Boats for sale in Chicago Illinois

1,170 boats found within 100 miles out of 14,815 Boats Found

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2026 Sea Ray SDX 290

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Pewaukee, WI
- Pewaukee, WI
- 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 SDX 270 Outboard

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Pewaukee, WI
- Pewaukee, WI
- 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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Pewaukee, WI
- Pewaukee, WI
- 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 Mastercraft XT22

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Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22' / 0'
- 2026 / New
- Call for price
Introducing the 2025 Mastercraft XT22 Experience a new level of luxury and performance with the Mastercraft XT22. This sleek vessel combines cutting-edge design with unrivaled craf... View Details

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2026 Sea Ray SPX 230 Outboard

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Pewaukee, WI
- Pewaukee, WI
- 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 SPX 210 Outboard

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Pewaukee, WI
- Pewaukee, WI
- 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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Pewaukee, WI
- Pewaukee, WI
- 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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2025 Barletta Lusso

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 0' / 0'
- 2025 / New
- Call for price
Introducing the 2025 Barletta Lusso Experience the epitome of luxury on the water with the 2025 Barletta Lusso. Luxurious Craftsmanship Step aboard and immerse yourself in the stun... View Details

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2005 Sea Ray 240 SUNDECK

$21,498

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 24' / 0'
- 2005 / Used
- $21,498
Embark on endless adventures with the 2005 Sea Ray 240 Sundeck, a deck boat that's primed and ready for her next adventure. Boasting an array of amenities including bow and transom... View Details

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$21,498
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2024 Mastercraft X24

$215,912

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 24' / 9'
- 2024 / New
- $215,912
Contact us to find out ALL available savings! Take advantage of limited-time savings on in-stock boats!All Sale and/or Clearance Prices include all rebates and incentives.Command t... View Details

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$215,912
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2021 Mastercraft NXT24

$87,832

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 24' / 0'
- 2021 / Used
- $87,832
The 2021 MasterCraft NXT24 is the ultimate combination of luxury, performance, and versatility for water sports enthusiasts. Designed to provide an exhilarating experience, this 24... View Details

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$87,832
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2023 Mastercraft X22

$159,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22' / 9'
- 2023 / New
- $159,995
Contact us to find out ALL available savings! Take advantage of limited-time savings on in-stock boats!All Sale and/or Clearance Prices include all rebates and incentives. Now is t... View Details

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$159,995
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2011 Malibu RESPONSE

$36,995

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 21' / 0'
- 2011 / Used
- $36,995
2011 Malibu RESPONSE View Details

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$36,995
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2024 Scout 195 Sportfish

$70,330

Pewaukee, WI
- Pewaukee, WI
- Fishing Sportfish / Convertible
- 19' / 9'
- 2024 / New
- $70,330
Contact us to find out ALL available savings! Take advantage of limited-time savings on in-stock boats!All Sale and/or Clearance Prices include all rebates and incentives. Whether... View Details

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$70,330
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2024 Harris Crowne 250

$217,034

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 28' / 9'
- 2024 / New
- $217,034
Contact us to find out ALL available savings! Take advantage of limited-time savings on in-stock boats!HARRIS 250 CROWNE SL All Sale and/or Clearance Prices include all rebates and... View Details

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$217,034
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2024 Sea Ray SLX 260 Surf

$206,582

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 26' / 0'
- 2024 / New
- $206,582
Contact us to find out ALL available savings! Take advantage of limited-time savings on in-stock boats!All Sale and/or Clearance Prices include all rebates and incentives.Discover... View Details

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$206,582
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2024 Mastercraft XT25

$173,240

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 25' / 9'
- 2024 / New
- $173,240
Contact us to find out ALL available savings! Take advantage of limited-time savings on in-stock boats!All Sale and/or Clearance Prices include all rebates and incentives.Introduci... View Details

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$173,240
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2023 Mastercraft NXT23

$117,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 23' / 8'
- 2023 / New
- $117,995
Contact us to find out ALL available savings! Take advantage of limited-time savings on in-stock boats!All Sale and/or Clearance Prices include all rebates and incentives.The NXT23... View Details

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$117,995
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2024 Scout 175 Dorado

$51,908

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 17' / 8'
- 2024 / New
- $51,908
Contact us to find out ALL available savings! Take advantage of limited-time savings on in-stock boats!All Sale and/or Clearance Prices include all rebates and incentives.Whether t... View Details

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$51,908
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2025 Mastercraft NXT20

$109,114

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20' / 8'
- 2025 / New
- $109,114
Take advantage of limited-time savings on in-stock boats!Explore the Waves in Style with the NXT20 Discover the perfect combination of affordability and excitement with the NXT20 b... View Details

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$109,114
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2025 Harris Cruiser 210

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 24' / 9'
- 2025 / New
- Call for price
Take advantage of limited-time savings on in-stock boats!Invite your friends waterskiing, take the kids for a sun-soaked day of cruising, or escape alone and cast a line. No matter... View Details

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