With historic architecture and iconic landmarks that don’t disappoint (hello, The Bean in Millennium Park), there’s plenty to see in Chicago—and of course, water plays a huge role in it. But did you know what’s become increasingly in demand as well? Private Chicago yacht charters and yacht rentals. When people want to customize their experience on the water for any range of events—social gatherings, holidays, corporate outings, and other major celebrations—boat charters and boat rentals are your best bet. Not only do they offer a unique venue in breathtaking surroundings, but the amenities provide an unforgettable affair designed with luxury and comfort in mind. The fact that we have a fleet of vessels ranging in capacity and style, which are some of the largest and most lavish in class, just helps seal the deal for hosts seeking the perfect event space.


A yacht on Chicago on Lake Michighan.


What to Expect on Your City Cruises Yacht Charter in Chicago

There’s a lot to look forward to on a City Cruises yacht charter because Chicago features some of the most highly regarded architecture in the states, and the best way to take it all in is (of course) from the water. In fact, we recently shared some of the amazing sites you can expect to see on an excursion. Iconic landmarks and the magnificent skyline make for an unforgettable experience, and City Cruises enhances everything with all-inclusive packages, chef-prepared menus, full bar options, and entertainment that can be customized to whatever you need. Picturesque views are easy to clock and capture, from the climate-controlled interior and the open-air outdoor decks no matter what the occasion—and there are plenty of them that you can plan. From corporate and educational events to social gatherings, weddings, or any type of celebration you’re toasting, a yacht charter helps guests make the most of Chicago.


Why Choose City Cruises for Your Chicago Yacht Charter

chicago cruisesNow that you know Chicago yacht charters are an ideal option for your event, it’s time to get to the good stuff: intel on the City Cruises fleet options. Because once you learn about our offerings it will be easy to determine that we’re the best choice to book. With vessels that cater to guest capacities ranging from 125 to 749 people, and feature stylish surroundings, there’s a lot to consider; but let’s look at two options to get you started. First, there’s the Chicago Elite. It has two fully enclosed, climate-controlled decks, plus an open-air sky deck that provides panoramic views of the city’s spectacular skyline. Dine on the elegant dinner deck, then adjourn to the cocktail deck to kick back, relax, sip on some drinks, and enjoy an elevated view of Chicago’s stunning skyline. For significantly larger groups, the Odyssey Lake Michigan is a four-level dining vessel with three interior climate-controlled dining decks along with a rooftop observation deck. The former includes the elegant topaz deck complete with a dance floor and majestic skyline views; the sapphire deck, which features a bar and dance floor; and the amethyst deck which has a private bar and upper-level skyline views. Onboard, guests will relish the opportunity to indulge in the delicious cuisine, which includes plated-style dining, as well as entertainment and lavish decorative touches throughout the yacht.


Experience Chicago Like Never Before

chicago seadog speedboatSo, there’s experiencing Chicago and then there’s experiencing Chicago. For the former you could be led by guidebooks and roam the streets near iconic landmarks to get an up-close look; but for the latter experiencing these sites as living entities across the city skyline is a whole different story. When you’re cruising on the water, the impact and beauty of seeing these structures front and center is hard to describe—but you know and feel it when you do. The unique perspective you get is leveled up even more when you dictate the pace and are able to choose the specific areas you want to view. Whether it’s the illustrious Willis Tower, Grant Park, Tribune Tower, or the Wrigley Building, Chicago architecture is a feast for the eyes and the ideal way to immerse yourself in the city. Plus, according to Condé Nast Traveler, “Chicago has been voted the Best Big City in the U.S. for a remarkable seventh consecutive year. It’s a momentous achievement and a true testament to the enduring allure of our beautiful and dynamic city.”

You can also add a thrilling boat ride on the Seadog if there are any adrenaline junkies in your group who feel the need for speed.

Unforgettable Chicago Skyline Views 

A boat charter in Chicago offers a front-row seat to one of the most iconic skylines in the world. Cruising along Lake Michigan or the Chicago River, you are treated to spectacular views of towering skyscrapers like the Willis Tower, the John Hancock Center, and the sleek outline of the Aqua Building. The city lights reflecting off the water at night provide a dazzling display, perfect for romantic evenings or festive gatherings. 

Proximity to Architectural Marvels 

From the water, Chicago’s rich architectural history is prominently displayed. A boat charter allows for unique perspectives of architectural feats such as the Wrigley Building, Marina City, and the Merchandise Mart. Commentary from knowledgeable guides can enrich this experience, highlighting the innovations and stories behind these famous structures. 

Vibrant Lakefront and Riverwalk Activities 

Chicago’s lakefront and riverwalk areas buzz with activity, offering more than just a scenic backdrop. These vibrant spaces are lined with bars, restaurants, and parks that host a variety of public events throughout the year, from music festivals to outdoor art exhibits, enhancing the urban boating experience. 




Lake Michigan Yacht Charters 

Expansive Blue Waters and Coastal Adventures 

Lake Michigan yacht charters open up a sea of possibilities for exploration and entertainment. The vast blue waters allow for a range of activities, from leisurely sailing to vigorous water sports like jet skiing and paddleboarding. The experience is not confined to the water; stops at coastal towns such as Evanston, Illinois, or Michigan City, Indiana, offer charming beachside attractions and shopping. 

Perfect for Any Occasion 

The expansive setting of Lake Michigan makes it ideal for hosting events of all sizes, from intimate marriage proposals under the stars to grand corporate events with the city skyline as a backdrop. Customizable options on luxury yachts include gourmet dining, live music, and decor to suit every occasion, ensuring a memorable experience. 


Chicago River Yacht Charters 

A Cruise Through the Heart of the City 

Chicago River yacht charters provide an intimate journey through the core of the city, allowing passengers to see famous buildings and historic bridges up close. This urban adventure is perfect for architecture enthusiasts and photographers looking to capture Chicago from a unique angle. 

Eco-friendly and Educational Tours 

city cruises on the chicago river

In addition to leisure tours, many Chicago River charters offer eco-friendly and educational trips that focus on the river’s ecology and the city’s efforts in urban waterway restoration. These tours provide insights into the sustainable practices and architectural strategies that have shaped the river’s role in Chicago’s urban development. 

Both Lake Michigan and Chicago River yacht charters offer distinct ways to experience the city’s beauty and uniqueness, whether you’re looking for a tranquil escape on the open lake or an educational cruise through the bustling riverway. Each option provides its own set of scenic delights and opportunities for celebration, making Chicago a versatile destination for maritime enthusiasts. 


City Cruise Chicago Testimonials and Reviews

City Cruises prides themselves on service and hospitality. It is their mission to make sure you have a memorable experience onboard their vessels, and top-notch service is a big part of that. Whether you are planning for an insightful sightseeing cruise, a decadent dining cruise, or looking to charter a yacht or boat for an exquisite private event, their experienced staff will help take your plans to the next level in Chicago. Just listen to what their customers have to say!

“We had our wedding reception on the Odyssey Chicago River and they completed exceeded my expectations. The service, food, décor set up, ambiance, and overall execution of our plan was absolutely perfect. We couldn’t have asked for a more unique and fun venue that our guests will never forget.”


Chicago Fleet and Venues


How to Book Your Chicago Yacht Charter with City Cruises

Now that you know what you can look forward to, the question remains: How do you book a yacht charter with City Cruises? The answer: Pretty easily. Just fill out this form and one of our event planners will contact you!


Don’t Be Shy in Chi-Town

Let’s be honest: A city like Chicago is best experienced by boat. Why else would it be surrounded by water making so many of its sights unforgettable when seen from the high seas? So naturally, hosting a group event on a yacht is the perfect way to impress your guests and give them an experience they will never forget. Appropriate for any occasion—professional or personal—comfort, safety, style, and numerous amenities are all provided by City Cruises through our impressive fleet of vessels as well as a booking process that’s super simple. That means there’s no excuse for not choosing to cruise especially if you want to plan a Chicago gathering that you and your guests will remember forever.


city cruises during chicago sunset


FAQs – Chicago Yacht Charters (2024 & 2025)

What types of yacht charters and rentals are available in Chicago?

In Chicago, you can find a wide range of yacht charters and rentals, including luxury yachts for formal events, sailing boats for a leisurely day out, and speedboats for thrilling lake adventures. Options cater to various group sizes and preferences, ensuring there’s a perfect boat for every occasion.

Do I need a boating license to rent a yacht in Chicago?

For most yacht rentals and charters in Chicago, you do not need a boating license as they come with a licensed captain and crew to handle navigation and operation. However, for self-driven boats, requirements can vary, so it’s essential to check with the rental company.

How far in advance should I book a yacht charter in Chicago?

It’s advisable to book your yacht charter well in advance, especially during peak season (summer months) or if you’re planning an event on a specific date. Booking several months ahead can help ensure availability for your preferred vessel and date.

What should I bring on a yacht charter in Chicago?

It’s recommended to bring sunscreen, sunglasses, a hat, comfortable clothing, and a light jacket, as it can get windy on Lake Michigan and the Chicago River. Don’t forget your camera to capture the stunning views and any personal items you may need for the duration of the cruise.

What boats are included in the City Cruises fleet in Chicago?

City Cruises in Chicago boasts an impressive fleet including the Odyssey Lake Michigan, Odyssey Chicago River, Spirit of Chicago, Spirit of Navy Pier, Chicago Elite, and Seadog. Each boat offers a unique cruising experience, from luxurious dining cruises to high-speed sightseeing tours.

Can I book a private event on a City Cruises boat in Chicago?

Yes, City Cruises offers private event bookings across its fleet. Whether you’re planning a wedding, corporate event, or private party, boats like the Odyssey Lake Michigan, Chicago Elite, and others provide elegant settings with customizable packages to meet your needs.

What types of cruises can I experience with City Cruises in Chicago?

City Cruises in Chicago offers a variety of cruise experiences, including gourmet dining cruises, architectural tours, sunset cruises, and special event cruises like fireworks displays. The Seadog also offers thrilling speedboat tours for an adventurous take on sightseeing.

Are meals included in City Cruises in Chicago?

Meals are included on certain City Cruises, such as the dining cruises aboard the Odyssey Lake Michigan and Odyssey Chicago River, where guests can enjoy gourmet meals with the backdrop of Chicago’s skyline. Be sure to check the specifics of your chosen cruise for meal inclusions.

Is there a dress code for City Cruises yacht charters in Chicago?

The dress code for City Cruises in Chicago varies by cruise type. For luxury dining cruises on the Odyssey boats, smart casual attire is typically recommended. For sightseeing cruises like those on the Seadog, casual attire is appropriate. It’s always best to check the specific dress code when booking your cruise.

What unique experiences does Lake Michigan offer for yacht charters in Chicago?

Lake Michigan provides a vast playground for yacht charters in Chicago, offering unique experiences such as swimming in secluded coves, enjoying watersports in the open water, and witnessing spectacular sunsets against the Chicago skyline. The lake’s size and beauty make it ideal for everything from leisurely day sails to exciting water activities and themed parties.

Can yacht charters in Chicago navigate the Chicago River for architectural tours?

Yes, many yacht charters in Chicago offer the opportunity to navigate the Chicago River, providing an up-close view of the city’s renowned architectural marvels. These tours offer a unique perspective of Chicago’s historic and modern buildings, making for an educational and visually stunning experience.

What are some must-see landmarks during a yacht charter in Chicago?

During a yacht charter in Chicago, must-see landmarks include the majestic Navy Pier, the iconic Willis Tower (formerly Sears Tower), the Centennial Wheel, and the Buckingham Fountain. Cruising along the shoreline offers unparalleled views of the city’s architectural wonders and landmarks.

How does a sunset cruise on Lake Michigan enhance the yacht charter experience in Chicago?

A sunset cruise on Lake Michigan is one of the most magical experiences in Chicago, offering breathtaking views of the sun dipping below the city skyline and casting golden hues over the water. It’s a perfect setting for romantic outings, special celebrations, or simply enjoying the serene beauty of the lake at dusk.

What makes a yacht charter on the Chicago River during the evening special?

Yacht charting on the Chicago River during the evening is special because it showcases the city’s vibrant nightlife from a unique vantage point. The reflections of illuminated buildings and bridges on the water create a mesmerizing scene, enhancing special occasions or casual outings with a backdrop of Chicago’s glittering lights.

Are themed yacht charters available in Chicago, and what might they include?

Themed yacht charters are a popular option in Chicago, offering experiences such as jazz cruises, fireworks viewing parties, Halloween parties, and historical tours. These charters often include themed decorations, music, and entertainment, making for a memorable and customized sailing experience.


Original Post Date: August 8, 2023