Boats for sale in Chicago Illinois - BoatCrazy

787 boats found within 100 miles out of 11,634 Boats Found

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2026 Sea Ray SPX 190

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 20'
- 2026 / New
- Call for price
Your companion for endless fun. Discover the epitome of sporty sophistication with the new 2026 Sea Ray SPX 190. Designed to deliver exhilarating thrills and timeless style, this a... View Details

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2026 Galeon 435 GTO

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 45'
- 2026 / New
- Call for price
Galeon's new 2026 Galeon 435 GTO is the yacht that can do everything you ask of her and more. This no-compromise model benefits from an entertainment-friendly layout, including a p... View Details

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2026 Sea Ray SPX 210 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 24'
- 2026 / New
- Call for price
Performance and fun. The reimagined 2026 Sea Ray SPX 210 Outboard is designed to be noticed, and delivers the next level of fun, perfect for hosting friends, sharing a casual cruis... View Details

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2026 Sea Ray SDX 270 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 30'
- 2026 / New
- Call for price
Introducing the 2026 Sea Ray SDX 270 Outboard. Outboard power and Sea Ray style. Category-leadign space, plush seating and Sea Ray's legendary attention to detail make the SDX 270... View Details

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2026 Sea Ray SDX 290 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 31'
- 2026 / New
- Call for price
Experience Luxury and Performance with the SDX 290® Outboard. Step aboard the SDX 290® Outboard and immerse yourself in the epitome of luxury and performance. This yacht-certified... View Details

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2026 Sea Ray SDX 270 Surf

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 27'
- 2026 / New
- Call for price
Elegant design and superior performance. The SDX 270 Surf belongs in a class all its own With the capability to pursue full-day adventures, this exquisite surf-ready model takes fu... View Details

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2026 Sea Ray SPX 210

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 22'
- 2026 / New
- Call for price
Designed to be noticed. The sporty 2026 Sea Ray SPX 210, is powered for effortless performance and well-equipped with upscale amenities and innovative technologies for all-day thri... View Details

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2025 Scout 215 Dorado

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 22'
- 2025 / New
- Call for price
Introducing the 2025 Scout 215 Dorado Luxurious Design Step aboard the stunning 2025 Scout 215 Dorado and experience the epitome of luxury on the water. Crafted with precision and... View Details

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2025 Scout 240 Dorado

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 24'
- 2025 / New
- Call for price
Introducing the 2025 Scout 240 Dorado Experience the epitome of luxury and performance with the Scout 240 Dorado, a masterpiece crafted for the ultimate boating enthusiast. Luxurio... View Details

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2025 Scout 255 Dorado

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 26'
- 2025 / New
- Call for price
Experience Luxury On Water with the 2025 Scout 255 Dorado Step aboard the breathtaking 2025 Scout 255 Dorado, a pinnacle of maritime excellence. Equipped with dual Yamaha engines,... View Details

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2013 Pursuit 260C

$119,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Other / Not Classified
- 26'
- 2013 / Used
- $119,900
2013 Pursuit 260C View Details

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$119,900
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2024 Regal 33 EXPRESS

$329,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 33'
- 2024 / Used
- $329,900
2024 Regal 33 EXPRESS View Details

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$329,900
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2005 Sea Ray 280 SUNDANCER

$44,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 28'
- 2005 / Used
- $44,900
2005 Sea Ray 280 SUNDANCER View Details

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$44,900
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1978 Bertram 31

$119,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 31'
- 1978 / Used
- $119,900
Listing Title: 1978 Bertram 31 Unmatched Performance Experience the thrill of the open water with the 1978 Bertram 31, powered by twin MERCRUISER 7.4L engines delivering a combined... View Details

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$119,900
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2006 Regal 3860

$169,985

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 38'
- 2006 / Used
- $169,985
2006 Regal 3860 (Stock #221125) delivers luxury, performance, and timeless elegance in a versatile 38-foot express cruiser. Located at SkipperBud's North Point in Winthrop Harbor,... View Details

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$169,985
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2025 Scout 251 XSS

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 25'
- 2025 / New
- Call for price
Experience Luxury and Performance with the 2025 Scout 251 XSS Embark on thrilling adventures with the futuristic 2025 Scout 251 XSS, boasting unparalleled craftsmanship and cutting... View Details

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2025 Scout 281 XSS

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 28'
- 2025 / New
- Call for price
Introducing the 2025 Scout 281 XSS: Step aboard the luxurious 2025 Scout 281 XSS, a masterpiece of performance and craftsmanship that promises unrivaled excitement on the water. Un... View Details

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2025 Scout 231 XSB

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 23'
- 2025 / New
- Call for price
Introducing the 231 XSB - The Ultimate Fishing Machine The 231 XSB is the latest addition to our bay boat/inshore lineup, designed to take your fishing experience to the next level... View Details

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2025 Scout 175 Sport Dorado

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 17'
- 2025 / New
- Call for price
Introducing the 2025 Scout 175 Sport Dorado Experience the epitome of luxury and performance with the 2025 Scout 175 Sport Dorado. Crafted for those who seek adventure and style on... View Details

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2025 Scout 195 Sport Dorado

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 19'
- 2025 / New
- Call for price
Introducing the 2025 Scout 195 Sport Dorado - the perfect fusion of sportiness and versatility, designed to make your boating experience thrilling and unforgettable. This remarkabl... View Details

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2005 Regal COMMODORE 4260

$199,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 45'
- 2005 / Used
- $199,900
Check out this Regal 4260 Commodore listing from SkipperBud's! Highlighting one of Regal's finest layouts, this cruiser features rebuilt Yanmar engines with under 250 hours since r... View Details

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$199,900
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Showing 85 to 105 of 787 boats found.

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