15 Best & Most-Rated Yacht Rentals in Chicago (2022)

If you’re in Chicago to travel and explore, then we have something exciting lined up for you. Most people dream of ever getting on a yacht, but if you choose to check out the names mentioned on the list today, then you’re going to make that dream come true. If you want to explore Chicago and the uncharted waters quite literally, then we have the perfect article lined up for you. Today we are going to tell you about the 15 best yacht rental services in Chicago, that you won’t be able to pass. This is why we highly recommend reading through the entire list and do choose the one that you find fit. So without further a. Let’s jump right in:- 

Best Yacht Rentals in Chicago (2022)

Chicago sailboat charters

Chicago sailboat charters

The first one on the list is one of the most popular yacht rentals in Chicago. This is b3ecause of the first-class service that they have to offer and hence are quite perfect in terms of renting a yacht. Apart from that, Chicago sailboat charters also rent out powerboats and sailboats. Their powerboat can carry up to 11 people and their sailboat can carry up to 12 people. However, if you have a bigger group, then we would suggest that you get the big boat for rent, as it can carry up to 36 people.

Alcohol can be bought on the big boat, but if you choose to go with the yacht or the powerboat option, then you’d have to bring your own booze. If you’re trying to enjoy a hot day out in the ocean or if you have any dipping fantasies, somewhere away from the shoreline, then Chicago sailboat charters are the ones that we would recommend. They offer great views and time slots, which is why they are a must-visit place when you’re in Chicago.

Wendella tours and cruises

Wendella tours and cruises - yacht rental chicago

The next name on the list is also quite a popular one. They have been in this business for about a century and hence call themselves the original yacht rental company. For people who are looking to admire the architecture of the city from the ocean, wendella tours and cruises are the best options to go for.

Wendella tours and cruises have been rated five stars on yelp by multiple users, which goes to show how credible and great their services are. They have a selection of trips and tours to choose from. This includes the Chicago original architecture tour, the sunset strip, the Chicago river experience, the Chicago fireworks trip, and much more.

They have been in this business for a long time and hence have the experience and skill to give you the best possible tour of the city. This is why we highly recommend checking them out once, before going to any other yacht rental on the list.

Hitech sports fishing charters

Hitech sports fishing charters - yacht rental chicago

Next on the list is a fun activity to list your name on. There are only a few people in the city who have gone fishing with their family members before. But if it is something on your bucket list, then this is the best time to cross it off. If you’re in Chicago and are looking to catch fish and experience the entire process, then Hitech sports fishing charters are here to help.

Hitech sports fishing charters is one of the best sport fishing yacht rental services in Chicago. Since they are a locally owned and operated business, they have more flexibility to offer as compared to the others in the industry. Apart from that, they have more than 3 decades of experience in the industry. If you’re looking to make your day a rememberable one for you and your family, then this is the best thing that we can suggest.

The boatyard

The boatyard

This is one of the best places to rent a boat from. The boatyard has been famous in the city for its exceptionally high-quality yacht and fishing boat rental services. If you’re looking to spend the day in the ocean, then going to the boatyard is probably one of the best places to check out. This is because the boatyard has been in business for a very long time and hence the locals always recommend their yacht rentals as well.

The boatyard is the cheapest yacht rental service in Chicago and hence is the perfect option for people who are looking to explore the coyote on a yacht but don’t have a very big budget. Also. they have kayaks available for those who want to feel the thrill of uncharted waters all by themselves.

North shore marine

North shore marine

If you’re looking to have a gorgeous day out at the Pierre, then this is the perfect option for you. North shore marine is one of the most popular yacht rental services in Chicago because of its high-quality services and specialty tours and travel services. North shore marine is also a great place to be in case you want to experience the first-class cruise on the Chicago River.

They have been in this business for quite a long time and their staff and crew have been praised multiple times. If you’re loo0king to make a memorable day for you and your group, then renting a yacht from north shore marine is a great option. Also, you can buy alcohol on their biggest yacht and also can bring your own booze if you like. This is why we highly recommend checking their services out, before approaching anyone else.

Knockout charters

Knockout charters

Even though the name suggests knockout, they offer only original yacht tours and travels. Knowckou charters are one of the most prominent yacht rentals in Chicago right now. This is because they have a ton of flexibility on offer, which makes them in demand all the time. Their services are usually booked as they cater to smaller groups of 6 or less, making them the perfect activity for a date, parties, or even cruises.

If you have guests coming over and you can’t figure out what to do, then take them out on a nice boat ride at the sunset on knockout charter’s high-quality yachts. Also, you can book their boats for an entire day as well as for a few hours. This makes them perfect for architectural tours and even all-day parties in the ocean. However, the prices may vary according to the package that you select. But overall, their services are great and hence are a must-try.

Chicago party yacht rental

Chicago party yacht rental

As the name suggests, this is one of the most successful party yacht rental services in Chicago as they have been in business for quite a long time. Their experience makes them one of the best places to visit if you’re looking for a yacht rental and hence is a great option to select. Chicago party yacht rental is perfect for birthday parties as their sailor can take you to the perfect spot with great views and perfect ambiance.

You can bring your own booze to the party and make it even more happening. They offer all different sizes of yachts, making them a great option to choose if you wish to take your celebrations to the next level. Just visit their website to book a slot and just get going.

Chicago private yacht rentals

Chicago private - yacht rental chicago

The next name on the list is perfect for any yacht activity that comes to your head. From corporate events to personal life-defining moments, all can be organized at the Chicago private yacht rental services. Their 68-foot luxury yacht is parked at the Burnham harbor Chicago, making them one of the most easily accessible yachts in the Chicago River.

Their private yachts give you a luxury experience of charting uncharted waters. Also, the time slots available vary from 7 am in the morning to late at night for birthday -parties and corporate events. Apart from that, you can also go for marriage proposals there and they will help you arrange everything in terms of decorations. So if you’re looking to make a difference in the type of parties you’ve been to, then hosting one here would definitely stand a chance. Overall, their yacht rental services are high quality and hence are the perfect website to add to the list.

Pinnacle yachts

Pinnacle yachts - yacht rental chicago

Pinnacle yachts as the name suggests is a premium yacht rental service in Chicago. They have been in the area for over 16 years and hence have gathered enough testimonials, that are required to convince you to believe that they truly are one of the best yacht rentals in Chicago.

Apart from their high-quality yachts, which are luxury in general and also have great crew, their prices are not that expensive and hence you can actually think of doing this as leisure without burning a hole through your pocket. Also, pinnacle yachts are located in one of the most accessible parts of the Chicago shoreline, making them a great yacht rental service in general. If you haven’t tried their services yet, then we highly recommend trying them out at least once.

Fun in the sun

Fun in the sun - yacht rental chicago

As the name suggests, if you’re looking to get a free tan session, without having to be bored at the beach, this is the perfect option for you. Fun in the sun, yacht rental service is one of the most familiar yacht rentals in Chicago, which is why they have such positive reviews on their website. People have had their best sailing experience with fun in the sun. they also double up as a party yacht rental, making them versatile and a great option to consider.

Chicago land yacht rental

Chicago land - yacht rental chicago

The next name on this list is also one of the most popular yacht rental services in the region. Chicago land yacht rental has one of the best offers and discounts on watching the shoreline on their premium yachts. They can entertain a group of anywhere between 6-20 people making them really versatile in the ocean. If you have never tried their yacht rentals, we highly recommend taking them out for a spin.

Getaway chartering

Getaway chartering - yacht rental chicago

Last but not least, getaway chartering is also a quite popular place in Chicago to book yachts from as they have been in the business for quite a long time. Getaway chartering is popular for its preset rides and tours, which helps you understand the city much better and appreciate it in aspects more than what meets the eye.

Island party boat

If you’re an “island boy” then you’re in for a treat. The island party boat is a locally owned and operated yacht rental service in Chicago that has made hundreds and thousands of trips in the ocean memorable. Their experience lets them give you the best views as compared to other yacht rental services in Chicago. If you’re ever excited to see the shoreline and watch the sunset with your loved ones, then we highly recommend checking the island party boat out. Also, you can book their yachts for a party and feel like a million dollars.

Chicago yacht rentals

The next name on the list might be a pretty familiar name for the locals. This is because they are one of the best yacht rentals in Chicago, as they have a ton of flexibility to offer. They are a locally owned and operated business making them possess a ton of power in terms of flexibility and the quality of the ride.

They entertain both big and smaller groups, making them one of the most versatile yacht rentals in the city. Their prices vary per season, but usually, they are the cheaper option to go for. If you’re in Chicago for sightseeing, then this is the best rental service that we can recommend.

R & R classic sailing

The next name on the list is yet another very popular yacht rental service in Chicago. R&R sailing is the perfect sailboat rental company as you get to experience one of the best views in the entire city also, their experienced sailors know what time to sail at, to get you the best experience possible. R&R classic sailing has three types of boats on offer.

One is their classic ferry boat trip, which is cheaper but will not give you the best of experiences. However, you can also select their yacht option, which comfortably carries about 10 or more people and is pretty luxurious as well. Also, they have bigger sailboats, in case you have more people to bring along. If you’re looking for a good day out in the ocean while you’re visiting Chicago, then we highly recommend using R&R classic sailing services.


The above-mentioned 15 yacht rental services are the best yacht rental services in Chicago and if you’re looking for affordable and luxury yachts in Chicago, then this list has a variety of those, so scour through to find the one that fits you. Till then, keep scrolling!