Boats for sale in Chicago Illinois - BoatCrazy

1,734 boats found within 100 miles from Chicago, Illinois

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2025 Mastercraft XT23

$184,295

Antioch, IL
- Antioch, IL
- Ski & Wake
- 23' / 0'
- 2025 / New
- $184,295
Contact us to find out ALL available savings! Thanks to a unique hull design paired with MasterCraft's integrated SurfStar system, the XT23 leads the industry in the performance of... View Details

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$184,295
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2026 Malibu 21LX

$184,885

Fontana, WI
- Fontana, WI
- Ski & Wake
- 21' / 98'
- 2026 / New
- $184,885
Step aboard the 2026 Malibu 21LX, a precision-engineered wake boat that transforms every outing into a full-throttle lifestyle experience. Powered by the robust Monsoon M5Di engine... View Details

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$184,885
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2026 Robalo Center Console R270

$185,755

Racine, WI
- Racine, WI
- Fishing Center Console
- 27' / 9'
- 2026 / New
- $185,755
Introducing the sleek and stylish 2026 Robalo Center Console R270 New Boat, available in a stunning array of colors including Alloy Gray, Biscayne Blue, Ice Blue, Atlas Blue, Shark... View Details

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$185,755
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2026 Malibu 21LX

$186,282

Fontana, WI
- Fontana, WI
- Ski & Wake
- 21' / 98'
- 2026 / New
- $186,282
Turn every summer into a highlight reel with this 2026 Malibu 21 LX, finished in a clean, modern Arctic White & Vapor Blue exterior that looks incredible on the dock and even bette... View Details

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$186,282
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2024 Robalo R250 Center Console

$186,446

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 25' / 9'
- 2024 / New
- $186,446
On Display Now, see this superbly equipped Robalo R250 Center Console. Featuring Robalo's latest design elements, the R250 is truly a big-water boat, with a nine-foot two-inch beam... View Details

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$186,446
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2022 Cobalt R8 Surf

$188,990

Fontana, WI
- Fontana, WI
- Ski & Wake
- 27' / 8'
- 2022 / Used
- $188,990
Experience luxury, performance, and surf-ready innovation with this exceptionally maintained 2022 Cobalt R8 Surf — showing just 70 hours of freshwater use. Combining Cobalt’s renow... View Details

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$188,990
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2024 Cobalt R8

$189,990

Fontana, WI
- Fontana, WI
- Bowrider
- 27' / 8'
- 2024 / Used
- $189,990
Powered by a commanding Volvo V8 380hp engine, this beauty propels you across the water with breathtaking speed and unmatched performance. The dual props provide precise control an... View Details

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$189,990
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2024 Mastercraft XT25

$189,995

Antioch, IL
- Antioch, IL
- Ski & Wake
- 25' / 0'
- 2024 / New
- $189,995
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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$189,995
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2025 Robalo R250

$193,625

Racine, WI
- Racine, WI
- Performance
- 25' / 9'
- 2025 / New
- $193,625
2025 Robalo R250 Twin Mercury DTS 200XL Standard Factory Options Included With this Package: - Solid Hull Alloy Gray Gel Coat - Cockpit Interior - Harbor Gray - Hard Top Complet... View Details

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$193,625
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2017 Chaparral 330 Signature

$194,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 33' / 10'
- 2017 / Used
- $194,900
Now available, see this 2017 Chaparral 330 Signature. Always fresh-water, with just 243 engine hours. Designed for summer adventures and weekend getaways, the Chaparral 330 Signatu... View Details

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$194,900
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2024 Sea Ray SLX 260 Surf

$196,370

Walworth, WI
- Walworth, WI
- Bowrider
- 26' / 0'
- 2024 / New
- $196,370
Contact us to find out ALL available savings! All Sale and/or Clearance Prices include all rebates and incentives.Discover a carefree escape from the ordinary in a boat that shines... View Details

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$196,370
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2026 Robalo Dual Console R277

$196,655

Racine, WI
- Racine, WI
- Performance
- 27' / 9'
- 2026 / New
- $196,655
Introducing the sleek and stylish 2026 Robalo Dual Console R277, available in a stunning finish that will turn heads out on the water. This bowrider is a true showstopper with its... View Details

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$196,655
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2025 Sea Ray SDX 270 Outboard

$197,794

Antioch, IL
- Antioch, IL
- Runabout
- 27' / 0'
- 2025 / New
- $197,794
Act fast on this limited-time offer! 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 heig... View Details

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$197,794
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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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2005 Regal COMMODORE 4260

$199,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 45' / 0'
- 2005 / Used
- $199,900
Regal's beloved 4260 Commodore! The lay out was one of Regal's best, and package with this boat with rebuilt Yanmars with less than 250 hours since rebuild, it will be perfect for... View Details

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$199,900
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2024 Mastercraft X24

$204,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 24' / 9'
- 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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2026 Cobalt R6

$210,242

Fontana, WI
- Fontana, WI
- Bowrider
- 25' / 8'
- 2026 / New
- $210,242
The perfect balance of luxury and performance, finished in a stunning Deep Teal exterior paired with a rich Summit/Cocoa interior that feels both modern and timeless. It’s the kind... View Details

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$210,242
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2026 Robalo R257

$211,250

Racine, WI
- Racine, WI
- Performance
- 25' / 9'
- 2026 / New
- $211,250
2026 Robalo R257 - Dual Console - White Twin Yamaha Four Stroke F200XSA2 White - with Electro Hydraulic Steering Coyote Aluminum Tandem Axle Trailer Standard Factory Options Inc... View Details

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$211,250
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2026 Cobalt R6

$217,843

Fontana, WI
- Fontana, WI
- Bowrider
- 25' / 8'
- 2026 / New
- $217,843
The R6 delivers the perfect balance of space, agility, and sophistication, making it one of the most versatile premium bowriders on the water.Finished in an eye-catching Glacier Bl... View Details

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$217,843
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1990 Jefferson Marquessa 52

$219,900

Saint Joseph, MI
- Saint Joseph, MI
- Yacht
- 52' / 16'
- 1990 / Used
- $219,900
Classically-designed fresh-water motoryacht, now available! Three staterooms, three heads, split walk-in engine rooms, plus comfortable luxury in every direction. Gorgeous teak woo... View Details

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$219,900
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2024 Cobalt R8 Outboard

$219,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 27' / 8'
- 2024 / Used
- $219,900
See This stunning 2024 Cobalt R8 Outboard, a remarkable bowrider that combines elegance with performance. Measuring an impressive 27.83 feet in overall length, this vessel is craft... View Details

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$219,900
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Showing 799 to 819 of 1,734 boats found.

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