Boats for sale in Chicago Illinois

1,705 boats found within 100 miles out of 15,158 Boats Found

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2002 Regal 3860

$109,000

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 38' / 0'
- 2002 / Used
- $109,000
Stock #467673 Reason for selling is "New Adventure!". This is a new advertisement, on the market just this week (May 1st). Always accepting offers! Incredible luxury, performanc... View Details

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$109,000
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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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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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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

$75,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 23' / 8'
- 2023 / Used
- $75,900
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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$75,900
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2001 Regal Commodore 2660

$36,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 29' / 8'
- 2001 / Used
- $36,900
Tandem Axle Trailer included! Twin Volvo V-6's. Luxurious, sporty and spacious, this Regal 2660 Commodore also features the option of trailering to your summer destinations! The co... View Details

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$36,900
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2026 Chaparral 23 SSi

$89,259

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 23' / 8'
- 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' / 8'
- 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' / 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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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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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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2003 Chaparral 260 SSi

$34,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 27' / 0'
- 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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2016 Chaparral 287 SSX

$74,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 28' / 0'
- 2016 / Used
- $74,900
See this sharp, spacious fun machine, ready to take you to your favorite destinations. This 9-foot beam bow rider offers an abundance of comfortable passenger seating with a double... View Details

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$74,900
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2018 Lund LX220 Pontoon

$39,900

Saint Joseph, MI
- Saint Joseph, MI
- Pontoon
- 23' / 0'
- 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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2002 Maxum 2700 SCR

$32,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 28' / 0'
- 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' / 0'
- 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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2011 Cobalt 302

$84,990

Fontana, WI
- Fontana, WI
- Bowrider
- 29' / 9'
- 2011 / Used
- $84,990
Powered by twin Mercury 350 MAG MPI Bravo III engines, the 302 delivers exhilarating performance, confident handling, and smooth acceleration whether you’re cruising with family, e... View Details

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$84,990
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2024 Cobalt 220S

$45,990

Fontana, WI
- Fontana, WI
- Bowrider
- 21' / 8'
- 2024 / Used
- $45,990
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$45,990
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2022 Malibu 20VTX

$134,772

Fontana, WI
- Fontana, WI
- Ski & Wake
- 20' / 98'
- 2022 / Used
- $134,772
The 20 VTX is Malibu's ultimate triple threat. VTX stands for versatility and it truly is the boat that makes everyone happy whether you want to ski, wakesurf, or wakeboard. Its un... View Details

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$134,772
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2026 Cobalt R8 Surf

$310,123

Fontana, WI
- Fontana, WI
- Ski & Wake
- 27' / 8'
- 2026 / New
- $310,123
At its core is the upgraded Volvo V8-380CE forward-facing engine, delivering exhilarating performance with the smooth, confident handling Cobalt is known for. Whether you’re dialin... View Details

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$310,123
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2026 Cobalt R8 Surf

$338,985

Fontana, WI
- Fontana, WI
- Ski & Wake
- 27' / 8'
- 2026 / New
- $338,985
At the heart of this R8 Surf is the Volvo V8-430CE forward-facing engine, delivering next-level performance with deep reserves of torque and precision control. Whether you’re build... View Details

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$338,985
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