Boats for sale in Chicago Illinois - BoatCrazy

747 boats found within 100 miles out of 11,741 Boats Found

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2026 Chaparral 21 SSi OB

$75,794

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 21'
- 2026 / New
- $75,794
Now on display, see this new 2026 Chaparral 21 SSi powered by a hearty 200 HP Yamaha 4-stroke outboard. Chaparral's innovative use of space means an abundance of cockpit space, sto... View Details

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$75,794
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2002 Regal 3860

$94,999

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 38'
- 2002 / Used
- $94,999
Stock #467673 Reason for selling is "New Adventure!". This Regal has now been on the market a couple months. Looking for any offers! Incredible luxury, performance, and a sound... View Details

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$94,999
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1999 Trojan 360 Express

$63,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 36'
- 1999 / Used
- $63,900
Spacious and Sporty, this Trojan (by Carver) 360 Express is the perfect family boat for cruising and enjoying the water! It is equipped with a Kohler generator for those hot summer... View Details

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$63,900
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2002 Maxum 2700 SCR

$29,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 28'
- 2002 / Used
- $29,900
This one-owner 2002 Maxum 2700 SCR has spent its life on the fresh waters of Southwest Michigan and shows the care you hope to find in a well-kept family cruiser. With sleek stylin... View Details

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$29,900
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2022 Robalo R242 Explorer

$108,900

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 24'
- 2022 / Used
- $108,900
This Freshwater only Robalo 242 Explorer is at the top of it's class and for good reason. This 24 foot platform is the pinnacle of what the Explorer series is all about. Providing... View Details

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$108,900
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2014 Chaparral 287 SSX

$69,600

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 28'
- 2014 / Used
- $69,600
Sharp, powerful Chaparral 287 SSX. Includes Volvo Penta 430 HP V-8 with DTS. Just 260 engine hours. Don’t miss out on this nicely maintained Chaparral 287 SSX. This 9-foot beam bo... View Details

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$69,600
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2004 Bayliner 245

$23,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 24'
- 2004 / Used
- $23,900
Bayliner's 245 Cruiser sports a comfortable cockpit and convenient cabin arrangement. The cockpit area includes a reversible portside companion seat -- converting from a forward fa... View Details

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$23,900
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2007 Sweetwater SW 1986 RE-3 Gate

$10,900

Saint Joseph, MI
- Saint Joseph, MI
- Pontoon
- 19'
- 2007 / Used
- $10,900
Trailer Included! See this 2007 Sweetwater SW 1986 RE-3 Gate, an affordable pontoon boat that combines comfort and functionality. With an overall length of approximately 19.17 fee... View Details

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$10,900
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1996 Monterey 276

$17,999

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 27'
- 1996 / Used
- $17,999
Stock #494642 This Monterey has now been on the market more than a month. Please submit your offer today! Updated seats and flooring in aft. The Monterey has a double bimini with... View Details

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$17,999
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1999 Sea Ray 290 Sundancer

$32,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 29'
- 1999 / Used
- $32,900
This 1999 Sea Ray 290 Sundancer is the perfect blend of weekend cruiser, sunset chaser, and floating cottage. Powered by twin mercury engines, this popular express cruiser offers t... View Details

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$32,900
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2016 Chaparral 257 SSX

$72,500

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 25'
- 2016 / Used
- $72,500
Boating's best 25-footer! Step onboard the sensational 257 SSX and experience the perfect mix of classic elegance and high tech innovation. Bow to stern, the eye appeal is simply s... View Details

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$72,500
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2026 Cobalt R8 Surf

$338,985

Fontana, WI
- Fontana, WI
- Ski & Wake
- 27'
- 2026 / New
- $338,985
At the heart of this R8 Surf is the Volvo V8-430CE forward-facing engine, delivering next-level performance with deep reserves of torque and precision control. Whether you’re build... View Details

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$338,985
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2026 Cobalt R8 Surf

$328,535

Fontana, WI
- Fontana, WI
- Ski & Wake
- 27'
- 2026 / New
- $328,535
From the moment you step aboard, the R8 Surf showcases the meticulous attention to detail that has made Cobalt one of the most respected names in boating. Rich wood interior accent... View Details

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$328,535
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2026 Malibu M230

$351,507

Fontana, WI
- Fontana, WI
- Ski & Wake
- 23'
- 2026 / New
- $351,507
Eye-catching Maya Blue exterior with a beautifully appointed Cool Sepia Brown and Maya Blue interior, this M230 delivers the perfect balance of luxury, innovation, and legendary Ma... View Details

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$351,507
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2000 Cobalt 190

$9,490

Fontana, WI
- Fontana, WI
- Bowrider
- 18'
- 2000 / Used
- $9,490
Powered by a dependable 260 HP Mercury V8 with just 580 hours, this well-maintained sport boat delivers the smooth ride, responsive performance, and premium fit and finish that hav... View Details

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$9,490
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2026 Malibu 23LSV

$247,184

Fontana, WI
- Fontana, WI
- Ski & Wake
- 23'
- 2026 / New
- $247,184
2026 Malibu 23 LSV is powered by the proven Malibu Monsoon M5Di 360HP engine and includes a matching custom trailer. Engineered to create championship-caliber waves, this 23 LSV c... View Details

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$247,184
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2026 Axis A200

$130,075

Fontana, WI
- Fontana, WI
- Ski & Wake
- 20'
- 2026 / New
- $130,075
Powered by the renowned Malibu Monsoon M5Di engine, the A200 provides responsive power, exceptional reliability, and the performance needed to create unforgettable days on the wate... View Details

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$130,075
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2026 Axis A245

$151,987

Fontana, WI
- Fontana, WI
- Ski & Wake
- 24'
- 2026 / New
- $151,987
Powered by the proven Malibu Monsoon M5Di engine, the A245 delivers exhilarating performance, responsive handling, and the confidence to spend more time making memories and less ti... View Details

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$151,987
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2026 Cobalt R8

$199,990

Fontana, WI
- Fontana, WI
- Bowrider
- 27'
- 2026 / Used
- $199,990
Finished in a stunning Knockout Red hull with Navy accents, this R8 commands attention at every dock. The upscale Caramel and Carbon interior, complemented by the Dark Driftwood In... View Details

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$199,990
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2026 Malibu 26LSV

$339,975

Fontana, WI
- Fontana, WI
- Ski & Wake
- 26'
- 2026 / New
- $339,975
Powered by the legendary Monsoon LT4 607HP supercharged engine and paired with a matching tandem-axle trailer, this flagship Malibu combines breathtaking performance, world-class s... View Details

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$339,975
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2022 Cobalt CS23 Surf

$74,990

Fontana, WI
- Fontana, WI
- Bowrider
- 23'
- 2022 / Used
- $74,990
Experience the perfect blend of luxury, versatility, and watersports performance with this exceptionally well-maintained 2022 Cobalt CS23 Surf. Powered by a Volvo Penta V8 300 HP e... View Details

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$74,990
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Showing 337 to 357 of 747 boats found.

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