Boats for sale in Chicago Illinois - BoatCrazy

1,207 boats found within 100 miles out of 14,736 Boats Found

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2026 Sailfish 316 DC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 33' / 0'
- 2026 / New
- Call for price
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 241 CC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 24' / 0'
- 2026 / New
- Call for price
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 272 CC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 27' / 0'
- 2026 / New
- Call for price
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 242 CC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 24' / 0'
- 2026 / New
- Call for price
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 Yamaha 222 FSH Sport E

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 0' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha 222 FSH Sport E, built with value and versatility. The 222 FSH Sport E redefines excellence in 22-foot center console boats with its powerful twin-engin... 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 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 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 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 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 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 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 AR220

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 22' / 0'
- 2026 / New
- Call for price
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 275SE

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 27' / 0'
- 2026 / New
- Call for price
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 222S

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 22' / 0'
- 2026 / New
- Call for price
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 SX250

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25' / 0'
- 2026 / New
- Call for price
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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1998 Viking 52 FLYBRIDGE

$249,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 51' / 0'
- 1998 / Used
- $249,900
For sale: A stunning 1998 Viking Yachts 52 Flybridge (VSC 52 Flybridge), a rare gem and precursor to today’s Princess Yachts. Powered by robust CAT 3196TA engines with their 2,000-... View Details

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$249,900
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2017 Formula 350 CBR

$275,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Bowrider
- 35' / 0'
- 2017 / Used
- $275,000
!00% Fresh water, with 515 hours on pampered Merc 300 HP Verado JPO engines (joystick operated) It has a Garmin 7610 GPS plotter, shore power, heat and air in the cabin, vacuflush... View Details

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$275,000
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2022 Cruisers 38 GLS

$604,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 37' / 0'
- 2022 / Used
- $604,900
The ultimate family or entertainer's day boat! This stunning 2022 Cruisers Yachts 38 GLS is perfect for those who love to spend time on the water, offering luxurious amenities and... View Details

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$604,900
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2025 Aviara AV40 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 42' / 0'
- 2025 / New
- Call for price
2025 Aviara AV40 Outboard Experience the epitome of luxury and performance with the 2025 Aviara AV40 Outboard. Crafted with meticulous attention to detail, this stunning vessel is... View Details

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2025 Aviara AV36

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 37' / 0'
- 2025 / New
- Call for price
Introducing the 2025 Aviara AV36: Experience the ultimate luxury on water with the Aviara AV36, a masterpiece of design and performance. Luxurious Craftsmanship: An exquisite blend... View Details

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Showing 106 to 126 of 1,207 boats found.

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