Boats for sale in Chicago Illinois

787 boats found within 100 miles out of 11,638 Boats Found

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2026 Mastercraft X24

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Antioch, IL
- Antioch, IL
- Ski & Wake
- 24'
- 2026 / New
- Call for price
The Mastercraft X24: Experience the epitome of adrenaline-fueled excitement and aquatic thrills with the Mastercraft X24. A powerhouse vessel designed to create unforgettable momen... View Details

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2026 Sea Ray SDX 290

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Antioch, IL
- Antioch, IL
- 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 SPX 210 Outboard

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Antioch, IL
- Antioch, IL
- Runabout
- 24'
- 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 SDX 270 Outboard

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Antioch, IL
- Antioch, IL
- 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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2005 Cruisers 300 Express

$48,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 31'
- 2005 / Used
- $48,900
EXCEPTIONAL OPPORTUNITYJUST 79 FRESHWATER HOURS! TWIN MERC 5.0 MPI BRAVO III'S MANY EXTRAS ... NEAR-TO-NEW CONDITION There are few opportunities to obtain this type of savings on a... View Details

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$48,900
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2002 Regal 2450 LSC

$24,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 23'
- 2002 / Used
- $24,900
The sleek, modern design silhouette of the Regal 2450 LSC brilliantly disguises a most generous cuddy cabin with 5 feet, 6 inches of sitting headroom. Wraparound cockpit seating in... View Details

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$24,900
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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

$31,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 29'
- 1999 / Used
- $31,900
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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$31,900
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2016 Chaparral 257 SSX

$69,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 25'
- 2016 / Used
- $69,900
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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$69,900
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2026 Chaparral SSX 4

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Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 24'
- 2026 / New
- Call for price
The SSX 4 packs more elegance, performance, and innovation than boaters have ever experienced at this widely popular length. Its stylish lines, meticulous attention to detail, and... View Details

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2023 Robalo R272 Center Console

$179,900

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 27'
- 2023 / Used
- $179,900
Whether you're trolling with hooks in the water or running through rough seas in search of a trophy catch, Robalo's R272 center console sparks an adrenaline rush unlike any other f... View Details

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$179,900
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2007 Cobalt 323

$89,900

Saint Joseph, MI
- Saint Joseph, MI
- Runabout
- 32'
- 2007 / Used
- $89,900
If you're in search of the perfect combination of luxury, performance, and offshore capabilities, look no further than this 2007 Cobalt 323. Cobalt is known for its sleek design an... View Details

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$89,900
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2024 Robalo R250 Center Console

$176,446

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 25'
- 2024 / New
- $176,446
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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$176,446
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2006 Formula 330 Sun Sport

$94,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 33'
- 2006 / Used
- $94,900
If you are looking for a sporty, great performing, hot looking express cruiser, look no further! This Formula 330 Sun Sport is the perfect fit for your family's summer fun! Nicely... View Details

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$94,900
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2024 Robalo R180 Center Console

$66,244

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 18'
- 2024 / New
- $66,244
On Display Now, see this Robalo R180 Center Console -- Loaded with our favorite factory options! Packed with features, durable quality and paired with Yamaha dependability. Enjoy... View Details

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$66,244
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2025 Robalo R202 Explorer

$83,728

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 20'
- 2025 / New
- $83,728
Robalo's R202 Explorer offers the convenience of a center console layout and ease of maintenance, plus expanded seating comfort for a full day of on-water family fun. Well-padded f... View Details

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$83,728
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1996 Cruisers 3375 Rogue

$40,000

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 33'
- 1996 / Used
- $40,000
Stock #457168 Reason for selling is "Bought another boat". ANY and ALL offers will be put in front of our seller! Submit your offer today! Two Berths, Ready to Show, Slip and St... View Details

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$40,000
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