Boats for sale in Chicago Illinois

1,169 boats found within 100 miles out of 14,859 Boats Found

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2018 Chaparral Vortex 203 VRX

$35,900

Saint Joseph, MI
- Saint Joseph, MI
- Jet boat
- 20' / 8'
- 2018 / Used
- $35,900
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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$35,900
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2000 Crownline 290 CR

$34,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 31' / 10'
- 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' / 8'
- 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' / 10'
- 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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2018 Chaparral 191 Suncoast

$37,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 20' / 8'
- 2018 / Used
- $37,900
The 191 Suncoast breaks down boating to its basics, while not sacrificing the Chaparral design, style, and quality you have come to expect. A large open concept seating arrangement... View Details

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$37,900
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2016 Chaparral 307 SSX

$138,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 30' / 9'
- 2016 / Used
- $138,900
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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$138,900
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2000 Chaparral Signature 300

$39,000

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 29' / 10'
- 2000 / Used
- $39,000
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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$39,000
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2026 Chaparral SSX 4

Call for price

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 24' / 8'
- 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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2003 Chaparral 260 SSi

$34,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 27' / 0'
- 2003 / Used
- $34,900
Arriving at Pier 33 soon! 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... View Details

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$34,900
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2019 Chaparral 21 H2O Sport

$36,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 21' / 0'
- 2019 / Used
- $36,900
With only 98 hours on it this 21' H2O Sport has had a cushy freshwater life on Lake Michigan and has always been rack stored indoors since new. She performs like a BMW 3 Series on... View Details

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$36,900
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2017 Chaparral 21 H2O Ski & Fish

$34,900

Saint Joseph, MI
- Saint Joseph, MI
- Fish & Ski
- 21' / 8'
- 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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2026 Chaparral 21 SSi

$73,189

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 21' / 8'
- 2026 / New
- $73,189
See this New 2026 Chaparral 21 SSi! How much fun can you pack into one summer? Plenty, aboard your new Chaparral. Trailerable to your favorite destinations. Nimble, efficient and p... View Details

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$73,189
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2024 Chaparral 267 SSX

$140,000

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 26' / 0'
- 2024 / Used
- $140,000
Currently Inside Heated Storage, More Pictures To Come In Spring! The Chaparral 267 SSX is breaking barriers and setting the standard in quality. Equipped with state of the art du... View Details

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$140,000
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2026 Chaparral SSX 6

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Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 26' / 8'
- 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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2019 Formula 350 Crossover Bowrider

$325,000

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 35' / 10'
- 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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2018 Chaparral Vortex 223 VRX

$47,700

Saint Joseph, MI
- Saint Joseph, MI
- Jet boat
- 22' / 8'
- 2018 / Used
- $47,700
Chaparral put all the knowledge we've learned about boat building in the last 50 years into the 223 VRX. The end result is a family jet boat that's priced right, built right and ex... View Details

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$47,700
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2007 Cobalt 323

$89,900

Saint Joseph, MI
- Saint Joseph, MI
- Runabout
- 32' / 10'
- 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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2007 Yamaha SX230

$24,900

Saint Joseph, MI
- Saint Joseph, MI
- Jet boat
- 23' / 8'
- 2007 / Used
- $24,900
This sweet Yamaha SX 230 with twin 140 hp jet drives is guaranteed fun for the family! Ski, tube, and cruise in the river or on the Big Lake with your friends and family! This boat... View Details

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$24,900
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2025 Chaparral 23 SSi

$96,864

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 23' / 8'
- 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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2023 Chaparral 23 SSi

$79,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 23' / 8'
- 2023 / Used
- $79,900
Summer isn't over yet with this 2023 Chaparral 23 SSI ! Fully loaded and ready to go, this like new Chaparral comes with a professionally installed Rockford Fosgate sound system th... View Details

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$79,900
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2017 Chaparral 257 SSX

$79,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 25' / 8'
- 2017 / Used
- $79,900
Step onboard the sensational 257 SSX and experience the perfect mix of performance, styling, comfort and fun! You will enjoy Great performance from Mercury's 6.2L 350 HP with Bravo... View Details

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$79,900
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