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Tilly's Dream: Corporate & More! Accommodates 34 Guests!

Book this boat for bachelorette parties, birthday parties, and family events for as low as $800 per hour, including captain and crew!

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!

Tilly's includes awesome water toys!

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350 Sundancer, a motor boat with a sleek design and a spacious interior
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Mia' Amore: Beautiful 2024 Chaparral 307 SSX

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!

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350 Coupe, with a sofa, table, cupboards, sink, tap, and other objects on the left side

Gorgeous 50-Foot Yacht: Huge! Indulge in Luxury!

You and 12 of your guests indulge in luxury on this HUGE yacht, making it the perfect Chicago boat rental for a bachelorette party, birthday party, family event, or any special occasion!

Enjoy the fun with included water toys!

$375/hr weekdays, $500/hr Saturdays. $475/hr Sundays (special events $600/hr).

4-hour minimum for your pleasure!

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!

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LunaSEA Sea Ray SunDancer: Perfect for 9 People

Explore the beauty of the Chicago waterways with this luxury yacht perfect for up to 9 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 $300 an hour plus the captain. The captain's rate is $150/hour.

Book your rental today and create lasting memories on the water, whether you choose to rent a boat in Chicago's Lake Michigan or enjoy the popular Playpen Chicago boat rentals.

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Sea Ray SunDancer 350

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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 $300/hr on weekdays and $425/hr on weekends.

The 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!

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Premium Yacht & Boat Charters

Our Favorite Yachts & Boats: Call Dani to Book

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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 $800/hour.

Whether you're looking to rent a boat in Chicago's 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.

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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 Lake Michigan! The Galeon Yacht is priced at $650/hr most weekdays and $800/hr on weekends and for Wednesday night fireworks. $1000 per hour for special events and holidays.

Please note that the captain and crew are an additional cost of $180/hour. Don't miss out on the chance to rent a boat in Chicago on beautiful Lake Michigan and enjoy unforgettable moments with friends!

Unleash the Galeon lifestyle with a Galeon yacht charter! A perfect Chicago boat rental for a bachelorette party or other special event.

You will love sitting on the skybridge! The yacht also includes a lily pad and other water toys for endless fun.

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Black and white 260 Sundancer boat docked at a dock surrounded by other boats on the water
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270 Sundancer boat docked at a dock with an American flag on it, surrounded by other boats on the water
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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, and 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!

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Chicagoland Fishing

Experience the thrill of a world-class fishing expedition without the logistical headaches of the city. Departing from Hammond Marina, our charters offer the perfect escape just 10 convenient miles from downtown Chicago. Skip the expensive garages and frantic traffic; here, you’ll enjoy free, secure parking just steps from the dock, allowing you to transition from the skyline to the shoreline in minutes. It is the premier gateway to Lake Michigan for those who value both their time and their catch.

Once on the water, you’ll discover why these waters are legendary for trophy-sized salmon and trout. Our expert captains guide you to the most productive honeyholes where the lake's current creates a vibrant ecosystem for massive Coho, King Salmon, and Steelhead. Whether you are a seasoned angler chasing a personal best or a family looking for an unforgettable day on the lake, our Hammond-based charters provide a high-energy, professional fishing experience with the iconic Chicago skyline as your backdrop.

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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.

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Sailing in Saugatuck, 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 are available for $60 per person for up to 6 guests.

Want a sneak peek? Check out the beautiful Kalamazoo River on our Instagram page!

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