up paddleboarding is not only a great workout, but it’s also a lot of fun. Be prepared to take a dip in the icy water. Anyone who has tried before knows you’re basically guaranteed to fall off at some point. 
• Watch the fireworks. Chicago puts on a firework display every Wednesday and Saturday night at Navy Pier, and you can see the show from Fullerton Beach to Navy Pier. Imagine cruising by on a boat and watching the fireworks over the city skyline? 

There we have it, my friends. You came here for the best yacht and boat rentals in Chicago and those are our top picks. 

Whether you’re planning a unique activity on your trip to the city or want to explore the Great Lake Michigan on a sailboat, you should find something here to fit your needs and adventure-level. 

If you can’t find a vessel that floats your boat in our selection, you can browse through other listings on Sailo. Organizing a trip should be fun and easy. We hope planning your trip to Chicago is smooth sailing. 

Happy boating!

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

Aiden Freeborn

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