Boats for sale in Chicago Illinois

812 boats found within 100 miles from Chicago, Illinois

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2026 Yamaha 222S

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Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 22'
- 2026 / New
- Call for price
The 2026 Yamaha 222S, timeless style, premium performance. The 222S combines timeless styling, premium refinements, and class-leading performance in an affordable 22-foot package.... View Details

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2024 Yamaha AR220

$49,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 22'
- 2024 / Used
- $49,995
The perfect blend of power, sophistication, and versatility. This sleek and stylish sport boat is designed for the ultimate thrill-seekers and water sports enthusiasts. Boasting a... View Details

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$49,995
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2026 Yamaha SX190

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Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19'
- 2026 / New
- Call for price
A perfect welcome to the water. The 2026 Yamaha SX190 can promise hassle-free ownership with innovative features and sleek design at an afforable price. The Yamaha SX190 is easy to... View Details

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2026 Yamaha AR195

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Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19'
- 2026 / New
- Call for price
Introducing your 2026 Yamaha AR195, supercharge your Saturdays. Enjoy unparalleled supercharged performance, standout styling, and incredible value, all enhanced by a watersports t... View Details

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2018 Sea Ray 350 SUNDANCER

$279,495

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 35'
- 2018 / Used
- $279,495
🌊 ONE OWNER • FRESHWATER ONLY • UNDER 300 HOURS • LOADED WITH OPTIONS • IMPECCABLY MAINTAINED 🌊 Opportunity Knocks! This exceptional Sea Ray 350 Sundancer is the kind of boat dis... View Details

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$279,495
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2026 Barletta Cabrio 24 UE

$98,170

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25'
- 2026 / New
- $98,170
Act fast on this limited-time offer! Experience Ultimate Luxury at Sea The 2026 Barletta CABRIO24UE epitomizes elegance and performance. With cutting-edge design and meticulous cra... View Details

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$98,170
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2022 Sea Ray 250 SDX

$99,995

Pewaukee, WI
- Pewaukee, WI
- Runabout
- 25'
- 2022 / Used
- $99,995
The 2022 Sea Ray 250 SDX is the perfect blend of luxury, performance, and versatility. Whether you’re looking for a high-performance boat for watersports or a comfortable vessel fo... View Details

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$99,995
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2021 ATX Surf Boats 20 TYPE-S

$79,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20'
- 2021 / Used
- $79,995
Own the water with this 2021 ATX 20 Type-S. Compact size meets full-size performance for every watersport imaginable-from catching the perfect surf wave to throwing down rampy wake... View Details

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$79,995
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2004 Centurion AVALANCHE C4

$24,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22'
- 2004 / Used
- $24,995
Thie Centurion will put a smile on your face as soon as you hear the big V8 with the thru hull exhaust! Get into a great performance tow boat without breaking the bank. Come on dow... View Details

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$24,995
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2022 Barletta LUSSO 23UCTT

$89,995

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2022 / Used
- $89,995
2022 Barletta LUSSO 23UCTT View Details

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$89,995
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1997 Sea Ray 330 EXPRESS CRUISER

$49,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 33'
- 1997 / Used
- $49,995
🎣 Freshwater Fishing Machine! This 1997 Sea Ray 330 Express Cruiser has been professionally repowered with twin 8.1L MPI engines featuring digital shift and throttle, delivering m... View Details

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$49,995
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2005 Bentley 240 CRUISE

$10,097

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 24'
- 2005 / Used
- $10,097
2005 Bentley 240 CRUISE Step aboard the 2005 Bentley 240 CRUISE and experience the perfect blend of performance and luxury on the water. This stunning vessel, with its elegant desi... View Details

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$10,097
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2016 Sea Ray 190 SPX

$18,995

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 19'
- 2016 / Used
- $18,995
2016 Sea Ray 190 SPX, powered by Mercruiser 4.3L 190HP. This boat has had only two previous owners and is in Immaculate condition, always stored indoors and ready for the water. Eq... View Details

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$18,995
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2026 Barletta Corsa

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 0'
- 2026 / New
- Call for price
Introducing the 2026 Barletta Corsa Luxury Boat Experience the epitome of luxury and performance with the 2026 Barletta Corsa, a masterpiece of craftsmanship and innovation. Luxuri... View Details

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2006 Formula 330 SS

$83,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 33'
- 2006 / Used
- $83,995
2006 Formula 330 SS View Details

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$83,995
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2026 Barletta Cabrio

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 0'
- 2026 / New
- Call for price
Introducing the 2025 Barletta Cabrio Experience the epitome of luxury and style with the 2026 Barletta Cabrio. Crafted with precision and attention to detail, this masterpiece prom... View Details

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2026 Harris Breeze 210

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 0'
- 2026 / New
- Call for price
Easy does it with the 2026 Harris Breeze 210. No frills, all fun. Harris made a simple boat that covers all your needs without the costly extra features. The Breeze is for those wh... View Details

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2026 Barletta Aria

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 0'
- 2026 / New
- Call for price
Introducing the 2026 Barletta Aria Experience the pinnacle of luxury and performance with the 2026 Barletta Aria. Embark on unforgettable journeys filled with excitement and elegan... View Details

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2026 Harris Cruiser 250

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 26'
- 2026 / New
- Call for price
Introducing the 2026 Harris Cruiser 250, built without compromise. Invite your friends waterskiing, take the kids for a sun-soaked day of cruising, or escape alone and cast a line.... View Details

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2022 Heyday H22

$60,136

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22'
- 2022 / Used
- $60,136
Sale Price: $69,900 View Details

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$60,136
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2023 Starcraft 211 SVX

$49,995

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 21'
- 2023 / Used
- $49,995
2023 Starcraft 211 SVX View Details

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$49,995
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