About this Experience
What you'll do:
Step aboard a private yacht and experience one of the most popular Chicago boat rental experiences on Lake Michigan. Your group will depart from Diversey Harbor and cruise along the Chicago skyline with incredible views of the city from the water.
From there, your experience is yours to shape. Relax at the Chicago Playpen surrounded by boats and summer energy, cruise the Chicago River through downtown, or enjoy open water on Lake Michigan while listening to music with your group. Guests often celebrate bachelorette parties, birthdays, corporate outings, and summer lake days aboard our private Chicago yacht rentals.
Each yacht features comfortable seating, upgraded Bluetooth sound systems, and open deck space for socializing and photos with the skyline in the background. Bring your favorite food and drinks, connect your playlist, and enjoy a private day on the water with friends.
Whether you want a relaxing cruise along Chicago’s lakefront or a lively afternoon at the Playpen, this private Chicago yacht charter delivers one of the best ways to experience summer in the city.
Why we love it for your party:
Chicago's skyline as your backdrop: You're not just on a boat — you're floating in front of one of the most iconic cityscapes in the world. Every photo, every toast, every moment hits different from the water.
Fully private — your crew only: Your music, your drinks, your itinerary — and zero crowds or strangers. The boat is yours from departure to dockside, up to 12 guests, all in your party.
BYOB: Stock the cooler exactly how you want. Champagne, seltzers, whatever the group is feeling. Your boat, your bar.
A fleet curated for celebration: From our 31-foot cruiser to our 51-foot motor yacht, every vessel in our fleet is maintained to the highest standard — so whatever your group size or occasion, you're boarding something worth posting about.
About this experience partner:
Prestige Yacht Rentals operates one of the most popular Chicago boat rental fleets with private yachts from 31 to 51 feet departing from Diversey Harbor on Lake Michigan. We host private group charters for bachelorette parties, birthdays, girls trips, corporate outings, and Chicago fireworks cruises.
Each yacht is professionally maintained and every charter stays fully private for your group. Your crew chooses the music, food, drinks, and how the trip unfolds from departure to return.
Weekday rates start near $150 per hour, which places our Chicago yacht rentals among the most affordable private boat rental options in the city. Licensed captains are available to hire and charters stay BYOB friendly, which gives your group full control of the experience.
If your group plans to celebrate on Lake Michigan with skyline views and time at the Chicago Playpen, Prestige Yacht Rentals delivers the perfect setting on the water.
Additional information:
Capacity: Each charter allows up to 12 guests in line with US Coast Guard regulations. The captain does not count toward the guest limit.
Captain: A licensed captain is required for every charter and is hired separately from our approved captain list. Captains generally charge $100 to $150 per hour. Gratuity is not included. A 20% tip based on the captain’s total rate is recommended.
Food & Drinks: Guests bring their own food and drinks. Yachts include cooler space and storage for your items.
Weather Policy: On the day of your charter, we have the authority to deem whether weather conditions are considered safe or unsafe. Uncharterable weather conditions are typically the result of (but are not limited to) heavy storms, waves forecasted over 4+ feet, small craft advisory warnings, gale storms, and strong winds. Light rain and passing storms are typically considered safe.
In the case that conditions are considered unsafe, our team will work with the guests to temporarily postpone or reschedule your charter to a future date.
Cancellation Policy: Free cancellations until 5 days before the booking start date. 50% refund for cancellations between 2-5 days before the booking start date. Cancellations within 2 days of the booking start date are non-refundable.
What’s included: Fuel and cleaning fees.
Agreements & Waivers: Bareboat charter agreements and waivers must be completed before departure.
Book This Experience
Visit the experience booking site to check availability and book your experience.
LocationChicago, IL
2601 N Cannon Dr, Chicago, IL 60614, USAChicago, IL
Frequently Asked Questions
How many guests are allowed onboard?
To ensure compliance with United States Coast Guard (USCG) regulations and bareboat charter laws, our yachts can accommodate a maximum of 12 passengers. Please note that the Captain and Crew hired by the charterer are not considered passengers under these regulations.
Is a captain included in the rental price?
No, a captain is not included. Per U.S. Coast Guard regulations, our rentals operate as bareboat charters, meaning the charterer (renter) assumes full responsibility for the vessel during the rental period. This includes selecting and hiring a qualified captain from our provided list. The captain must be paid separately, as federal law prohibits us from including a captain in the rental price.
How do I hire a captain?
After confirming your reservation, you will receive an email with a list of approved USCG-licensed captains familiar with our fleet. Guests must directly contact captains to confirm their availability and hourly rates. You may also provide your own captain, provided they hold the necessary credentials. Per bareboat charter requirements, the charterer retains full authority to hire and dismiss the Captain and Crew.
How much do captains charge?
Chicago Licensed captains typically charge between $100-$150 per hour, depending on their experience and availability. Gratuity is not included in their rates but is highly recommended at 15%-20% of the captain's total fee. Payments can be made directly to your captain via cash, Venmo, or Zelle.
What is a Bareboat Charter?
A bareboat charter, as defined by the USCG, is a rental agreement in which the charterer(renter) assumes temporary ownership of the yacht. The charterer is responsible for the vessel, passengers, hiring a captain, and providing any necessary supplies, including food and beverages. The charterer may either operate the vessel themselves(if qualified) or hire a licensed captain.
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What are the available cruising options?
Guests typically choose from three popular options: The Chicago Playpen: Anchor and swim in Chicago's most famous boating spot. Skyline Cruises: Enjoy a relaxing cruise along Lake Michigan, taking in Chicago's breathtaking skyline. Chicago River: Experience the beauty of the Chicago River's iconic architecture.
Are boat tie-ups allowed?
For safety and compliance reasons, we do not permit tie-ups during charters. Connecting multiple boats can unintentionally violate bareboat charter regulations by exceeding the 12 passenger limit, potentially leading to legal and safety issues.
Can we bring our own food and beverages?
Guests are welcome to bring their own food and alcoholic beverages. However, we do not permit red wine, colored juices, or staining foods to prevent damage to the yacht's interior.
Are there coolers or refrigerators on board?
All of our yachts are equipped with either a cooler or refrigerator for guest use.
Can we play our own music?
Our yachts are equipped with built -in Bluetooth speakers, allowing you to play your preferred playlist for an enhanced experience.
Are guests allowed to swim?
Once the yacht is anchored, guests are permitted to swim in designated areas. Each yacht is equipped with a minimum of 14 U.S. Coast Guard - approved life jackets for safety.
Do you provide floating devices?
We offer lily pads as an add - on option for guests who want to relax on the water.
Can we cruise down the Chicago River?
Guests may cruise the Chicago River, but all vessels must pass through the Chicago Locks, which may take up to an hour each way. This can significantly reduce your charter time if you go on a high - traffic day. To ensure a smooth experience, please notify us and your hired captain in advance. Please note, we do not offer Chicago River cruises on Saturdays due to high boat traffic.
Are infants and children allowed on board?
We allow children on board. Please note that they do count toward the total capacity, and children 13 years old or younger must wear a life jacket at all times. We encourage parents to bring infant - sized or appropriately fitted life jackets; if you would like to use ours, please let us know beforehand so we can have them ready.
Where are your yachts docked?
All of our vessels are docked at Diversey Harbor, with both pickup and drop off at the same location. The harbor's address is: 2601 N Cannon Drive, Chicago, IL 60614.
Is parking available at Diversey Harbor?
Street parking is available along Cannon Drive; however, it can be limited on weekends, holidays, and during major events. We highly recommend utilizing rideshare services such as Uber or Lyft to avoid parking challenges. For the most accurate drop-off location, set your destination to "Diversey Harbor" or "2601 N Cannon Drive." A designated rideshare drop-off area is conveniently located near the harbor entrance.
When should guests arrive?
We recommend arriving at least 30 minutes before your scheduled departure to allow ample time for parking, walking to the dock, checking in, and getting settled. On holidays or peak summer weekends, guests should plan to arrive at least 45 minutes in advance to accommodate potential traffic or parking delays.
What is your weather policy?
Safety is our top priority. On the day of your charter, our team will assess weather conditions. Uncharterable weather conditions are typically the result of(but are not limited to) heavy storms, waves forecasted over 4 + feet, small craft advisory warnings, gale storms, and strong winds. Light rain and passing storms are typically considered safe. In the case of unsafe weather, we will work with you to reschedule your charter to a future date.
What is your cancellation policy?
Full Refund: Cancellations made 5 days before the booking date. 50% Refund: Cancellations made 2 - 5 days before the booking date. No Refunds: Cancellations made within 48 hours of the scheduled charter.
