Boats for sale in Chicago Illinois - BoatCrazy

1,680 boats found within 100 miles out of 15,245 Boats Found

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2026 Mastercraft ProStar

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Ski & Wake
- 20' / 0'
- 2026 / New
- Call for price
The 2026 MasterCraft Prostar is a purpose-obsession wakeski boat-refined for today's skiers and ready for the next generation. With perfected ergonomics, a meticulously designed hu... View Details

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2026 Mastercraft XT23

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Ski & Wake
- 23' / 0'
- 2026 / New
- Call for price
Introducing the 2026 MasterCraft XT23. With head-turning looks, serious wave-making power, and comfort to keep everyone happy, the XT23 is built to take over the lake-not just hand... View Details

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2026 Yamaha 222 FSH Sport

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 22' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha 222 FSH Sport, the perfect catch. The 222 FSH Sport redefines excellence in 22-foot center console boats with its powerful twin-engine setup, offering s... View Details

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2026 Yamaha 220 FSH Sport

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 22' / 0'
- 2026 / New
- Call for price
Fish to wake on the 2026 Yamaha 220 FSH Sport. Enjoy the perfect blend of versatility and affordability with the 220 FSH Sport. Whether you're wakesurfinhg, fishing, cruising or en... View Details

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2026 Mastercraft NXT23

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Ski & Wake
- 23' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Mastercraft NXT23. Built to keep things simple-without sacrificing an ounce of performance. With SurfStar and ample ballast, the NXT23 delivers clean, consiste... View Details

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2026 Yamaha 195 FSH Sport

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 19' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha 195 FSH Sport, style and performance at an affordable price. With it's sleek t-top design, powerful supercharged engine, innovative fishing features, an... View Details

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2026 Yamaha 255XD

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha 255XD, the ultimate jet-powered wakesurfer. The 255XD, with its combined 500 horsepower, features cutting-edge DRiVE X technology, exceptional wakesurf... View Details

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2026 Yamaha 190 FSH Sport

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 19' / 0'
- 2026 / New
- Call for price
Yamaha's most affordable center console boat, the 2026 Yamaha 190 FSH Sport. Enjoy all your favorite features combined in one, making this the most budget-friendly center console b... View Details

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2026 Yamaha 255XE

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25' / 0'
- 2026 / New
- Call for price
Unleashed power, wake technology, and style-all decribe the 2026 Yamaha 255XE. The 255XE, with a combined 500 horsepower, showcases advanced technology for exceptional wakesurf per... View Details

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2026 Mastercraft X24

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Ski & Wake
- 24' / 0'
- 2026 / New
- Call for price
The Mastercraft X24: Experience the epitome of adrenaline-fueled excitement and aquatic thrills with the Mastercraft X24. A powerhouse vessel designed to create unforgettable momen... View Details

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2026 Mastercraft XT20

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Ski & Wake
- 20' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Mastercraft XT20. At 20 feet, the XT20 is compact and garage-friendly-but still delivers everything you'd expect from a MasterCraft: SurfStar performance, prem... View Details

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2026 Yamaha 252XE

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha 252XE, made with superior design meets function. The 252XE, with its combined 400 horsepower, seamlessly integrates top watersports features with advanc... View Details

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2026 Sea Ray Sundancer 320

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 33' / 0'
- 2026 / New
- Call for price
Luxurious and practical, introducing the 2026 Sea Ray Sundancer 320. Experience the difference that comes from design that's equal parts luxurious and practical. From the spacious... View Details

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2016 Cruisers 380 EXPRESS

$279,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 38' / 0'
- 2016 / Used
- $279,900
Just listed: Fresh water since new, low hours (under 320!), Axius joystick w/SkyHook & more!!! A leader in-class for a decade, Cruisers Yachts set a high bar with their 380 Exp... View Details

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$279,900
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2025 Sea Ray SLX 310

$349,152

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Bowrider
- 31' / 0'
- 2025 / New
- $349,152
Contact us to find out ALL available savings! The SLX 310 demands everyone's full attention. And by everyone we mean not only the abundance of people who can lounge comfortably onb... View Details

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$349,152
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2026 Saxdor 320 GTC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 32' / 0'
- 2026 / New
- Call for price
Act fast on this limited-time offer! Experience Ultimate Luxury with the 2025 Saxdor 320 GTC! Introducing the breathtaking 2025 Saxdor 320 GTC, where impeccable design meets exhila... View Details

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2026 Cruisers 50 Cantius

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 49' / 0'
- 2026 / New
- Call for price
Seize this exclusive opportunity! The 2026 Cruisers Yachts 50 Cantius represents the perfect balance of luxury, performance, and innovative design—continuing a legacy built on deca... View Details

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2011 Cobalt 296

$84,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 30' / 0'
- 2011 / Used
- $84,900
What an absolute creampuff!! This indoor-kept/rack-stored (summer & winter) fresh water 2011 Cobalt 296 is the discerning shopper's dream. The pictures do not deceive; in fact... View Details

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$84,900
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2026 Tiara 48LE

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 48' / 0'
- 2026 / New
- Call for price
Seize this exclusive opportunity! 2025 Tiara Yachts 48 LE Step aboard the 2025 Tiara Yachts 48 LE, where luxury meets performance. This stunning vessel features three powerful Merc... View Details

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2026 Azimut 48 Verve

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 48' / 0'
- 2026 / New
- Call for price
Seize this exclusive opportunity! The Azimut Yachts 48 Verve is a bold expression of Italian performance and luxury, redefining what a modern sport cruiser can be. Designed for own... View Details

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2008 Regal 2860 WINDOW EXPRESS

$49,995

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 29' / 0'
- 2008 / Used
- $49,995
Loved by its only owners since new, this exclusively fresh water and locally serviced Regal is awaiting a new home. She boasts a ton of space for her size with the ability to sleep... View Details

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$49,995
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Showing 190 to 210 of 1,680 boats found.

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