Boats for sale in Chicago Illinois - BoatCrazy

1,196 boats found within 100 miles out of 14,808 Boats Found

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2025 Sea Ray SLX 260

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Walworth, WI
- Walworth, WI
- 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 SPX 190

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Walworth, WI
- Walworth, WI
- Runabout
- 20' / 0'
- 2025 / New
- Call for price
Calling all water enthusiasts! Sea Ray has the answer to your boating dreams with the dynamic and affordable SPX 190. Designed for those who crave a premium on-water experience wit... View Details

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2025 Sea Ray SPX 190 Outboard

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Walworth, WI
- Walworth, WI
- Runabout
- 22' / 0'
- 2025 / New
- Call for price
Escape the ordinary and dive into adventure with the remarkable SPX 190 Outboard from Sea Ray's prestigious SPX series. This sleek and versatile vessel offers a premium boating exp... View Details

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2025 Sea Ray SDX 250 Outboard

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Walworth, WI
- Walworth, WI
- Runabout
- 25' / 0'
- 2025 / New
- Call for price
Introducing the remarkable 2024 Sea Ray SDX 250 Outboard - the epitome of luxury and performance on the water. This stunning boat is designed to exceed your expectations and offers... View Details

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2025 Sea Ray SDX 270 Outboard

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Walworth, WI
- Walworth, WI
- Runabout
- 27' / 0'
- 2025 / New
- Call for price
Introducing the 2025 Sea Ray SDX 270 Outboard: Step aboard the all-new Sea Ray SDX 270 Outboard and elevate your boating experience to new heights. This 27-foot deck boat is a luxu... View Details

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2025 Sea Ray SLX 350

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Walworth, WI
- Walworth, WI
- 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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2021 Godfrey 235 SFL

$63,995

Walworth, WI
- Walworth, WI
- Pontoon
- 23' / 0'
- 2021 / Used
- $63,995
2021 Godfrey 235 SFL View Details

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$63,995
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2025 Sea Ray SLX 280

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Walworth, WI
- Walworth, WI
- 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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2016 Chaparral 290 Signature

$138,900

South Bend, IN
- South Bend, IN
- Cruiser
- 29' / 9'
- 2016 / Used
- $138,900
Stored Off Site, Shown By Appointment ONLY please! Most cruisers in this size range require you to wake up and disassemble the forward berth if you want to use the dinette for an... View Details

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$138,900
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2019 Supra SA400

$115,000

Delavan, WI
- Delavan, WI
- Ski & Wake
- 25' / 0'
- 2019 / Used
- $115,000
Stock #360586 Reason for selling is "Plans changed". ANY and ALL offers will be put in front of our seller! Submit your offer today! 350HP INDMAR! TRAILER INCLUDED!! READY TO PL... View Details

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$115,000
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1999 Sea Ray 500 Sundancer

$199,000

South Haven, MI
- South Haven, MI
- Express Cruiser
- 50' / 0'
- 1999 / Used
- $199,000
Stock #471094 Video of this vessel available at www [dot] popsells [dot] com/view/471094 Reason for selling is "Has not used enough". ANY and ALL offers will be put in front of... View Details

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$199,000
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2023 Custom Built 25 Hadlee Houseboat

$69,000

South Haven, MI
- South Haven, MI
- Houseboat
- 25' / 8'
- 2023 / Used
- $69,000
Custom Built Houseboat Immerse yourself in stylish and comfortable houseboat living with this newly built 2023 Hadley Houseboat, only the third one built, the other two have b... View Details

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$69,000
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2021 Sylvan L3 LZ

$38,700

Edwardsburg, MI
- Edwardsburg, MI
- Pontoon
- 24' / 0'
- 2021 / Used
- $38,700
Stock #452780 Video of this vessel available at www [dot] popsells [dot] com/view/452780 Reason for selling is "Doesn't use it. Came with the home.". ANY and ALL offers will be... View Details

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$38,700
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2026 Barletta Aria 22 QC

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Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 21' / 0'
- 2026 / New
- Call for price
2026 Barletta ARIA22QC Experience the epitome of luxury with the 2026 Barletta ARIA22QC, a masterpiece meticulously crafted for those who demand nothing but the best. This new beau... View Details

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2026 Barletta Cabrio 24 UE

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Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 25' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Barletta CABRIO24UE Experience unparalleled luxury on the water with the stunning 2026 Barletta CABRIO24UE. Designed with meticulous attention to detail, this... View Details

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2026 Barletta Cabrio 22 UC

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Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 23' / 0'
- 2026 / New
- Call for price
Experience Luxury on Water Introducing the exquisite 2026 Barletta CABRIO22UC, where sophistication meets adventure. Crafted for those who cherish opulence, this vessel elevates yo... View Details

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2026 Barletta Lusso 23 UC

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Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 25' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Barletta LUSSO23UC Embark on unparalleled adventures with the stunning 2026 Barletta LUSSO23UC, where luxury meets performance. This new vessel, located at Ski... View Details

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2026 Barletta Cabrio 22 QC

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Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 23' / 0'
- 2026 / New
- Call for price
Experience Luxury on Water Introducing the 2026 Barletta CABRIO22QC, a stunning embodiment of craftsmanship and performance that will elevate your time on the water. Designed for d... View Details

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2025 Sea Ray SLX 260

$182,956

Pewaukee, WI
- Pewaukee, WI
- Runabout
- 25' / 0'
- 2025 / New
- $182,956
Take advantage of limited-time savings on in-stock boats!Act fast on this limited-time offer! Luxury Redefined: 2025 Sea Ray SLX 260 Sleek Elegance: The Sea Ray SLX 260, a 2025 mar... View Details

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$182,956
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2000 Bayliner 5288 PILOTHOUSE MOTORHOUSE

$339,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 56' / 0'
- 2000 / Used
- $339,995
The "Live Aboard Lifestyle" simply does not get any better than this. Exclusively used in Fresh Water since new, this one owner Bayliner 5288 has been meticulously maintained since... View Details

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$339,995
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1999 Trophy 2352FV

$14,995

Pewaukee, WI
- Pewaukee, WI
- Fishing
- 25' / 0'
- 1999 / Used
- $14,995
2019-Replaced Vinyl. 2016-Replaced Isenglas. Trades considered. View Details

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$14,995
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Showing 799 to 819 of 1,196 boats found.

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