Book Your Luxury Yacht Experience! PLAYPEN Chicago & more!
The Nineteenth Hull SunDancer 380 Yacht
The Nineteenth Hull SunDancer 380 Yacht
The Nineteenth Hull SunDancer 380 Yacht
Relax and unwind with our luxury yacht in Chicago, the Sea Ray SunDancer. This stunning yacht features a full kitchen, a large cabin, and ample seating, making it perfect for your party, celebration, or just a great day out on the water.
Whether you're looking for a Chicago boat rental for a bachelorette party or simply want to enjoy the PLAYPEN Chicago with friends, our yacht is an excellent choice. Boat prices start at $325/hr on weekdays and $375/hr on weekend.
Captain and crew are extra ($150-$180/hr), with special events priced higher. Don't miss the chance to rent a boat in Chicago on Lake Michigan!
Tilly's Dream: Corporate & more for up to 34 guests! Starting at $825/hr
The Nineteenth Hull SunDancer 380 Yacht
The Nineteenth Hull SunDancer 380 Yacht
Book this boat for bachelorette parties, birthday parties, and family events!
Want to enhance your corporate team's productivity? Tilly's Dream offers a unique and inspiring setting for up to 34 of your colleagues to relax, network, and create lasting memories. Check out Tilly's Dream on Insta.
Want to see a show at the Salt Shed? Let us create the perfect on-water concert experience.
Or let's go to the PLAYPEN Chicago!
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Gorgeous 50-foot yacht $375/hr weekdays and $425/hr weekends
The Nineteenth Hull SunDancer 380 Yacht
Gorgeous 50-foot yacht $375/hr weekdays and $425/hr weekends
You and 12 of your guests can indulge in luxury on this HUGE yacht, making it the perfect Chicago boat rental for a bachelorette party or any special occasion!
Ready to elevate your next on-water experience? This luxury yacht in Chicago is also ideal for birthday parties and family events! Enjoy the fun with included water toys!
Please note that a captain and crew are required at an additional charge of $180 per hour. Don't miss out on the best Playpen Chicago boat rentals—rent a boat in Chicago on Lake Michigan today!
Mia' Amore: Beautiful 2024 Chapparal 307 SSX
Spectacular Galeon 430-Sky Experience luxury redefined.
Gorgeous 50-foot yacht $375/hr weekdays and $425/hr weekends
Looking for a perfect boat for a day out on the water? This luxury SPEEDBOAT in Chicago is ideal for accommodating a party of up to 10 people, making it a fantastic choice for an intimate bachelor/bachelorette party or a family outing!
With affordable rates starting at just $250/hr, plus an extra fee for the captain ($150/hr), you won't find better value.
Want to see more? Check out this awesome boat and our PLAYPEN Chicago boat rentals on our Instagram page: Check out Mia' Amore on Insta!
LunaSEA Sea Ray SunDancer Perfect for 10 People
Spectacular Galeon 430-Sky Experience luxury redefined.
Spectacular Galeon 430-Sky Experience luxury redefined.
Explore the beauty of the Chicago waterways with this luxury yacht perfect for up to 10 guests. If you're looking for a perfect option for on-water parties, leisure, or family outings, consider a luxury yacht in Chicago.
LunaSea offers an incredible experience that you won't want to miss—especially if you're planning a Chicago boat rental for an intimate & special bachelor/bachelorette party or birthday party!
Rates start at $250 hour plus Captain. Captain rate $150/hour
Book your rental today and create lasting memories on the water, whether you choose to rent a boat in Chicago Lake Michigan or enjoy the popular PLAYPEN Chicago boat rentals.
Spectacular Galeon 430-Sky Experience luxury redefined.
Spectacular Galeon 430-Sky Experience luxury redefined.
Spectacular Galeon 430-Sky Experience luxury redefined.
Experience one of Chicago's hottest and most unique yachts with our luxury yacht Chicago offerings. Immerse yourself in luxury as you explore the stunning waters of Lake Michigan! Boat prices start at $350/hr on weekdays and $400/hr on weekends, with higher rates for special events.
Unleash the Galeon Lifestyle with a Galeon yacht charter, which is more than just a boat trip; it's an escape into a world of unparalleled elegance. Perfect for a memorable celebration, this is the ideal choice for a Chicago boat rental for a bachelorette party.
You will love sitting on the sky bridge! The yacht also includes a lily pad and other water toys for endless fun.
Please note that the captain and crew are available for an additional cost of $180/hour. Don't miss out on the chance to rent a boat in Chicago on the beautiful Lake Michigan and enjoy unforgettable moments with friends!
Our Favorite Yachts & Boats: Call Dani to book
Chicago's Most Exclusive Yachts
Chicago's Most Exclusive Yachts
Chicago's Most Exclusive Yachts
Some luxury yachts in Chicago are too exclusive to advertise publicly! Experience the ultimate luxury yacht Chicago has to offer, with boat rentals starting at $1500/hour.
Whether you're looking to rent a boat in Chicago Lake Michigan for a special occasion or seeking the perfect option for an exclusive bachelorette party, you must call to book!
Escape into a world of unparalleled elegance with our PLAYPEN Chicago boat rentals.
Please note that USCG regulations allow only 13 people on these vessels, regardless of boat size.
2022 Sea Ray SLX 350
Chicago's Most Exclusive Yachts
Chicago's Most Exclusive Yachts
The 2022 Sea Ray SLX 350 is a premium bowrider, perfect for those seeking a luxurious and high-performance boating experience, especially for events like a bachelorette party in Chicago. This boat is ideal for anyone wanting to be noticed on Chicago's waters. Chartering this luxury yacht in Chicago offers a top-tier amenities experience.
Experience luxurious comfort!
- Spacious social cockpit area with premium seating, perfect for gatherings.
- Port Hideaway cabin with air conditioning for relaxation, ideal for a serene escape.
- Concealable transom loungers for added comfort while enjoying the views.
- Sleek lines and high-end finishes create a head-turning appearance, making it a standout choice among Playpen Chicago boat rentals.
- Designed to provide a high-end social experience, perfect for those who want to rent a extraoridnary boat in Chicago on Lake Michigan.
Our Classic Chris Craft
Chicago's Most Exclusive Yachts
Our Classic Chris Craft
Escape to the Past in Style with a Luxury Yacht in Chicago! Rent a Classic Chris Craft and experience the thrill of cruising Lake Michigan or the Chicago River aboard a vintage 40-foot Chris Craft. This iconic vessel provides a unique and unforgettable experience for you and up to 12 guests, making it a perfect choice for a Chicago boat rental for a bachelorette party or a family gathering.
Enjoy the following features:
Luxurious Interior: Relax in comfort with plush seating and modern amenities.
Panoramic Views: Soak in the stunning scenery from the spacious deck.
Personalized Service: Our experienced captain ensures a safe and enjoyable journey.
Perfect for:
- Special occasions (weddings, birthdays, anniversaries)
- Corporate events
- Family outings
- Romantic getaways
Don't miss out on the chance to rent a boat in Chicago on Lake Michigan and book your charter now to create memories that will last a lifetime. And yes, we can take you to the PLAYPEN Chicago on this boat rental!
2020 Sea Ray Yacht
Day or Overnight Trips to South Haven, Michigan
Our Classic Chris Craft
Sea Ray SLX400
Experience luxury on the water with this stunning yacht, perfect for your next Chicago boat rental for a bachelorette party. This luxury yacht in Chicago will undoubtedly turn heads and provide the ultimate in style and comfort. It's ideal for overnight excursions to Michigan or Wisconsin, making it a versatile choice for your adventures.
Prices start at $850/hr, with outings customized to your exact specifications. Captain is extra, ensuring your experience is tailored for fun on the Playpen Chicago boat rentals or when you choose to rent a boat in Chicago Lake Michigan.
Day or Overnight Trips to South Haven, Michigan
Day or Overnight Trips to South Haven, Michigan
Day or Overnight Trips to South Haven, Michigan
The charming and beautiful town of South Haven, Michigan, is known for its pristine beaches, quaint shops, and delicious local cuisine. Let us plan a special adventure for you. While you are there, check out our friends at Gull Lake Marine and the Michigan Maritime Museum.
A Yacht Trip from Chicago to South Haven: A Luxurious Escape
A yacht trip from the bustling metropolis of Chicago to the charming coastal town of South Haven offers an unparalleled experience. Imagine trading the city's concrete jungle for the open expanse of Lake Michigan. For those planning a special event, consider a Chicago boat rental for a bachelorette party, where you can enjoy the stunning views along the way.
Whether you're seeking adventure, relaxation, or a combination of both, a yacht trip from Chicago to South Haven is the perfect escape. If you're looking to elevate your experience, consider luxury yacht Chicago options, or for a more casual outing, explore playpen Chicago boat rentals. Regardless of your choice, renting a boat in Chicago's Lake Michigan will surely make your trip memorable.
Sailing in Saugatuck, Michigan
Day or Overnight Trips to South Haven, Michigan
Day or Overnight Trips to South Haven, Michigan
Want to get away? Picture yourself cruising under the vast Michigan sky on a sailboat, sails billowing in the cool lake breeze, surrounded by the stunning backdrop of Saugatuck, Michigan. It's only 2 short hours from Chicago, but you feel like you are a million miles away.
Check out all the things to do in Saugatuck, Michigan's Art Coast! Packages available for $60 per person for up to 6 guests.
Want a sneak peek? Check out the beautiful Kalamazoo River on our Instagram page!