Boats for sale in Chicago Illinois

1,633 boats found within 100 miles out of 14,358 Boats Found

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2025 Chaparral 307 SSX

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Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 30'
- 2025 / New
- Call for price
Now in stock! Step aboard one of Chaparral's most innovative designs - the spacious, sleek and powerful 307 SSX. With an abundance of comfortably contoured cockpit seating, lot of... View Details

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1995 Sea Ray 400 Express Cruiser

$62,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 40'
- 1995 / Used
- $62,900
Nicely maintained fresh-water Sea Ray 400 Express. Twin Merc 454's with 537 engine hours, original. This classic express cruiser helped usher in the new era mid-'90's Sea Ray desig... View Details

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$62,900
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2019 Formula 350 Crossover Bowrider

$325,000

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 35'
- 2019 / Used
- $325,000
See this Gorgeous fresh-water Formula 350 CBR with just 140 engine hours! Recent price reduction. Ready to go boating now. The 350 CBR offers an ideal combination of luxurious cock... View Details

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$325,000
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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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2025 Chaparral 23 SSi

$96,864

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 23'
- 2025 / New
- $96,864
In Stock Now See the Chaparral 23 SSi, our best-selling 23-footer! This 23 SSi is superbly equipped with Mercury 300 HP Bravo 3 MPI power and many Chaparral extras. Trailer include... View Details

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$96,864
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2026 Chaparral 23 SSi

$89,259

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 23'
- 2026 / New
- $89,259
Everything that has made Chaparral's wildly popular SSi Series the talk of the waterways, gets bigger and better with the amazing 23 SSi. With a ChaparralONE price including the tr... View Details

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$89,259
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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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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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2026 Chaparral SSX 6

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Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 26'
- 2026 / New
- Call for price
Look no further-the SSX 6 is breaking barriers and setting the standard for on-water comfort and performance. Equipped with a state-of-the-art oversized touchscreen display, the he... View Details

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2017 Chaparral 21 H2O Ski & Fish

$34,900

Saint Joseph, MI
- Saint Joseph, MI
- Fish & Ski
- 21'
- 2017 / Used
- $34,900
Sold new @ Pier 33 in 2017 this boat has lived on its factory trailer and has been garaged since its purchase! With very low freshwater only hours on the motor this little runabout... View Details

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$34,900
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2018 Lund LX220 Pontoon

$39,900

Saint Joseph, MI
- Saint Joseph, MI
- Pontoon
- 23'
- 2018 / Used
- $39,900
Meet your ticket to endless summer fun on this 2018 Lund LX220 Tritoon. This Lund brings the perfect blend of power, comfort, and pure on-the-water fun. Powered by a 200HP Mercury... View Details

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$39,900
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2017 Regal 2500 Bowrider

$69,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 26'
- 2017 / Used
- $69,900
This 2017 Regal 2500 Bowrider is the kind of boat that makes people suddenly volunteer to bring the snacks. Sleek, sporty, and loaded with Regal style and ready for her next captai... View Details

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$69,900
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2003 Chaparral 260 SSi

$34,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 27'
- 2003 / Used
- $34,900
In our showroom now! If you are looking for a great value in today's boating market this is it! This lovingly cared for 260 SSi has only 543 freshwater hours on the Mercruiser 496... View Details

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$34,900
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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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2023 Custom Built 25 Hadlee Houseboat

$69,000

South Haven, MI
- South Haven, MI
- Houseboat
- 25'
- 2023 / Used
- $69,000
Custom Built Houseboat Immerse yourself in stylish and comfortable houseboat living with this newly built 2023 Hadley Houseboat, only the third one built, the other two have b... View Details

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$69,000
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2026 Mastercraft X24

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Pewaukee, WI
- Pewaukee, WI
- 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 Yamaha SX195

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Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha SX195, built to elevate your weekends. Experience unrivaled supercharged performance, striking styling, and exceptional value in its class. Key Features... View Details

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2025 Harris 230 Cruiser

$69,523

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2025 / New
- $69,523
Contact us to find out ALL available savings! Luxurious Adventures Await with the 2025 Harris 230 Cruiser Embark on opulent escapades aboard the prestigious 2025 Harris 230 Cruiser... View Details

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$69,523
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2026 Yamaha 222S

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Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 22'
- 2026 / New
- Call for price
The 2026 Yamaha 222S, timeless style, premium performance. The 222S combines timeless styling, premium refinements, and class-leading performance in an affordable 22-foot package.... View Details

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