Boats for sale in Chicago Illinois - BoatCrazy

733 boats found within 100 miles out of 11,627 Boats Found

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2026 Harris Cruiser 210

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Walworth, WI
- Walworth, WI
- Pontoon
- 22'
- 2026 / New
- Call for price
Introducing the 2026 Harris Cruiser 210, built without compromise. Invite your friends waterskiing, take the kids for a sun-soaked day of cruising, or escape alone and cast a line.... View Details

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2026 Harris Cruiser 230

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Walworth, WI
- Walworth, WI
- Pontoon
- 23'
- 2026 / New
- Call for price
Introducing the 2026 Harris Cruiser 230, built without compromise. Invite your friends waterskiing, take the kids for a sun-soaked day of cruising, or escape alone and cast a line.... View Details

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2026 Sea Ray SPX 210

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Walworth, WI
- Walworth, WI
- Runabout
- 21'
- 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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2026 Harris Sunliner 230 Sport

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Walworth, WI
- Walworth, WI
- Pontoon
- 23'
- 2026 / New
- Call for price
Introducing the 2026 Harris Sunliner 230 Sport, crafted for adventure. With flexible seating arrangements and easy style, Sunliner is the pontoon built to fit your family. Make a s... View Details

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2026 Harris Solstice 250

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Walworth, WI
- Walworth, WI
- Pontoon
- 26'
- 2026 / New
- Call for price
Pursue adventure with the 2026 Harris Solistice 250. Reimagined and ready for action, the Solstice has more power, more luxury comfort and more standard features than ever before.... View Details

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2026 Harris Sunliner 250

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Walworth, WI
- Walworth, WI
- Pontoon
- 26'
- 2026 / New
- Call for price
Introducing the 2026 Harris Sunliner 250, crafted for adventure. With flexible seating arrangements and easy style, Sunliner is the pontoon built to fit your family. Make a splash.... View Details

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2026 Harris Sunliner 230

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Walworth, WI
- Walworth, WI
- Pontoon
- 23'
- 2026 / New
- Call for price
Introducing the 2026 Harris Sunliner 230, crafted for adventure. With flexible seating arrangements and easy style, Sunliner is the pontoon built to fit your family. Make a splash.... View Details

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2026 Harris Sunliner 210

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Walworth, WI
- Walworth, WI
- Pontoon
- 22'
- 2026 / New
- Call for price
Introducing the 2026 Harris Sunliner 210, crafted for adventure. With flexible seating arrangements and easy style, Sunliner is the pontoon built to fit your family. Make a splash.... View Details

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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 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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Showing 442 to 462 of 733 boats found.

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