If you want to experience Chicago like a boss, then it’s time to ditch the typical tourist traps and try something different. And what could be better than cruising around Lake Michigan, sipping on cocktails, and enjoying the breathtaking skyline of the Windy City? That’s right! It’s time to rent a yacht! 

Chicago yacht rentals have been gaining popularity over the years for various occasions – from weddings to corporate events or just a private affair with friends or family. The beauty of the Chicago Yacht industry is that multiple rental options are available, catering to different budgets and group sizes.

Let’s dive deeper into all you need to know about Chicago yacht rentals – from where to rent them, what types of yachts are available, and how much they will cost.

Where can you Rent Yachts in Chicago?

You can book your dream boat trip across Lake Michigan in many places. One popular spot is Navy Pier – located in downtown Chicago. Here you can easily find many vendors offering an array of luxurious boats along with top-notch amenities such as onboard bars and meals prepared by professional chefs on deck.

However, it’s worth looking into if you want more personalized services or crave greater tranquility out on the water away from other tourist spots like Shoreline Sightseeing Tours. 

Watch this video to get a glimpse of Navy Pier:


Types of Yachts

When it comes down to boat types for your rental experience – their availability varies based on packages offered by each vendor– But some common examples include:

  1. Sailing Boats: These gorgeous yachts use wind energy instead of engine power. Typically these boats come equipped with multiple sleeping quarters below deck so guests can escape from sunburn while still basking up above water when they’re ready for action again.
  2. Power Boats: Fantastic for those who want more control over speed and direction. These offer a smooth ride compared to sailboats since motorized boats don’t rock as much in the wind.
  3. Luxury Yachts: They come with plush amenities like hot tubs, steam rooms, and sound systems that can be controlled from anywhere on board or ashore using your smartphone through a mobile app, most often provided by the rental company. 

My Personal Experience: My Sailing Journey on Lake Michigan

Gather ’round as I regale you with the tale of my nautical escapade on the shimmering waters of Lake Michigan. Picture this: a sunny day, a cool breeze caressing your cheeks, and the alluring call of the open sea. Yes, dear travelers, I’m talking about my unforgettable experience of renting a yacht in Chicago and setting sail on the aquatic playground that is Lake Michigan.

The journey began with a sprinkle of excitement and a dash of curiosity. As we boarded the elegant yacht, aptly named “Aquatic Dreamer,” I couldn’t help but feel like a true captain of the seas. The crew greeted us with warm smiles and assured us that our voyage would be nothing short of extraordinary.

Once we cast off from the bustling harbor, the urban landscape of Chicago slowly faded into the horizon. The city’s iconic skyline bid us farewell as we ventured into the untamed waters. I couldn’t help but marvel at the juxtaposition of the concrete jungle against the vastness of the lake—a sight both awe-inspiring and humbling.

Watch this video to get a glimpse of how it looks to sail on Lake Michigan:


As we glided across the lake’s glistening surface, our expert captain skillfully navigated through the waves, imparting a sense of security and tranquility. The yacht’s pristine white sails billowed in the wind, and I couldn’t resist the urge to exclaim, “Full steam ahead!” Though, admittedly, “full sail ahead” would have been more nautically accurate.

1st Destination: Navy Pier

Our first destination was the renowned Navy Pier, a bustling hub of entertainment and merriment. The panoramic view from the yacht offered a fresh perspective of this beloved Chicago landmark. From the Ferris wheel’s majestic spins to the laughter of families enjoying the attractions, the vibrant energy of Navy Pier was truly infectious.

But our adventure had just begun! As we cruised farther along, the cityscape gave way to unspoiled natural beauty. Lake Michigan stretched as far as the eye could see, its cerulean expanse mirroring the vastness of the sky above. The sailboat gently swayed with the rhythm of the waves, and I found myself mesmerized by the tranquil waters, losing all track of time.

Eating Seafood onboard

The voyage was not only a feast for the eyes but also a treat for the taste buds. The yacht’s onboard chef surprised us with a delectable spread of gourmet delights. From succulent seafood dishes to artisanal cheeses and fine wines, it was a culinary experience fit for royalty. We indulged in the scrumptious feast, savoring every bite while the sun dipped below the horizon, painting the sky in a vibrant tapestry of colors.

As the day gave way to the enchanting twilight hours, the city lights of Chicago illuminated the skyline like a sea of stars. The once-bustling metropolis now looked like a magical realm, and I couldn’t help but feel like a character in a fairy tale.

But what is a sailing adventure without a dash of thrill? The yacht crew, sensing our adventurous spirits, offered us the opportunity to take the helm and steer the vessel. With a combination of trepidation and excitement, I gripped the wheel and felt the power of the wind in my hands. It was a moment of sheer exhilaration—a taste of the freedom that comes with sailing the open seas.

As the night sky enveloped us, we made our way back to the harbor, guided by the gentle glow of the lighthouse. Our unforgettable journey had come to an end, but the memories of our nautical escapade would forever be etched in our hearts.

Renting a yacht in Chicago and sailing on Lake Michigan was more than just an adventure—it was a soul-stirring experience that left us with a profound appreciation for the beauty of nature and the magic of the high seas. So, my dear adventurers, if you ever find yourself in the Windy City, be sure to seize the opportunity to set sail on the waters of Lake Michigan. It’s an adventure that will ignite your sense of wonder and leave you with a lifetime of cherished memories. 

How Much Can You Expect to Spend on Chicago Yacht Rentals?

Now let’s talk about the big question that everyone has – How much will it cost? The answer is simple: It depends!

The cost of renting a yacht varies based on factors such as group size, type of boat rented, duration of the rental period, and included services throughout your trip. Generally speaking, though, if you’re searching for a budget-friendly option under $1000 per day, then it is realistic to expect a sailing yacht between 30-42 ft range as these tend to be cheaper than larger luxury yachts which can easily go above several thousand dollars per day depending on demand (e.g., during peak summer months).

So whether you’re looking for an affordable option or want exclusivity with high-end luxuries available onboard – there’s something just right for every taste level here in Windy City!

Safety Measures while Renting

As with any water transportation activity, guests should brush up on their basic swimming skills before leaving the shore. Other important safety tips include always wearing personal flotation devices, especially for children under 12 years of age. Vendors will also provide life jackets and training material and recommend online videos as supplementary practice areas.


All in all, renting out a yacht at Chicago’s Lakefront ensures that you get an experience unlike any other. It doesn’t matter if you’re a first-time visitor or have been living here all your life – there’s something special about traversing downtown in style while sipping on cocktails with the sound of waves underfoot. So whether you want to impress clients, gather some friends for a long weekend getaway, or have the family adventure of a lifetime, book a yacht rental today and enjoy Chicago like never before!

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“The Jaded Traveler”. Ron Rossi was born and raised in New York. A globalist at heart, Ron is a marketing director by trade, and has lived and worked around the world including Asia, Europe, Africa, and South America. Food is one of the best ways to learn about a country, a people and a culture. So, Ron is always looking for the best in mid-range to budget and street food. He is always on the hunt for a good meal anyone can afford. It is the food of the average citizen that excites him. And with having visited close to 100 countries on 6 continents so far, there have been some pretty good meals.