Boats for sale in Chicago Illinois - BoatCrazy

1,233 boats found within 100 miles out of 14,769 Boats Found

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2026 Yamaha 252SD

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25' / 0'
- 2026 / New
- Call for price
The future is now with the 2026 Yamaha 252SD. Introducing DRiVE X, the next evolution of Yamaha's DRiVE technology, revolutionizing boat maneuverability. With this advanced system,... View Details

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2026 Yamaha SX250

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25' / 0'
- 2026 / New
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Exceed your expectations with the 2026 Yamaha SX250. With 400 horsepower, an innovative hull design, ample storage, and a functional layout, this boat is an unbeatable value. Key F... View Details

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2026 Yamaha 222S

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 22' / 0'
- 2026 / New
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The 2026 Yamaha 222S, timeless style, premium performance. The 222S combines timeless styling, premium refinements, and class-leading performance in an affordable 22-foot package.... View Details

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2026 Yamaha 275SE

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 27' / 0'
- 2026 / New
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Introducing the 2026 Yamaha 275SE, elevaing boating luxury. Experience an exceptional blend of comfort, luxury, and distinctive design. Key Features Luxury and Performance - Step i... View Details

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2026 Yamaha AR220

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 22' / 0'
- 2026 / New
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Introducing the 2026 Yamaha AR220, value-packed watersports fun. Offering the perfect blend of value, versatility, and convenience in an affordable 22-foot package. Key Features Pe... View Details

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2026 Yamaha SX220

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 22' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha SX220, unmatched value, versatility, and affordability. With its roomy cockpit, abundant storage, and fuel-efficient dual engines, this boat offers exce... View Details

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2026 Yamaha AR195

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 19' / 0'
- 2026 / New
- Call for price
Introducing your 2026 Yamaha AR195, supercharge your Saturdays. Enjoy unparalleled supercharged performance, standout styling, and incredible value, all enhanced by a watersports t... View Details

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2026 Yamaha AR250

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25' / 0'
- 2026 / New
- Call for price
Experience total wakesports excitement with the 2026 Yamaha AR250. Experience unparalleled value for its size with the AR250. Its stylish watersports design, powered by robust 1.9L... View Details

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2026 Yamaha 275SD

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 27' / 0'
- 2026 / New
- Call for price
Attainable luxury, technology, and performance-meet the 2026 Yamaha 275SD. The 275SD redefines what's possible in a 27-foot jet boat, offering attainable luxury, cutting-edge techn... View Details

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2026 Yamaha AR190

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 19' / 0'
- 2026 / New
- Call for price
The 2026 Yamaha AR190, watersports ready. Effortless ownership meets advanced features and stylish design at a great value. Watersports-ready, the AR190 is easy to own and apprecia... View Details

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2026 Yamaha 222SD

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 21' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha 222SD, in a league of its own. Featuring award-winning handling technology and Yamaha's premium features, the 222SD is in a league of its own. Key Featu... View Details

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2026 Sailfish 245 DC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 24' / 0'
- 2026 / New
- Call for price
With comfortable seating for 12, a spacious step-down head and an optiona cockpit galley, the 245 dual console is designed for active families as well as serious offshore anglers.... View Details

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2026 Sailfish 360 CC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 39' / 0'
- 2026 / New
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The flagship 360 center console combines unsurpassed quality and state-of-the-art technology with a layout and features designed for maximum versatility. Fish, play, cruise or ente... View Details

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2026 Sailfish 242 CC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 24' / 0'
- 2026 / New
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Designed and built for offshore anglers, the 242 center console features the Sailfish VDS hull, ensuring smooth, powerful performance. With its larger console headspace, ample seat... View Details

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2026 Sailfish 272 CC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 27' / 0'
- 2026 / New
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The 2026 Sailfish 272 center console offers next-level comfort with ample fish-fighting room. Enjoy smooth, powerful performance courtesy of the 6th-generation VDS hull design, and... View Details

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2026 Sailfish 241 CC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 24' / 0'
- 2026 / New
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With its sleek, dynamic profile and 6th generation VDS hull, combined with a highly functional layout and long-lasting Sailtech Construction, the 241 center console is a powerful f... View Details

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2026 Sailfish 316 DC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 33' / 0'
- 2026 / New
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The new 316 dual console is a versatile family fishing boat that checks all the boxes: comfort, safety, quality and reliability. Well-equipped for a range of activities, the 316 DC... View Details

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2026 Sailfish 312 CC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 31' / 0'
- 2026 / New
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The all-new 2026 Sailfish center console offers an incredible VDS hull design for fuel efficiency and comfort, a striking appearance, ample space, and prioritized safety. It has ev... View Details

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2026 Sailfish 276 DC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 29' / 0'
- 2026 / New
- Call for price
Incredible versatility and comfort are hallmarks of the 276 dual console. A 6th-generation VDS hull ensures a soft, dry ride, while the spacious, ergonomic deck design and an array... View Details

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2026 Yamaha 195S

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 19' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha 195S, affordable luxury features at 19-feet. High-tech features, sleek design, and top-notch performance create the ultimate affordable 19-foot boat pac... View Details

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2026 Yamaha SX195

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 19' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha SX195, built to elevate your weekends. Experience unrivaled supercharged performance, striking styling, and exceptional value in its class. Key Features... View Details

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Showing 64 to 84 of 1,233 boats found.

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