Boats for sale in Chicago Illinois - BoatCrazy

768 boats found within 100 miles from Chicago, Illinois

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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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2026 Sea Ray SDX 250

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25'
- 2026 / New
- Call for price
Elegant design. Superior performance. The 2026 Sea Ray SDX is engineered to offer exceptional capability for full days spend on the water. This adaptable sterndrive model features... 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 250 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 28'
- 2026 / New
- Call for price
True leisure and maximum comfort. The 2026 Sea Ray SDX 250 Outboard is built for true leisure and comfort. With exceptional storage space, enhanced ergonomic seating, and dual 9" d... View Details

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2026 Sea Ray SDX 270

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 27'
- 2026 / New
- Call for price
Experience Luxury and Performance with the 2026 Sea Ray SDX 270. Introducing the all-new magnificent 2026 Sea Ray SDX 270, setting the standard for style and performance on the wat... View Details

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2026 Sea Ray SLX 310 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 34'
- 2026 / New
- Call for price
Share the thrill. Expansive social areas, a standard wet bar and plenty of available seating means hosting friends and family has been more comfortable. Aboard the 2026 Sea Ray SLX... View Details

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2026 Sea Ray SLX 310

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 32'
- 2026 / New
- Call for price
The 2026 Sea Ray SLX 310: Luxury and Style Redefined. The 2026 Sea Ray SLX 310 sets the standard for luxury and style on the water. This exceptional boat combines cutting-edge desi... View Details

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Showing 106 to 126 of 768 boats found.

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