Book Your Yacht Experience at The Playpen Chicago
Book a Yacht Charter, Find a USCG Certified Captain at the Playpen in Chicago and Lake Michigan
Browse ExperiencesWhy Playpen Chicago Yachts
Book fun, fast. Browse commercially-insured yachts ready for Chicago’s Playpen. Transparent pricing, USCG-certified captains, and instant booking mean less time planning and more lake time.
Browse Yacht AvailabilityList Your Yacht
Got a charter boat? List in minutes, set your hourly rates, and reach Chicago’s biggest lake crowd. Choose each captain you allow on your boat. Bookings, payouts, and support: handled.
List Your YachtUSCG Captain Signup
USCG captain? Select the boats you're approved to captain, set your rates, pick your schedule, and get paid quickly and directly for each trip.
Captain OnboardingBecome an Add-On Partner
Do you offer extras like DJs, catering, yacht products, or on-board experiences? Join us as an add-on partner and put your service in front of every renter at checkout. Get listed, get booked, get paid.
Add-on Partner EnquiryFeatured Experiences
From skyline sunsets to high-energy Playpen parties, our curated experiences turn a simple boat rental into an unforgettable story. Swipe through the carousel below to browse custom itineraries—each bundled with the perfect mix of add-ons and insider perks—so you can book the vibe, not just the vessel.
What is Playpen Chicago?
Playpen Chicago is the definitive hub for exclusive yacht rentals, premium captain services, and unforgettable entertainment experiences on Lake Michigan's iconic Playpen area. Combining the luxury of private boat charters with top-tier USCG-certified captains, it transforms a day on the water into a seamless, memorable adventure. Beyond just rentals, Playpen Chicago curates nightlife events and personalized outings, connecting boat enthusiasts, partygoers, and entertainment seekers with Chicago's most vibrant waterfront scene. Whether you're hosting an intimate sunset cruise, a lively party, or an upscale corporate event, Playpen Chicago delivers exceptional experiences tailored to every occasion.