Sunset Cruise
Sail into the evening as the city lights begin to sparkle. Feel the breeze, sip champagne, and watch the Chicago skyline transform under a golden sky. Perfect for couples, friends, or anyone seeking a serene escape.
Private Party
Your own floating venue — music, cocktails, and the open water as your stage. From birthdays to reunions, our luxury yachts set the scene for nights you’ll never forget.
Corporate Events
Impress clients or reward your team with a unique on-water experience. Blend business and pleasure as you network, dine, and take in the skyline aboard a world-class vessel.
Fireworks
Watch Chicago’s summer fireworks from the heart of the Playpen aboard your private yacht. Enjoy stunning skyline views, music, and drinks as bursts of color light up the night over Lake Michigan. Perfect for celebrations or unforgettable evenings on the water, this experience captures Chicago’s energy like nothing else.
Special Occasions (optional)
Celebrate life’s biggest moments in unmatched style. From proposals to anniversaries, we create experiences that are as extraordinary as the milestones themselves.
Have a Questions?
Everything you need to know for your perfect day on the water.
Per the USCG, a bareboat charter is a demise charter where the Charterer (renter) takes temporary ownership of a vessel during the chartered time. As the temporary owner, the Charterer is responsible for the vessel, his/her Passengers, selecting a capable Operator/Captain, and furnishing supplies such as food and drinks. A bareboat chartered vessel may not exceed 1 Charterer (the renter) + 12 Passengers (13 total) before a hired crew, regardless of whether it is moored, underway, or anchored.
Yes, a 30% deposit is required to confirm your booking, with the remaining balance due 7 days before your charter.
We recommend booking at least 2–4 weeks in advance, especially for peak summer weekends, as availability is limited and popular dates tend to fill up quickly.
We accept all major credit cards, bank transfers, and secure online payments.
Yes, bareboat (13 passenger) charters can travel on the Chicago River. Please note that the Chicago Locks can take up to an hour each way during busy times, which can significantly reduce your boating time if you go on a high-traffic day. If you plan to visit the Chicago River, please let both Chicago Luxury Yachts and the Operator/Captain know in advance
Absolutely. Our charters are tailored to your preferences, whether you want a skyline cruise, a swim stop, or a sunset sail.
Food and drinks are not included, but you’re welcome to bring your own beverages and catering. All our charters are fully BYOB and BYOF, allowing you to enjoy your favorite selections on board.
Absolutely! You’re welcome to bring your own decorations and entertainment. Our upgraded sound systems connect easily via Bluetooth, so you can play your favorite music. We just ask that all décor items are boat- and water-friendly.
Our yachts are located at two premier harbors in Chicago. Chiscapes is docked at Burnham Harbor, while Limitless and Stayin A Float are located at 31st Street Harbor. Your concierge will provide exact docking details, parking information, and arrival instructions before your charter.
31st Street Harbor offers limited parking, and we strongly recommend ride sharing or car services. Some nearby lots or street parking may be available, but can fill quickly in summer months. Burnham Harbor (Chiscapes) also has multiple parking lots and street parking options; however, availability depends on museum traffic, concerts at Northerly Island, and events at Soldier Field. Plan ahead or opt for ride sharing to avoid delays.
Yes, guests are welcome to provide their own food and beverages, including alcohol. Onboard we provide a complimentary cooler, refrigerator, and a well-equipped kitchen for you to use. We suggest avoiding glass containers and staining liquids (like red wine, cranberry juice, etc.) as they can damage the upholstery and may result in a cleaning or damage fee. For safety and fire prevention reasons, each vessel's stove is disconnected, and cooking inside the cabin is not allowed. Microwave use is available while docked and plugged into shore power, but is not guaranteed while underway.
Yes. All of our captains are U.S. Coast Guard–certified and highly experienced in navigating Lake Michigan and the Chicago River to ensure a safe and enjoyable charter.
Your safety is our top priority. We closely monitor weather conditions leading up to your charter. If the captain determines that conditions are unsafe before departure, we’ll gladly reschedule or issue a full refund. Once the yacht has departed the dock, the charter is considered executed.
We suggest that guests bring: Bottled Water, Ice, Beverages & Snacks, Sunscreen, Sunglasses, Bathing suit & towel (if swimming), and Phone Chargers. Onboard we provide a cooler, refrigerator, and bathroom for guests to use while underway. Please avoid bringing red or staining liquids, as spills may result in a damage fee.How and when should I get to the Harbor?
We highly recommend using ride-sharing or car services due to limited and/or costly parking. Traffic around the harbors can be significant, especially on holidays or summer weekends. Plan to arrive at least 30 minutes prior to departure (45 minutes on holidays) to allow ample time to walk from drop-off or parking to our dock, check in, get settled, and depart on time.
Yes, all our yachts are equipped with clean and comfortable restroom facilities.
Yes, our yachts are fitted with premium sound systems. You can bring your own playlist or request ours.
Yes. Every charter includes access to Lily Pads and floating platforms for relaxing and enjoying the water. You’re also welcome to bring your own small floaties or water toys if space allows.
Still have questions?
If you don’t see your question here, our team is happy to help make your charter planning effortless.
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