Boats for sale in Chicago Illinois

1,753 boats found within 100 miles out of 15,391 Boats Found

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1996 Caliber 1 35 LRC

$85,000

Racine, WI
- Racine, WI
- Sailboat
- 35' / 11'
- 1996 / Used
- $85,000
1996 Caliber 35 LRC "Archangel" This is a single owner vessel, purchased new in '96 and used exclusivley for cruising Lake Michigan. The boat has been really well cared for as wa... View Details

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$85,000
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2026 Dufour 37

$369,000

Racine, WI
- Racine, WI
- Sailboat
- 0' / 12'
- 2026 / New
- $369,000
2026 Dufour 37 This 2026 Dufour 37 is a rare opportunity to acquire a turnkey, revenue-producing sailboat with established demand, full utilization, and professional management al... View Details

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$369,000
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2026 Robalo R317 Dual Console

$361,870

Racine, WI
- Racine, WI
- Performance
- 0' / 0'
- 2026 / New
- $361,870
On Order, Expected June 2026!! 2026 Robalo R317 Twin Yamaha F350USA2 4.3L V6 - White Hull - Yamaha Helm Master EX with Maneuverability - Cockpit Interior - Harbor Black - Canvas... View Details

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$361,870
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2001 Regal 1900 LSR

$9,000

Racine, WI
- Racine, WI
- Performance
- 18' / 8'
- 2001 / Used
- $9,000
New Listing! Vessel Available! 2001 Regal 1900 LSR Powered by the Volvo Penta 4.3 GL Bimini Top Cockpit and bow storage cover Single axle trailer Misc. life jackets included... View Details

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$9,000
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2007 Hunter 38

$109,000

Racine, WI
- Racine, WI
- Sailboat
- 0' / 12'
- 2007 / Used
- $109,000
2007 Hunter 38 Available for viewing!! Overview If you’ve been waiting for the right cruising sailboat—this is it. This 2007 Hunter 38 delivers the perfect combination of perfo... View Details

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$109,000
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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

$99,990

Fontana, WI
- Fontana, WI
- Ski & Wake
- 20' / 98'
- 2022 / Used
- $99,990
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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$99,990
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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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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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2023 Malibu 25 LSV

$160,390

Fontana, WI
- Fontana, WI
- Ski & Wake
- 25' / 8'
- 2023 / Used
- $160,390
2023 Malibu 25 LSV, the ultimate luxury wakeboarding and surfing machine. This stunning boat is equipped with a powerful M6Di engine, producing a whopping 430 horsepower, making it... View Details

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$160,390
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2026 Malibu 21LX

$184,885

Fontana, WI
- Fontana, WI
- Ski & Wake
- 21' / 98'
- 2026 / New
- $184,885
Step aboard the 2026 Malibu 21LX, a precision-engineered wake boat that transforms every outing into a full-throttle lifestyle experience. Powered by the robust Monsoon M5Di engine... View Details

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$184,885
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2026 Malibu 21LX

$186,282

Fontana, WI
- Fontana, WI
- Ski & Wake
- 21' / 98'
- 2026 / New
- $186,282
Turn every summer into a highlight reel with this 2026 Malibu 21 LX, finished in a clean, modern Arctic White & Vapor Blue exterior that looks incredible on the dock and even bette... View Details

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$186,282
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2026 Malibu 22LSV

$222,898

Fontana, WI
- Fontana, WI
- Ski & Wake
- 21' / 102'
- 2026 / New
- $222,898
Finished in a bold Ebony and Arctic White exterior with refined Wakesetter graphics, this 22LSV delivers unmistakable presence from every angle. Step onboard and you’re welcomed by... View Details

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$222,898
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2012 Malibu Wakesetter 22 MXZ

$49,990

Fontana, WI
- Fontana, WI
- Bowrider
- 22' / 8'
- 2012 / Used
- $49,990
Make every day on the water unforgettable with this 2012 Malibu 22 MXZ, a legendary wake machine built for those who crave performance, comfort, and cutting-edge style. Designed wi... View Details

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$49,990
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2008 Sea Ray 240 SunDeck

$22,990

Fontana, WI
- Fontana, WI
- Bowrider
- 26' / 8'
- 2008 / Used
- $22,990
2008 Sea Ray 240 Sundeck – Spacious, Stylish, and Built for Fun Enjoy the best days on the water aboard this 2008 Sea Ray 240 Sundeck—a perfect blend of sporty performance and fam... View Details

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$22,990
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2023 Malibu 24 MXZ

$159,990

Fontana, WI
- Fontana, WI
- Ski & Wake
- 24' / 8'
- 2023 / Used
- $159,990
Powered by the M6Di Monsoon engine, this 24MXZ delivers massive torque, smooth acceleration, & the muscle needed to build world-class waves. Equipped with Surf Gate & the Malibu Su... View Details

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$159,990
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2023 ATX Surf Boats ATX Surf Boats 20 Type-S

$74,990

Fontana, WI
- Fontana, WI
- Ski & Wake
- 20' / 102'
- 2023 / Used
- $74,990
Get ready to elevate your summer with this ATX Type-S 20’, a sleek, powerful surf and wake machine that delivers performance, style, and fun in one incredible package. With only 88... View Details

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$74,990
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