chicago lake michigan yacht rental

WEEKDAY SPECIAL! Monday & Tuesday! For info call, email or text! 708.928.2020

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Our largest most visually stunning and luxurious yacht

Cruise Lake Michigan today, even within the next hour

Cruise aborad the luxurious Espresso yacht today

Rent a yacht and cruise along Lake Michigan.

Take a one of a king cruise along Chicago's Lake front aboard any of our Luxurious Yachts. All of our vessels are one of a kind in their own ways, offering intimate Lake Michigan outings for friends, family, professional associates, conventioneers, bride and groom hosting wedding parties and many more.

Enjoy breath taking views of the Adler planetarium, Buckingham Fountain, McCormick Place, Navy Pier, and many other iconic Chicago Landmarks. Whether seated on the vessels open forward deck or stern deck, or inside on a massive wrap around couch with plenty of windows you're sure to get the best views.

All our vessels are fully certified with the United States Coast Guard and all of our captains have countless hours of experience underneath their licenses. Not to mention our very well-trained crew that will let your worries float away.

Before setting out on your next charter, be sure to choose an itinerary. Will it be:

• A sun filled rendezvous at the Rollicking Chicago Scene.
• A cruise along Chicago skyline with scenic view of the Adler planetarium, Buckingham Fountain, and McCormick Place.
• An evening charter beneath Chicago's dazzling twice—a—week fireworks display at Navy Pier.
• Or rent the yacht and chart your own itinerary (for a modest additional cost).

Act now as summer is fast approaching. Whether a suburbanite hosting a unique neighborhood block party, college students celebrating the arrival of summer, professionals honoring the accomplishments of a colleague, conventioneers in search of a unique outing and a panorama view of Chicago's fabled skyline—or whatever—reserve your Chicago yacht party now before our calendar is filled to the maximum.

For Further Details, Call Us Now at 708-928-2020!

See what others think of us by visiting yelp ! Or visit uf on facebook !

Copyright ©2023 by ChicagoYachtParty. All rights reserved.

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.

Luxury Yacht Chartering in Chicago

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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]

Free Spirit Private Yacht Charters

Experience all-inclusive luxury and set sail across the crystal blue waters of lake michigan., lake michigan, chicago, il, welcome aboard, whether celebrating a birthday or entertaining corporate clients, we personalize every detail of your event to provide an extraordinary experience you’ll never forget. soak in the magic of the chicago skyline. sip on refreshing cocktails and indulge in an array of delicious food. we’re thrilled to have you on board.

• Free Spirit

Our spacious Free Spirit luxury yacht accommodates up to 120 people and is custom-designed for your relaxation and comfort, inside and out. Free Spirit is perfect for larger groups for business meetings, company outings, networking events, family celebrations, weddings or parties. Whatever the occasion, it’s more memorable when it’s a boat!

• Gypsy Spirit

Our Gypsy Spirit luxury charter yacht is perfect for an intimate gathering or a small company outing. The Gypsy accommodates up to 49 passengers, offering multi-level entertaining with a salon, galley, and aft deck lounge area. Sit back, relax and cruise Chicago River or Lake Michigan.

WHAT WE Offer

We make special occasions memorable!

At Free Spirit Yacht Cruise, we go above and beyond to guarantee your occasion is truly special. You can delight out-of-state visitors with breathtaking views of Chicago’s world-famous skyline. Host a casual breakfast cruise with sparkling mimosas.

Need to impress new business clients? Break out of the ordinary and stun clients with an elegant dinner on a cruise along Lake Michigan.

From our attentive staff to the luxurious ambiance, our gorgeous yachts offer the perfect venue for you to host your next event.

Ready to Start Planning Your Event?

Free Spirit Yacht Cruises

708-361-2220

[email protected]

Burnham Harbor, Chicago, IL

Interested in chartering a yacht with us? Contact Free Spirit Cruises at 708-361-2220 or complete our online form. Let’s see how we can help you today!

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The Most Fun You’ll Have With The Sails Up!

The Vagabond | Setting Sail from Montrose Harbor | 601 W. Montrose Dr. – Chicago, IL 60613 | 630-816-1427

Enjoy the awesome Chicago skyline

Take a nice relaxing sunset sail

Chicago Sailing Charters

Group | Private | Corporate Yacht | Event Rentals

At Two Brothers Sailing Adventures Chicago we take great pride in providing a wide selection of sailing charters and adventure options in the Chicago area. Every yacht we charter or sailing package we offer has been designed with safe and fun activities that are also uniquely planned to make the most of your time. If you don’t know about Chicago sailing or yacht rental on Lake Michigan, it is a great getaway in the Spring, Summer and Fall months. Our safety record is impeccable and our charter captains are fully trained and licensed. You are guaranteed to have a sailing adventure with captains and crew that are all accomplished Lake Michigan sailors excited to share their love of adventure sailing and the water, with a passion for entertaining new passengers and friends in Chicago.  It is easy to Charter a sailing adventure by checking our availability . We love seeing our friends return year after year! When you book a Chicago sailing charter or yacht rental adventure with us, you’ll soon see why people love to go ‘sails up’ with us.

We’re Ready to Put Our Sails Up for You

Two Brothers Sailing Adventures is ready to put our sails up for you. It all starts by tailoring the length of your sail within two to three hours, or more. We provide many options and choices including the sites you’ll sail to and see and the fare you’ll be treated to during your trip with us. Each sailing adventure is conducted by one of our licensed captains with the duty of keeping their passengers safe and entertained on beautiful Lake Michigan.

Two Brothers Sailing Adventures is your Chicago sailing destination. We pride ourselves on offering a wide selection of adventure, including small boat rentals, luxury yacht charters and sailing lessons. Whether you’re traveling from the Midwest, or across Lake Michigan, Two Brothers Sailing Adventures is the perfect destination for an adventurous sailing getaway in Chicago. Our licensed charter captains are fully trained, and we guarantee you’ll have a fun, safe sail in the Chicago area. We look forward to welcoming you aboard, and showing you why people love to go “sails up” with Two Brothers Sailing Adventures.

We may be the captain, but when you sail with us, we let you take the helm. Whether you want to sail for two hours or five, see specific sites, or just sit back and enjoy Lake Michigan, we’re committed to providing you with a unique Chicago sailing experience. 

Let’s set sail together and make some great memories!

We encourage you to be yourself unless you want to be a pirate then always be a pirate! We pride ourselves on using ALL of our sails, not just revving an engine and calling it sailing in Chicago. All of our sails fly high barring safety concerns.

Sailing Services in Chicago Include the Following:

Sailing Lessons

Boat Charters

Boat Rentals

Contact us to schedule your next sailing adventure on the Chicago Lakefront. We’re ready to set sail and provide you with adventures of a lifetime for your co-workers, friends and families.

See the beautiful sights – Sail the city front from Museum Row to Navy Pier…

Sail to the historic Chicago Cribs and beyond . You still get the great city views while adventuring a bit further to sea…

Swim Socialize and Sunbathe – Sail over and join the crazy crowds at Chicago’s famous Playpen – a protected anchoring area just off Oak Street Beach where boaters of all kinds park and play…

Sunsets with your sweetheart – This is a couples sail scheduled so that you capture breathtaking views of the sun setting while the city lights are rising – truly a perfect date night…

Sunsets with family and friends – Like the romance sail, you will enjoy the beauty of day turning to night…but on this ride you’ll have to sneak below to get alone because your passengers will be tagging along for the fun…

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LIFE STARTS AT THE PIER

LAKE MICHIGAN

Why mpower charters.

As a frontrunner in the yacht charter industry, we boast an unparalleled wealth of experience and an unmatched track record. While our esteemed position is a source of great pride, our true sense of accomplishment stems from our dedicated team. Each member of our staff is unwaveringly committed to delivering the utmost in service—marked by transparency and reliability. In the realm of yachting, you won't find a more qualified or trustworthy partner than MPower Charters and Yacht Rentals.

YOUR PERFECT

Rent a luxury yacht for as low as $250 per hour

Make your special occasion unforgettable with a Lake Michigan yacht cruise.

Parties, family trips , dinner cruises , birthdays, water sports, weddings…

Make your booking now

Ask us in case of any doubt

ENJOY our Luxury Yacht in Chicago for up to 12 guests!

Our Yacht is perfect for any occasion and features: kitchen, living room, 2 bedrooms, full bathroom with shower, onboard refrigerator and cooler, state of the art sound system which is Bluetooth operated, two kayaks and a sup, huge floating pad (15ft by 6ft), big sundeck with comfortable tanning pillows.

booking process

Complete booking for one of our yachts through our website.

Captains List

After booking, we will send you our pre approved captains list. Hire a captain to operate the yacht for you.

Arriving and Check

We will send you arriving and check in directions to enjoy Chicago from the lake!

Live in luxury on Lake Michigan with our charter yachts

At our yacht charter company, we are dedicated to providing our clients with a luxurious Lake Michigan experience. We have a fleet of high-quality yachts and offer personalized services to ensure that your day on the lake is unforgettable.

With over a decade of experience in yacht chartering, we can ensure that your experience with us will be nothing short of exceptional.

Premium selection

Our two yachts are 100% of the highest quality and are in perfect condition for your enjoyment. With us you are guaranteed the best possible experience on Lake Michigan.

Safety is our main priority. All our yachts are equipped with the necessary safety equipment and our team is highly trained to ensure the safety of our clients.

Competitive prices

We offer competitive prices on our yacht charters without sacrificing quality. The opportunity to experience a luxury yacht for only $199 an hour.

Why should you choose us?

Why choose our yacht charter service?  There are many reasons why we are the best option for those looking to enjoy a high quality yachting trip.

We guarantee the best possible experience on the lake. Both of our yachts are of the highest quality and in perfect condition for your enjoyment. With us, you can be sure that you will have a premium selection of yachts that will exceed your expectations.

Our team of experts have years of yacht charter experience and know exactly what it takes to make your day on the lake an unforgettable experience.

Do you want to know our yachts?

What Our Clients Say

Important information

Please keep the following information in mind when making your reservation.

WHEN AND WHERE?

We charter 3 times per day leaving from Belmont Harbor: 10am - 2pm 2:45pm – 6:45pm 7:30pm – 11:30 pm

Are as low as $199 - $250 per hour on weekdays with a 4 hour minimum per session. Please contact us for weekend and Holiday pricing and don't miss out our MONTHLY SPECIALS OFFER (pricing provided upon request)!!!

Not included in the price, however we will provide you with the pre-approved Captain list to choose from and hire.

Not included in the price and it is $150 for 4-hour session. This fee is collected by the owner upon your booking via QuickPay/Zelle.

We will go boating rain or shine, the only way we will reschedule your reservation is when waves are above 5 feet; In this case you will have an opportunity to reschedule your reservation for another date (based on availability) at no charge.

US Coast Guard regulations

Please note, per US Coast Guard regulations, the Bareboat maximum capacity for rental is 12 passengers plus Captain and we will be able to accommodate only 12 people plus Captain. If you have more than 12 people in your group, we can add another yacht for you.

stay in touch

Do you want to rent one of our yachts? Do you have questions about our services? Contact us today! Fill in the contact form and one of our experts will contact you shortly. We can’t wait to help you plan your next Lake Michigan adventure!

Book today and explore new horizons

“Reserve your yacht today and make your sailing dreams come true! Don’t wait any longer to enjoy the beauty of this spectacular lake aboard one of our high-quality yachts!”

Thanks for visiting our website. We are committed to providing an exceptional online experience. If you have any questions or comments, feel free to contact us.

312-500-3084

[email protected]

Belmont Harbor: 3600 N Recreation Dr, Chicago, IL 60613

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Interested in NIGHT FIREWORK CRUISE?

We have it covered, night cruises available wednesday’s and saturday’s.

    Wednesday and Saturday   Night Fireworks Cruise                                                                          SPECIAL                                                                          7:30pm-11:30pm – $1,000 plus Gas and Captain fee.

*Holidays and Special Weekends are excluded.

Welcome aboard Chicago's largest chartering catamaran "Latitude Adjustment". With a spacious cockpit design and roomy interior, she's the perfect choice for any occasion. 

A 38' Lagoon Catamaran

Enjoy a Private Cruise!

Learn to Sail a Catamaran

You're the Captain

Chicago Boat Rental

The best view in the city.

Come experience the calm side of Chicago. Nautical Chicago Boat Rentals allows you to explore on your own terms. You are the Captain. Cruise, Fish, or Swim. Lake Michigan is yours. Our boats are carefully chosen to be easy to drive while still being a capable big water boat. Book your Chicago boat rental today and experience what the city has to offer on the Great Lake Michigan!

Lake Michigan Boat Rental

Looking for the best option to explore the lake on your own? We offer Lake Michigan boat rentals for you to start your adventure today! Explore Lake Michigan like never before – be your own captain, lead your own crew.

Chicago Boat Rentals

Nautical Chicago Boat Rentals has boats waiting for your adventure out onto Lake Michigan. Forget about the hassle of owning and maintaining a boat, rent one of ours! Trust only us when it comes to booking your Chicago Boat Rental.

Testimonials

Best Chicago Boat Tours

Knock out charters.

2-5 Hour Private Charters

Take a cruise tailored to your preferences. Spend some time anchored, sunning or swimming! Let us customize the perfect cruise for you. I don’t think we have ever said no unless it was illegal.

Built to cruise the ocean, she plays on Lake Michigan with ease. With plenty of space, this boat has all the amenities and comforts of home. This boat is the pride of the Chicago Charter Boat fleet.

Special Chicago Boat Trips

Marriage Proposals

You waited your whole life to meet this person and to ask what probably will be the most important question you ask in your entire life. They waited their whole life for you to ask this question.

Casino Package

We depart Chicago and head South to The Horseshoe Casino in Hammond. We drop you off right at the parking deck for some casino fun. We can either wait for you or help you arrange a Limo back to the city.

Architecture Tour

We depart Chicago and head South to The Horseshoe Casino in Hammond. We drop you off right at the parking deck. We can either wait for you or help you arrange a Limo back to the city.

Contact Us or Book Direct Online to Make a Reservation

Knock Out Charters is an award-winning company in Chicago. We want you to be as happy as we are to be enjoying Lake Michigan and the spectacular views of Chicago from both the Lake and The Chicago River...

The Captain

Licensed Master Captain Chris Connor has been boating for over 40 years on a myriad of both Power and Sail boats. He has been on Lake Michigan for over 20 years, and the passion has not waned one bit...

Chicago Boat Trip Photo Gallery

Contact info.

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

Book Direct

• 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.

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Boat & Catamaran charter in Chicago - Yacht Rental

Chicago yacht rental.

The shimmering waters of Lake Michigan are a sight to behold, and what better vantage point than from the deck of a luxurious yacht? As the Windy City’s skyline rises majestically in the background, Yachting.Rent invites you to immerse yourself in an unparalleled sailing experience in Chicago, Illinois. Our mission is to transform your yachting dreams into a reality, backed by our commitment to excellence and unparalleled customer service.

Chicago boasts a rich maritime heritage, and Lake Michigan’s expansive waters have been a sailor’s paradise for generations. Whether you’re planning a romantic evening cruise to catch the city’s enchanting sunset, a family day out exploring the lake’s hidden gems, or a corporate event that leaves an indelible impression, Yachting.Rent offers a fleet tailored to your desires. From sleek, agile vessels perfect for a quick tour to larger, opulent yachts equipped with every modern amenity, our range guarantees the ideal fit for your Lake Michigan adventure. Our seasoned team prioritizes your safety and satisfaction, ensuring that each journey is as seamless as it is memorable.

Yet, it’s not just the yacht that makes the journey; it’s the backdrop. Chicago’s vibrant waterfront, punctuated with landmarks like Navy Pier and the picturesque beaches of the North Shore, offers endless entertainment. As you sail, you’re treated to a dynamic fusion of urban grandeur and natural beauty. The city’s iconic skyscrapers, such as Willis Tower and John Hancock Center, cast their reflections on Lake Michigan’s azure waters, creating a spectacle that remains etched in the memory. Partnering with Yachting.Rent means you’re not just renting a yacht; you’re embarking on an experience, a voyage that captures the essence of Chicago and the majesty of Lake Michigan.

Daniel Goldman

CEO of Yachting.Rent

Boat & Catamaran charter in Chicago

Bali 4.5 – 4 + 2 cab. – Adria Chicha – 2017

Lagoon 450 F – 4 + 2 cab. – Shiva – 2018

Lagoon 42 – 4 + 2 cab. – Hanselli – 2024

Lagoon 42 – 4 + 1 cab. – pirelli – 2024.

Saxdor 320 GTC – Olivia – 2022

Saxdor 320 gto – kali – 2022.

Why Choose Us

Yacht charter in Chicago

Nestled against the bustling metropolis of Chicago, the vast expanse of Lake Michigan awaits exploration. Yachting.Rent proudly presents its premier yacht charter services, marrying the thrill of sailing with the luxury and comfort of our world-class fleet. Our dedication lies in curating the perfect maritime experience for you, set against the mesmerizing backdrop of Chicago’s iconic skyline and the serene waters of Lake Michigan.

Lake Michigan, with its clear blue waters and gentle waves, is a sailor’s dream, and Chicago, with its rich history and vibrant waterfront, provides an unparalleled starting point for your yachting journey. Whether you envision a day of relaxation, cruising along the lake and basking in the sun, or an action-packed adventure navigating the broader stretches of Lake Michigan, Yachting.Rent is poised to make your vision come to life. Our range of vessels is diverse, accommodating both intimate gatherings and larger parties. Each yacht in our fleet is maintained to the highest standard, ensuring safety, comfort, and a touch of opulence. Moreover, our experienced crew is trained to cater to your every need, guaranteeing a seamless sailing experience.

As you charter across Lake Michigan with Yachting.Rent, the city of Chicago unfolds before you in a panorama of architectural marvels and natural beauty. From the historic charm of Navy Pier to the towering presence of skyscrapers like the Willis Tower, your journey will be punctuated by unforgettable sights. To augment your experience, our charter packages can be tailored with a variety of amenities, be it gourmet dining, guided tours, or water sports. Entrust your yachting aspirations to Yachting.Rent, and we promise to set the sails for an extraordinary Lake Michigan adventure.

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About Chicago

Why is Chicago a good sailing destination?

Chicago, famously known as the “Windy City,” is more than just a moniker; it’s an invitation to the adventurous souls yearning for a unique sailing experience on the expansive waters of Lake Michigan. Lake Michigan’s vast azure waters, juxtaposed against Chicago’s magnificent skyline, present a rare blend of urban excitement and natural tranquility, creating a sailor’s haven in the heart of the Midwest.

With Yachting.Rent, embark on a journey across Lake Michigan, which boasts its own sea-like characteristics without the typical challenges of ocean sailing. Its freshwater allure is different from the briny deep seas; its waves are inviting, and its breezes, especially during the summer months, are consistent and favorable for sailing. While the lake provides a spacious playground for avid sailors, Chicago’s coastline offers a multitude of anchorages and marinas, perfect for those brief pauses or nighttime halts. As the sun sets, the cityscape comes alive, painting a silhouette of skyscrapers with the orange and purple hues of the setting sun – a sight that remains etched in the memories of many sailors.

However, what truly elevates Chicago on Lake Michigan as a prime sailing destination is the blend of experiences it offers. With Yachting.Rent, not only can one navigate the waters but also immerse in the city’s rich cultural tapestry. After a day of sailing, dock at the famous Navy Pier, indulge in Chicago’s renowned culinary scene, or dive into the city’s vibrant arts and music festivals. With world-class museums, theaters, and architectural wonders just steps away from the shoreline, the city ensures that the adventure doesn’t stop once you’re back on land. In essence, Chicago, with its dynamic blend of water and urban life, promises a sailing destination unlike any other.

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What Choose

Sailing boat or Catamaran, what to sail in Chicago

The majestic Lake Michigan, with its expansive waters bordered by Chicago’s iconic skyline, offers a spectacular canvas for sailing enthusiasts. But a critical decision awaits every sailor: should you choose a traditional sailing boat or venture with a catamaran? Yachting.Rent is here to help you navigate this decision, ensuring your Lake Michigan journey is as memorable as the Windy City itself.

Sailing boats, with their deep hulls and keels, have been the quintessential choice for many due to their rich maritime legacy. Their design offers stability, especially in the varying wind conditions prevalent in Lake Michigan. For those who enjoy a responsive and tactile sailing experience, where every gust and wave is felt, a sailing boat is your ticket to an intimate communion with the lake. They’re also typically easier to maneuver into Chicago’s many marinas and docking spaces, given their singular hull structure. Plus, there’s something undeniably romantic about hoisting the mainsail against the backdrop of a setting sun, with the Chicago skyline silhouetted in the distance.

On the flip side, catamarans, with their dual hulls, have been gaining popularity among the modern sailors of Lake Michigan. Their design translates to increased stability and spaciousness, making them ideal for larger groups or those planning extended stays on the water. The wider deck offers ample space for relaxation, sunbathing, or even a lakeside barbecue. Catamarans also have a shallower draft, allowing them to explore areas that deeper-hulled sailing boats might avoid. While they might require a slightly different skill set to maneuver, especially in tighter marinas, their speed and stability in diverse conditions make them a formidable choice for those looking for a blend of adventure and comfort on Lake Michigan.

In conclusion, with Yachting.Rent, whether you lean towards the classic charm of a sailing boat or the modern allure of a catamaran, your Lake Michigan expedition is guaranteed to be an unforgettable experience. Both vessels have their unique strengths, and your choice hinges on your sailing preferences and the kind of memories you wish to craft on Chicago’s cherished waters.

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Yachtapalooza, 1-day Chicago boat show on Far South Side, 'perfect for aspiring sailors'

CHICAGO (WLS) -- It might be a chilly spring day, but hundreds are getting ready to set sail at the 25th Yachtapalooza at Crowley's Yacht Yard on Chicago's Far South side.

Grant Crowley is the owner of Crowley's Yacht Yard.

"This is a get spring going for us," he said of the yearly one-day boat show.

Crowley is knotting together different sailing organizations from all walks of life stretching Chicago's nautical community.

From hands-on seminars and demonstrations, highlighting the vital how-tos of sailing, to budget-friendly boats on sale, organizers say Yachtapalooza is perfect for aspiring future sailors.

"We have 12 seminars going on. We even have sail makers here teaching how to trim your sails," said Crowley.

Yachtapalooza also supports nonprofit organizations like No Salt Sailing that helps veterans heal from unseen wounds through sailing.

"Once you get out there and the sails are up, you turn off the motor, there's nothing like it in the world for tranquility," said No Salt Sailing founder William Shehan. "I've done meditation, I've done martial arts, I've done all those things and it is an act of meditation."

Mt. Carmel High School is also showcasing its newly-formed sailing program. They want to recruit young sailors eager to get on board.

"Just to see them accomplish things, watch them become more confident in what they do. Appreciating the value of teamwork, learning new skills, just the whole ball of wax," said Bob Szyman, Mt. Carmel Sailing.

The weather might be brisk now...but these sailors have their compasses set on a warmer horizon.

"There's nothing more sublime than being two miles out on Lake Michigan in a sailboat, beautiful day, sun's out and we've got our gorgeous skyline in the background. You can't beat it," said Szyman.

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