Boats for sale in Chicago Illinois - BoatCrazy

1,187 boats found within 100 miles out of 13,653 Boats Found

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2026 Sea Ray SPX 190 Outboard

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Walworth, WI
- Walworth, WI
- Runabout
- 22'
- 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 Outboard

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Walworth, WI
- Walworth, WI
- Runabout
- 31'
- 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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Walworth, WI
- Walworth, WI
- Runabout
- 20'
- 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 290

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Walworth, WI
- Walworth, WI
- Runabout
- 29'
- 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 Surf

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Walworth, WI
- Walworth, WI
- 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 SDX 270 Outboard

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Walworth, WI
- Walworth, WI
- 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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2004 Chaparral 280 SSi

$44,000

Waterford, WI
- Waterford, WI
- Bowrider
- 28'
- 2004 / Used
- $44,000
Stock #487201 Video of this vessel available at www [dot] popsells [dot] com/view/487201 Reason for selling is "Buying a smaller boat". This Chaparral has been on the market for... View Details

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$44,000
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2019 Supra SA400

$115,000

Delavan, WI
- Delavan, WI
- Ski & Wake
- 25'
- 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'
- 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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2021 Sylvan L3 LZ

$38,700

Edwardsburg, MI
- Edwardsburg, MI
- Pontoon
- 24'
- 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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2024 Mastercraft X24

$204,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 24'
- 2024 / New
- $204,995
Contact us to find out ALL available savings! All Sale and/or Clearance Prices include all rebates and incentives. Command the surf with the machine that was named most innovative... View Details

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$204,995
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2024 Mastercraft XT25

$173,240

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 25'
- 2024 / New
- $173,240
Contact us to find out ALL available savings! All Sale and/or Clearance Prices include all rebates and incentives. Introducing the all-new XT25. Completely redesigned from the hull... View Details

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$173,240
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2025 Mastercraft NXT20

$109,114

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20'
- 2025 / New
- $109,114
Contact us to find out ALL available savings! Explore the Waves in Style with the NXT20 Discover the perfect combination of affordability and excitement with the NXT20 boat. Measur... View Details

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$109,114
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2025 Mastercraft XT22

$175,880

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22'
- 2025 / New
- $175,880
Contact us to find out ALL available savings! Versatility and flexibility are important when you want to please the crowd. The XT22 has you covered with seating for 16 and a spacio... View Details

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$175,880
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2025 Mastercraft NXT21

$120,815

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 21'
- 2025 / New
- $120,815
Contact us to find out ALL available savings! The fresh new MasterCraft NXT22 is big news. One of our most popular boats ever has a brand new design and updates from tip to tail. T... View Details

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$120,815
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2025 Harris 250 Cruiser

$77,167

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 26'
- 2025 / New
- $77,167
Contact us to find out ALL available savings! Embark on Luxury Adventures with the 2025 Harris 250 Cruiser SL Tri-Toon Experience effortless power and performance with the MERCRUIS... View Details

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$77,167
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2025 Mastercraft XSTAR

$355,553

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 23'
- 2025 / New
- $355,553
Act fast on this limited-time offer! Experience Unmatched Performance Introducing the 2025 Mastercraft XSTAR, where cutting-edge engineering meets exhilarating performance. This st... View Details

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$355,553
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2026 Scout 188 Sportfish

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Pewaukee, WI
- Pewaukee, WI
- Fishing Center Console
- 19'
- 2026 / New
- Call for price
From the company that has brough many firsts to the coastal fishin boat segment, they introduce their new 188 Sportfish. This model sets a new bar by incorporating many features no... View Details

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2026 Scout 195 Sportfish

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Pewaukee, WI
- Pewaukee, WI
- Fishing Center Console
- 19'
- 2026 / New
- Call for price
This 19-footer measures 19'5" in length with a wide beam of 8'6" offering vast space to not only move around freely onboard but to also land the big catch of the day. Standard swim... View Details

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2026 Scout 240 Dorado

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Pewaukee, WI
- Pewaukee, WI
- Runabout
- 24'
- 2026 / New
- Call for price
Scout's 2026 240 Dorado showcases their NuV3 fuel efficient hull technology which effords you tremendous savings throughout your ownership. Loaded with family-friendly fishing feat... View Details

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2026 Scout 175 Sport Dorado

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Pewaukee, WI
- Pewaukee, WI
- Runabout
- 17'
- 2026 / New
- Call for price
Whether the day calls for a run out to your favorite fishing spot, tubing with the kids or just an evening cruise through the back country, the 175 Sport Dorado is up for the adven... View Details

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Showing 862 to 882 of 1,187 boats found.

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