Boats for sale in Chicago Illinois

1,753 boats found within 100 miles out of 16,010 Boats Found

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2018 Carver C37

$389,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 37' / 0'
- 2018 / Used
- $389,995
2018 Carver 37 Coupe – Freshwater Kept |Two-Owner Vessel This 2018 Carver 37 Coupe offers an exceptional opportunity to enjoy the popular coupe-style cruising experience at a very... View Details

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$389,995
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2024 Tiara 38LS

$729,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 38' / 0'
- 2024 / Used
- $729,995
2024 Tiara Yachts 38LS View Details

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$729,995
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2022 Heyday H22

$68,086

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22' / 0'
- 2022 / Used
- $68,086
Sale Price: $69,900 View Details

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$68,086
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2021 ATX Surf Boats 20 TYPE-S

$62,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20' / 0'
- 2021 / Used
- $62,995
Take advantage of limited-time savings on in-stock boats!Luxury Elevated: 2021 ATX Surf Boats 20TYPES Unleash your passion for the water with the 2021 ATX Surf Boats 20TYPES, a per... View Details

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$62,995
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2023 Malibu 20 VTX

$114,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 23' / 0'
- 2023 / Used
- $114,995
Take advantage of limited-time savings on in-stock boats!Experience Adventure on the Water Unleash your passion for adrenaline and water sports with the 2023 Malibu 20 VTX, an icon... View Details

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$114,995
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2008 Glastron GT225

$18,995

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 22' / 0'
- 2008 / Used
- $18,995
Take advantage of limited-time savings on in-stock boats!2008 Glastron GT225: Accelerate your summer with this 2008 Glastron GT225!!. This pre-owned vessel is clean and ready for a... View Details

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$18,995
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2018 Sylvan 8522

$18,995

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 22' / 0'
- 2018 / Used
- $18,995
Take advantage of limited-time savings on in-stock boats!Experience Luxury on the Water Step aboard the 2018 Sylvan 8522, where luxury meets exhilarating performance. Designed for... View Details

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$18,995
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2008 Glastron SX175

$9,995

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 17' / 0'
- 2008 / Used
- $9,995
Take advantage of limited-time savings on in-stock boats!Embark on Unforgettable Adventures Imagine gliding across the serene waters of Pewaukee, WI, with the sleek and stylish 200... View Details

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$9,995
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2025 Yamaha 220 SX

$52,132

Pewaukee, WI
- Pewaukee, WI
- Jet boat
- 22' / 0'
- 2025 / New
- $52,132
Contact us to find out ALL available savings! Featuring a spacious cockpit, generous storage and total package of features, the SX220 is a game changer in the 22-foot segment. View Details

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$52,132
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2025 Bayliner D20I

$48,596

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 19' / 0'
- 2025 / New
- $48,596
Contact us to find out ALL available savings! 2025 Bayliner D20I Step aboard the 2025 Bayliner D20I and experience the perfect blend of luxury and performance. Designed for both th... View Details

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$48,596
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2025 Yamaha 220 AR

$54,227

Pewaukee, WI
- Pewaukee, WI
- Jet boat
- 22' / 0'
- 2025 / New
- $54,227
Act fast on this limited-time offer! 2025 Yamaha 220AR Step into the world of luxury boating with the brand-new 2025 Yamaha 220AR, where performance meets elegance. Experience the... View Details

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$54,227
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2025 Bayliner D20

$47,447

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 20' / 0'
- 2025 / New
- $47,447
Contact us to find out ALL available savings! The D20 outboard model is perfect for families looking for versatility and comfort on the water. With two different interior floorplan... View Details

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$47,447
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2025 Bayliner V20I

$51,501

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 20' / 0'
- 2025 / New
- $51,501
Contact us to find out ALL available savings! 2025 Bayliner V20I Experience the pinnacle of luxury boating with the exquisite 2025 Bayliner V20I, now available at SkipperBud's Pewa... View Details

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$51,501
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2025 Bayliner D20I

$48,596

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 20' / 0'
- 2025 / New
- $48,596
Contact us to find out ALL available savings! Luxury Redefined: The 2025 Bayliner D20I Sleek Design: The Bayliner D20I exudes sophistication and style, boasting a modern design tha... View Details

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$48,596
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2025 Yamaha 220 AR

$54,227

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 22' / 0'
- 2025 / New
- $54,227
Act fast on this limited-time offer! Experience Luxury on Water Step aboard the 2025 Yamaha 220AR, where unparalleled craftsmanship meets cutting-edge design. This luxurious vessel... View Details

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$54,227
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2026 Starcraft SVX 191 OB

Call for price

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 18' / 0'
- 2026 / New
- Call for price
Just landed and ready to make waves! Starcraft's SVX 191 OB fiberglass sport boat is tailored for family adventures, offering a thrilling combination of speed and comfort on the wa... View Details

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2026 Yamaha AR220

$70,376

Pewaukee, WI
- Pewaukee, WI
- Jet boat
- 22' / 0'
- 2026 / New
- $70,376
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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$70,376
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2022 Barletta LUSSO 23UCTT

$89,995

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2022 / Used
- $89,995
2022 Barletta LUSSO 23UCTT View Details

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$89,995
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2004 Starcraft ELITE 226

$14,864

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2004 / Used
- $14,864
Discover Your Dream: 2004 Starcraft ELITE 226 Step aboard the 2004 Starcraft ELITE 226 and experience the ultimate blend of luxury and performance. This elegant vessel is crafted f... View Details

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$14,864
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2021 Barletta L23QC

$80,209

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2021 / Used
- $80,209
2021 Barletta L23QC: Luxury Awaits Discover the ultimate on-water experience with the 2021 Barletta L23QC. This luxurious boat combines exceptional craftsmanship with advanced tech... View Details

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$80,209
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2014 Tige R20

$39,962

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20' / 0'
- 2014 / Used
- $39,962
Experience Unmatched Performance Step aboard the 2014 Tige R20, where exhilarating performance meets cutting-edge design. Powered by a robust INDMAR FUSION 335 engine, this luxury... View Details

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$39,962
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