Boats for sale in Chicago Illinois

1,170 boats found within 100 miles out of 14,788 Boats Found

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2024 Aviara AV32

$369,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Bowrider
- 32' / 10'
- 2024 / New
- $369,000
Contact us to find out ALL available savings! Take advantage of limited-time savings on in-stock boats!Aviara has redefined the modern day boat to bring you true luxury. This is th... View Details

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$369,000
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1999 Silverton 322AFTCABIN

$49,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 32' / 0'
- 1999 / Used
- $49,900
Great opportunity to own a fresh water, 32' Silverton aft cabin. 460 hours on upgraded 454 EFI Crusaders. Newer canvas and radar/plotter, and fantastic staterooms, and salon/galley... View Details

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$49,900
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2018 Scout 275 LXF

$189,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing
- 27' / 9'
- 2018 / Used
- $189,000
75 hours on 200 Yamahas, all fresh water. The 275LXF dominated that segment, and for good reasons. It's a perfect combo of comfort and performance. The Garmin Radar/Plotter is new,... View Details

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$189,000
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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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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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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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2013 Cruisers 41 CANTIUS

$299,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 41' / 13'
- 2013 / Used
- $299,000
Fresh water hours on this popular 41' Cantius, with Volvo IPS 500's, with pods and joystick docking. Notable options on this particular one, starts with a grill at the stern, upgra... View Details

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$299,000
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2022 Ranger 2360 BAY

$124,500

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 23' / 0'
- 2022 / Used
- $124,500
Beautiful Lake Michigan fresh water boat. Indoor heated winter storage, indoor summer storage-in/out service. Boat and trailer ready for immediate use. Trades considered. View Details

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$124,500
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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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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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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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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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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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2025 Scout 277 Dorado

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 28' / 0'
- 2025 / New
- Call for price
Experience Luxury with the 2025 Scout 277 Dorado Step into a world of opulence with the Scout 277 Dorado, a masterpiece of marine engineering that promises unmatched performance an... View Details

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2025 Sea Ray SLX 260 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 26' / 0'
- 2025 / New
- Call for price
Discover the Sea Ray SLX 260 Outboard - An Award-Winning Masterpiece Step aboard the Sea Ray SLX 260 Outboard and prepare to be amazed. Winner of the 2023 Miami Innovation Award in... View Details

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2025 Sea Ray SLX 280

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 29' / 0'
- 2025 / New
- Call for price
Discover the Ultimate in Luxury and Performance with the 2025 Sea Ray SLX 280 Prepare to be captivated by the sheer elegance and top-tier performance of the 2025 Sea Ray SLX 280. M... View Details

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2025 Sea Ray SLX 260

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 26' / 0'
- 2025 / New
- Call for price
Discover the New SLX 260Experience the ultimate blend of luxury and performance with the all-new SLX 260 boat. Crafted with precision and attention to detail, this vessel is design... View Details

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2025 Sea Ray SLX 260 Surf

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Ski & Wake
- 26' / 0'
- 2025 / New
- Call for price
Introducing the SLX 260 SurfDiscover the SLX 260 Surf, where luxury meets innovation in wakesurfing technology. This exceptional boat combines the elegance of the SLX 260 with cutt... View Details

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2025 Sea Ray SLX 280 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 0' / 0'
- 2025 / New
- Call for price
Introducing the Sea Ray SLX 280 Outboard Experience luxury and performance like never before with the Sea Ray SLX 280 Outboard. This stylish and modern boat is designed to elevate... View Details

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2025 Sea Ray SLX 350

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 35' / 0'
- 2025 / New
- Call for price
The 2025 Sea Ray SLX 350: Embark on a journey of luxury, power, and performance with the 2025 Sea Ray SLX 350. This exceptional boat is the perfect combination of style and functio... View Details

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2025 Sea Ray SLX 400

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 40' / 0'
- 2025 / New
- Call for price
Discover the SLX 400: The SLX 400 is the pinnacle of luxury and performance in the world of sport boats. Impeccably crafted and ingeniously designed, this vessel is a testament to... View Details

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