Boats for sale in Chicago Illinois - BoatCrazy

1,168 boats found within 100 miles out of 14,864 Boats Found

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1999 Powerquest 380 AVENGER

$59,995

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Other / Not Classified
- 39' / 9'
- 1999 / Used
- $59,995
1999 Powerquest 38 Avenger for sale. Boat has never seen salt water. This boat has always been stored in doors and has been taken out of water after every use. All systems work wel... View Details

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$59,995
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2016 Regal 2100 SURF

$78,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Bowrider
- 0' / 7'
- 2016 / Used
- $78,000
New to the market is a fantastic option from Regal boats for the watersports enthusiast. This boat is loaded to the gills with just about every option you can imagine. This is a ve... View Details

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$78,000
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2000 Rinker 242 FIESTA VEE

$19,950

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 24' / 9'
- 2000 / Used
- $19,950
Fresh water Lake Michigan boat. Clean cruiser with a trailer included. In water ready for sea trial.Trades considered. View Details

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$19,950
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1998 Stamas 29 EXPRESS

$27,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing
- 29' / 0'
- 1998 / Used
- $27,900
Do not miss this fresh water fishing machine. This hard to find boat is maintained and cared for as you would hope when considering a used boat. Not only has it been cared for, the... View Details

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$27,900
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2026 Cruisers 50GLS OB

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 50' / 0'
- 2026 / New
- Call for price
Luxury Redefined: 2025 Cruisers Yachts 50 GLS Outboard This masterpiece of craftsmanship, style, and performance - the 2025 Cruisers Yachts 50 GLS Outboard - is the epitome of luxu... View Details

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2023 Cruisers 390 EXPRESS COUPE

$579,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 42' / 0'
- 2023 / Used
- $579,000
Just listed: A pristine 100% fresh-water, single owner, 2023 Cruisers Yachts 390 Express Coupe, showroom condition, loaded with all the right premium features. Powered by efficient... View Details

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$579,000
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2004 Doral 360 BOCA GRANDE

$94,995

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 36' / 0'
- 2004 / Used
- $94,995
Experience timeless design and trusted performance with this 2004 Doral 360 Boca Grande, a single owner boat that was meticuously maintained. With 1,500 hours on twin Mercruiser 49... View Details

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$94,995
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2005 Formula 34 PC

$124,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Express Cruiser
- 35' / 0'
- 2005 / Used
- $124,900
Beautiful fresh water Lake Michigan boat. Indoor heated winter storage. Flagship Imron Graphics. Experience the formula performance. Boat is available to view. View Details

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$124,900
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2026 Sea Ray SLX 400 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 42' / 0'
- 2026 / New
- Call for price
Orchestrated excellence. The 2026 Sea Ray's SLX 400 Outboard, "The Entertainer", is an outboard variant of the Innovation Award-winning SLX 400, with massive capacity, deluxe ameni... View Details

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2026 Sea Ray SPX 210 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 24' / 0'
- 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 SPX 210

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 22' / 0'
- 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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2026 Sea Ray SPX 230 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 26' / 0'
- 2026 / New
- Call for price
Powerful performance, agile handling. The 2026 Sea Ray SPX 230 Outboard is built to thrill. It combines the powerful performance and agile handling you'd expect from a world-class... View Details

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2026 Sea Ray SDX 270

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 27' / 0'
- 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 SDX 290 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 31' / 0'
- 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 SPX 190

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 20' / 0'
- 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 Sea Ray SDX 270 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 30' / 0'
- 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 270 Surf

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 27' / 0'
- 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 190 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 22' / 0'
- 2026 / New
- Call for price
The ultimate in fun. Discover the water like never before with the 2026 Sea Ray SPX 190 Outboard. Combining sleek aesthetics with advanced technology, this model redefins the moder... View Details

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2026 Sea Ray SDX 290

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 29' / 0'
- 2026 / New
- Call for price
Built for fun, introducing the 2026 Sea Ray SDX 290. When an active family loves water sports, they generall want to share their good times with friends. That's where the SDX 290 c... View Details

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2026 Sea Ray SLX 350

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 36' / 0'
- 2026 / New
- Call for price
Luxury elevated. Sea Ray's SLX 350 hosts an array of features designed for an excellent on-water experience and optimal performance. Powered by twin Mercury MerCruiser 6.2L engines... View Details

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2026 Sea Ray SLX 350 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 38' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Sea Ray SLX 350 Outboard, luxury elevated. The SLX 350 Outboard incorporates top SLX features and enhancements that set the standard for large dayboats. The SL... View Details

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Showing 22 to 42 of 1,168 boats found.

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