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Boat & Yacht

Rent a Private Yacht in Chicago

If you’re looking to rent a private yacht in Chicago, you have a few options.

Sailo has a selection of bareboat charters available throughout Chicago.

Guests can rent a private yacht for several hours or the entire day, and you can even hire a captain to explore the city’s hidden gems.

Sailo is a great way to find a private charter that is tailor-made to your needs.

Rent a Private Yacht in Chicago – Best Guide


If you’re looking for a luxurious Chicago yacht charter, you’ve come to the right place.

Sailo has a large selection of Chicago charters. Choose from private boat rentals for a few hours to an entire day.

You can even hire a captain who’s licensed to drive the boat.

With an experienced captain at your disposal, you’ll discover some of the city’s best secrets.

Or, choose a bareboat charter to explore the city on your own.

While the windy city may be named so, it is one of the most sublime stops along the Chicago river.

Glistening skyscrapers, amazing art museums, and a foodie’s dream come true make Chicago an excellent stop-off location on a luxury yacht charter.

From deep-dish pizza to playing baseball at Wrigley Field, you’ll have plenty to do during your trip.

With an advanced filtering system, Sailo makes finding the right boat charter in Chicago easy.

You can easily narrow your search by choosing the start date, the number of guests, and the duration of your trip.

You can also filter the results by boat type and price range.

A handy ‘crew’ filter lets you choose if the boat will have a captain or if you’ll be able to hire a skipper.

Chicago Line Cruises

If you are interested in a private yacht charter in Chicago, you can choose one of three options from the company’s fleet: the First Lady, the First Dame, and the MV Amadeus.

The Chicago Line is a well-established, family-owned business that specializes in private boat tours of Chicago.

Founded by former attorneys Paul McCarthy and Terry Johnson in 1981, Chicago Line boasts over ten employees and has been recognized as one of the city’s best tours.

A full-service bar, a professional sound system, and a variety of dining options are just a few of the amenities available to passengers.

The Chicago Elite is the city’s most sophisticated private yacht and features an attentive captain and crew.

Guests can choose between a three or five-hour cruise with custom menus and entertainment.

The crew and captain are highly-rated by previous customers and hold a five-star Yelp rating. Onboard, they offer views of Chicago’s skyline and architectural sightseeing.

One of the best things about this company is its service and the quality of its products.

Sailo’s advanced filters make it easy to find the perfect Chicago boat charter.

By entering your desired start and end dates, the number of guests, and the type of boat you want to rent, you can narrow your search down to the best option for your needs.

You can even filter the results by price range, Chicago boat type, and the ‘crew’ option, which will allow you to determine whether you’ll want a captain or a skipper.

Then, you can choose between a power boat or a sailboat rental, depending on your needs and budget.

Free Spirit Yacht Charters

Whether you are looking for a beautiful luxury yacht, an intimate river cruise, or an exclusive dinner cruise, there is a private yacht charter in Chicago to meet your needs.

Free Spirit Yacht Charters was founded in 1983 by Rich Borrowdale, who sold it to Joe and Angela Donofrio in 2007.

Both were seasoned navigators on Lake Michigan and both had experience with private yacht charters.

Whether you’re celebrating a wedding, an anniversary or any other occasion, Free Spirit Yacht Charters can accommodate you.

The charters can accommodate up to 400 people. There’s ample room for dancing and catering, and you can even enjoy a special evening of dinner and entertainment with your guests aboard.

The crew and captain are highly rated by previous customers. The company offers multiple packages, including a VIP dinner cruise for up to eight guests.

Whether you’re planning a romantic anniversary, bachelorette party or company outing, a private yacht charter in Chicago is the perfect option.

The company’s fleet features two luxury yachts that can accommodate up to 120 people.

You’ll be pampered with onboard amenities and informative tours.

Guests can even celebrate the Fourth of July on the yacht, which is available at select times throughout the year.

Anita Dee Yacht Charters

If you are looking for a beautiful venue for your private yacht charter in Chicago, you may want to consider a company like Anita Dee Yacht Charters.

They specialize in custom weddings and can accommodate groups of up to 400 people.

They can also provide catering and entertainment for your event.

Former customers have raved about the company’s staff and service, and you can expect the same high quality of service.

Anita Difiglio, the owner of Anita Dee Yacht Charters, started her career as an entrepreneur by owning a charter boat, the Summer Mist, in Burnham Harbor.

The Summer Mist was a hit and was capable of accommodating larger groups.

Eventually, Difiglio sold the yacht, but it stayed in the family and was renamed the Anita Dee.

Since then, she has grown her company into Tee Dee Enterprises, Inc.

Originally, the Anita Dee was docked at Navy Pier, but in 1992 the owners moved it to the south side of the Navy Pier, where it has maintained its successful presence for over thirty years.

Today, the charter company averages 180 private yacht charters a year and has entertained over a million guests.

Guests can choose between an eighty-five-foot or forty-foot yacht for a unique experience.

Sophisticated Lady

If you’re in the market for a luxurious private yacht charter in Chicago, the Sophisticated Lady may be the answer.

They offer the largest cruise vessel of its type in the Chicago area, which can comfortably accommodate 49 passengers.

The luxury yacht has a full crew and a comfortable interior, including plush leather seating and a cozy hearth.

Additionally, the Sophisticated Lady is equipped with a full bar and food service.

For those who are looking for a luxury yacht charter in Chicago, the Sophisticated Lady offers the ultimate experience.

Depending on the number of passengers, you can choose from two to 49 guests.

The luxury yacht has a bar and an onsite chef, so you can relax and enjoy the view from your private cabin.

If you’re traveling with a travel mate, you can share a cabin.

Island Party Boat

For a unique experience in Chicago, consider booking a private yacht charter.

The Island Party Boat provides both rental and charter boat services.

They provide an up-close view of fireworks from the river and cruises for groups of two to ninety people. Read reviews from former customers for a true taste of the island life.

You will definitely love this company! The crew is friendly and helpful, and you’ll be amazed by the level of service you receive.

This party boat has everything a bachelor party could want.

The slide, full-size bathrooms, and fun island decor make the Island Party Boat a great choice for a bachelorette party or birthday celebration.

It also comes with a full bar, so guests can have a cocktail or two while enjoying the views of Lake Michigan.

The open bar package was an extra bonus, and there are plenty of other amenities onboard as well.

If you’re planning a bachelorette party for close friends or a birthday celebration, a private yacht charter in Chicago can be the perfect option.

With three private luxury yachts in its fleet, this company has the perfect vessel for any event.

Their captain is licensed by the U.S. Coast Guard and boasts over 40 years of sailing experience.

The boats have outdoor observation decks, and their captain and crew have more than five years of experience.

This company has a five-star Yelp rating, and customers rave about the quality of service and attention to detail.

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