Boats for sale in Chicago Illinois

1,585 boats found within 100 miles out of 14,269 Boats Found

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2007 Chaparral 350 Signature

$129,500

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 37'
- 2007 / Used
- $129,500
Always fresh-water, loaded with features. Twin Merc 8.1L 370 HP inboards with 460 hours. This is an ideal opportunity to own a well-cared-for Chaparral 350 Signature featuring a pr... View Details

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$129,500
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2005 Formula 260 Bowrider

$46,900

Saint Joseph, MI
- Saint Joseph, MI
- Runabout
- 26'
- 2005 / Used
- $46,900
Chase sunsets with this 2005 Formula 260 Bowrider, a premium sport boat built for performance, comfort, and luxury. A top brand known for its superior handling, quality constructio... View Details

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$46,900
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2018 Chaparral Vortex 203 VRX

$32,900

Saint Joseph, MI
- Saint Joseph, MI
- Jet boat
- 20'
- 2018 / Used
- $32,900
The 203 VRX features the hull design, interior layout and high quality construction Chaparral is known for. In addition to the head-turning style, the VRX includes a black folding... View Details

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$32,900
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2000 Crownline 290 CR

$34,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 31'
- 2000 / Used
- $34,900
This Crownline 290 CR is a spacious small express cruiser powered by twin Mercruiser 5.7 EFI's and NEW Bravo III drives! She has about 700 hours on her hour meters and appears to h... View Details

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$34,900
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2021 Qwest LS 822 DS Bar

$49,900

Saint Joseph, MI
- Saint Joseph, MI
- Pontoon
- 22'
- 2021 / Used
- $49,900
This 2021 Qwest LS 822 perfectly blends style and performance with great fishing capabilites. Power by a 200HP Honda and Upgraded tiple toon package and aluminum underskining makes... View Details

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$49,900
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2017 Chaparral 330 Signature

$194,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 33'
- 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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2016 Chaparral 307 SSX

$129,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 30'
- 2016 / Used
- $129,900
Meet your next on-the-water obsession: the 2016 Chaparral 307 SSX a head turning mix of luxury, performance, and pure boating bliss! At 30 feet, she delivers a ride as smooth as s... View Details

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$129,900
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2000 Chaparral Signature 300

$37,500

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 29'
- 2000 / Used
- $37,500
If you are looking for a small family cruiser with all the amenities you just found it! This Chaparral Signature 300 has all the creature comforts including Air Conditioning, Fusio... View Details

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$37,500
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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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2002 Regal 3860

$109,000

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 38'
- 2002 / Used
- $109,000
Stock #467673 Reason for selling is "New Adventure!". This Regal has recently been added to market (May 1st). Submit your offer today! Incredible luxury, performance, and a soun... View Details

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$109,000
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1999 Trojan 360 Express

$68,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 36'
- 1999 / Used
- $68,900
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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$68,900
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2002 Maxum 2700 SCR

$32,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 28'
- 2002 / Used
- $32,900
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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$32,900
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2006 Chaparral 310 Signature

$64,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 31'
- 2006 / Used
- $64,900
This 2006 Chaparral 310 Signature is a sleek and luxurious cruiser designed for thosewho appreciate both performance and comfort on the water. With a length overall of 33 feet and... View Details

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$64,900
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2022 Robalo R242 Explorer

$119,900

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 24'
- 2022 / Used
- $119,900
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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$119,900
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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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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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