Boats for sale in Chicago Illinois

1,609 boats found within 100 miles out of 14,295 Boats Found

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2026 Yamaha 195S

$58,964

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19'
- 2026 / New
- $58,964
Act fast on this limited-time offer! Introducing the 2026 Yamaha 195S, affordable luxury features at 19-feet. High-tech features, sleek design, and top-notch performance create the... View Details

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$58,964
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2024 Tiara 38LS

$729,995

Pewaukee, WI
- Pewaukee, WI
- Fishing Center Console
- 38'
- 2024 / Used
- $729,995
2024 Tiara Yachts 38LS View Details

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$729,995
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2026 Barletta Corsa 23 QCSS

$116,891

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2026 / New
- $116,891
Act fast on this limited-time offer! Discover the Pinnacle of Luxury Introducing the 2026 Barletta CORSA23QCSS, where cutting-edge design meets unparalleled craftsmanship. This sle... View Details

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$116,891
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2026 Barletta S22QC

$71,967

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 22'
- 2026 / New
- $71,967
Experience Unmatched Luxury The 2026 Barletta SANZA22QC is the epitome of luxury on water, designed for those who appreciate the finer things in life. Crafted with meticulous atten... View Details

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$71,967
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2026 Barletta Reserve Leggera 23 UCA

$268,360

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25'
- 2026 / New
- $268,360
Act fast on this limited-time offer! Experience Unmatched Luxury Introducing the 2026 Barletta RESERVELEGGERA23UCA, a pinnacle of marine sophistication. Crafted for those who seek... View Details

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$268,360
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2026 Barletta Cabrio 24 U

$105,187

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25'
- 2026 / New
- $105,187
Act fast on this limited-time offer! Experience Unmatched Luxury Introducing the stunning 2026 Barletta CABRIO24U, where elegance meets adventure. This new vessel is designed for t... View Details

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$105,187
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2025 Cruisers 60 CANTIUS

$2,549,000

Pewaukee, WI
- Pewaukee, WI
- Yacht
- 60'
- 2025 / Used
- $2,549,000
Just Listed: 2025 Cruisers Yachts 60 Cantius – Virtually New. Freshwater. Fully Loaded. Step aboard this titled, never-used 2025 Cruisers Yachts 60 Cantius — a yacht that has never... View Details

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$2,549,000
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2026 Yamaha SX220

$65,133

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 22'
- 2026 / New
- $65,133
Act fast on this limited-time offer! Introducing the 2026 Yamaha SX220, unmatched value, versatility, and affordability. With its roomy cockpit, abundant storage, and fuel-efficien... View Details

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$65,133
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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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2026 Barletta Aria 24 UC

$72,132

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2026 / New
- $72,132
Act fast on this limited-time offer! Welcome Aboard the Future Introducing the stunning 2026 Barletta ARIA24UC, where luxury meets exhilarating performance. This remarkable vessel... View Details

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$72,132
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2026 Yamaha AR220

Call for price

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 22'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha AR220, value-packed watersports fun. Offering the perfect blend of value, versatility, and convenience in an affordable 22-foot package. Key Features Pe... View Details

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2015 Chaparral SUNESTA 264

$62,652

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 26'
- 2015 / Used
- $62,652
The 2015 Chaparral SUNESTA 264 combines thrilling performance with comfort and style, making it a standout choice for boating adventures on Pewaukee Lake. Powered by a robust Volvo... View Details

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$62,652
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2014 Tige R20

$39,962

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20'
- 2014 / Used
- $39,962
Hop aboard the 2014 Tige R20—a showstopper on Pewaukee Lake! Featuring a vibrant yellow fiberglass hull and a powerful Indmar FUSION 335 engine (335 HP), this vessel delivers excit... View Details

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$39,962
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2012 Harris 230 GRAND MARINER

$20,334

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2012 / Used
- $20,334
Imagine gliding across Pewaukee Lake in the 2012 Harris 230 GRAND MARINER—a pontoon built for both relaxation and fun. Outfitted with a Mercury 115HP outboard engine and an advance... View Details

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$20,334
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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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2026 Yamaha AR220

$68,812

Pewaukee, WI
- Pewaukee, WI
- Jet boat
- 22'
- 2026 / New
- $68,812
Act fast on this limited-time offer! 2026 Yamaha 220AR Step aboard the 2026 Yamaha 220AR, where luxury meets performance on the water. With its sleek lines and impeccable craftsman... View Details

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$68,812
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2022 Sea Ray 250 SDX

$119,500

Pewaukee, WI
- Pewaukee, WI
- Runabout
- 25'
- 2022 / Used
- $119,500
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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$119,500
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2004 Starcraft ELITE 226

$14,864

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25'
- 2004 / Used
- $14,864
Step aboard the 2004 Starcraft ELITE 226 and experience Pewaukee’s lake life in comfort and style. Powered by a reliable Mercury 50HP outboard engine and supported by an advanced h... View Details

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$14,864
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2021 Yamaha SX 210

$38,995

Pewaukee, WI
- Pewaukee, WI
- Jet boat
- 21'
- 2021 / Used
- $38,995
The 2021 Yamaha SX210 is a 21-foot jet boat known for its blend of luxury, versatility, and value. Featuring twin Yamaha TR-1 High Output engines. Enjoy various activities like cru... View Details

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$38,995
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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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2007 Four Winns 204 FS

$18,995

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 21'
- 2007 / Used
- $18,995
2007 Four Winns 204 FS View Details

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$18,995
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