Boats for sale in Chicago Illinois - BoatCrazy

1,208 boats found within 100 miles out of 14,706 Boats Found

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2025 Robalo R202 Explorer

$83,728

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 20' / 8'
- 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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2025 Robalo R160 Center Console

$41,430

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 16' / 7'
- 2025 / New
- $41,430
The R160 makes every on-water adventure more fun in a size that's easy to trailer and store. But don't think that it isn't designed with performance in-mind. Featuring the same on-... View Details

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$41,430
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2025 Chaparral 307 SSX

Call for price

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 30' / 9'
- 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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2004 Bayliner 245

$23,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 24' / 8'
- 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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2006 Chaparral 310 Signature

$64,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 31' / 10'
- 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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1995 Sea Ray 400 Express Cruiser

$62,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 40' / 13'
- 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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2005 Formula 260 Bowrider

$46,900

Saint Joseph, MI
- Saint Joseph, MI
- Runabout
- 26' / 8'
- 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

$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

$134,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 30' / 9'
- 2016 / Used
- $134,900
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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$134,900
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2000 Chaparral Signature 300

$37,500

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 29' / 10'
- 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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2025 Cobalt R6

$189,990

Fontana, WI
- Fontana, WI
- Bowrider
- 25' / 8'
- 2025 / Used
- $189,990
This almost new 2025 Cobalt R6, a perfect blend of striking design, luxury appointments, and exhilarating performance. Powered by the Volvo V8-380CE DP, this R6 delivers smooth, re... View Details

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$189,990
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2024 Cobalt R4

$119,990

Fontana, WI
- Fontana, WI
- Bowrider
- 24' / 8'
- 2024 / Used
- $119,990
2024 Cobalt R4. Adorned in a striking Navy & Cabernet exterior, complemented by a luxurious Carmel & Carbo interior, this vessel is the epitome of sophistication on the water. Powe... View Details

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$119,990
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2022 Cobalt R8 Surf

$197,900

Fontana, WI
- Fontana, WI
- Ski & Wake
- 27' / 8'
- 2022 / Used
- $197,900
Experience luxury, performance, and surf-ready innovation with this exceptionally maintained 2022 Cobalt R8 Surf — showing just 70 hours of freshwater use. Combining Cobalt’s renow... View Details

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$197,900
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2026 Cobalt R31 Surf

$585,211

Fontana, WI
- Fontana, WI
- Ski & Wake
- 31' / 10'
- 2026 / New
- $585,211
This R31 Surf is equipped with twin Volvo 380hp forward-facing engines with joystick control, giving you effortless handling, pinpoint docking, and exhilarating acceleration at you... View Details

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$585,211
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2013 Malibu 23 LSV

$47,990

Fontana, WI
- Fontana, WI
- Ski & Wake
- 23' / 102'
- 2013 / Used
- $47,990
If you’ve been looking for the perfect mix of size, style, and surf performance, look no further than this 2013 Malibu 23LSV. As Malibu’s flagship wake boat, the 23LSV set the stan... View Details

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$47,990
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1997 Sea Ray 210

$6,000

Fontana, WI
- Fontana, WI
- Bowrider
- 21' / 8'
- 1997 / Used
- $6,000
Classic style meets trusted performance with this 1997 Sea Ray 210, a versatile bowrider that’s perfect for family cruising, watersports, and long days on the lake. Well-built and... View Details

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$6,000
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2024 Cobalt R8 Surf

$249,990

Fontana, WI
- Fontana, WI
- Ski & Wake
- 27' / 8'
- 2024 / Used
- $249,990
Experience the ultimate in wake and surf performance with this 2024 Cobalt R8 Surf, powered by a forward-facing 380hp Volvo engine. With only 19 hours, this boat is practically new... View Details

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$249,990
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