Boats for sale in Chicago Illinois

1,753 boats found within 100 miles out of 16,479 Boats Found

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2004 Centurion AVALANCHE C4

$24,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22' / 0'
- 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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2021 Yamaha SX 210

$38,995

Pewaukee, WI
- Pewaukee, WI
- Jet boat
- 21' / 0'
- 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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2003 Sea Ray 550 SUNDANCER

$334,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 55' / 0'
- 2003 / Used
- $334,995
2003 Sea Ray 550 Sundancer – Turn-Key Luxury with Extensive Upgrades This impeccably maintained 2003 Sea Ray 550 Sundancer combines proven performance, refined comfort, and timel... View Details

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$334,995
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1997 Sea Ray 330 EXPRESS CRUISER

$59,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 33' / 0'
- 1997 / Used
- $59,995
1997 Sea Ray 330 EXPRESS CRUISER View Details

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$59,995
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2007 Four Winns 204 FS

$18,995

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 21' / 0'
- 2007 / Used
- $18,995
2007 Four Winns 204 FS View Details

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$18,995
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2021 ATX Surf Boats 20 TYPE-S

$67,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20' / 0'
- 2021 / Used
- $67,995
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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$67,995
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2026 Barletta Cabrio 24 UE

$99,995

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2026 / New
- $99,995
Act fast on this limited-time offer! Introducing the 2026 Barletta CABRIO24UE Experience unparalleled luxury on the water with the stunning 2026 Barletta CABRIO24UE. Designed with... View Details

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$99,995
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2016 Sea Ray 190 SPX

$18,995

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 19' / 0'
- 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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1998 Malibu SPORTSTER

$14,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 0' / 0'
- 1998 / Used
- $14,995
For skiers who crave pure performance and a classic design, The 1998 Malibu Sportster LX delivers. This nimble 20 foot inboard is known for its excellent slalom wake and responsive... View Details

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$14,995
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2026 Yamaha SX195

$56,104

Pewaukee, WI
- Pewaukee, WI
- Jet boat
- 19' / 0'
- 2026 / New
- $56,104
Act fast on this limited-time offer! 2026 Yamaha 195SX Step into the world of luxury and adventure with the brand-new 2026 Yamaha 195SX, available at SkipperBud's Pewaukee in Pewau... View Details

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$56,104
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2020 Mastercraft X22

$106,421

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22' / 0'
- 2020 / Used
- $106,421
The X22 is an absolute surf beast and has a wave that is right for everyone. Whether you are a surf enthusiast, or just a weekend warrior, the X22 won't disappoint. Give us a call... View Details

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$106,421
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2023 Starcraft 211 SVX

$49,995

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 21' / 0'
- 2023 / Used
- $49,995
2023 Starcraft 211 SVX View Details

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$49,995
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2002 Larson 210 SEI

$10,180

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 21' / 0'
- 2002 / Used
- $10,180
This 2002 Larson 210 looking for a new home! This pre-owned bowrider has 600 engine hours and is ready for another 400 with you and your family. This boat features a Yamaha 175HP O... View Details

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$10,180
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2010 Sea Ray 260 SUNDECK

$45,000

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 0' / 0'
- 2010 / Used
- $45,000
The 2010 Sea Ray 260 Sundeck is a premium boat designed for comfort, performance, and entertaining on the water. At 26 feet in length, it offers an exceptionally spacious layout wi... View Details

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$45,000
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2005 Bentley 240 CRUISE

$10,097

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 24' / 0'
- 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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2025 Mastercraft XSTAR

$354,977

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 23' / 0'
- 2025 / New
- $354,977
Act fast on this limited-time offer! Experience Unmatched Performance Introducing the 2025 Mastercraft XSTAR, where cutting-edge engineering meets exhilarating performance. This st... View Details

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$354,977
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2025 Mastercraft NXT22

$128,525

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22' / 0'
- 2025 / New
- $128,525
Contact us to find out ALL available savings! The fresh new MasterCraft NXT22 is big news. One of our most popular boats ever has a brand new design and updates from tip to tail. T... View Details

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$128,525
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2025 Sea Ray SDX 270

$182,584

Pewaukee, WI
- Pewaukee, WI
- Runabout
- 27' / 0'
- 2025 / New
- $182,584
Contact us to find out ALL available savings! The SDX 270 delivers on maximum capability to make a full day on the water easy to enjoy. With plenty of seating, storage space and pr... View Details

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$182,584
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2025 Harris 210 Cruiser

$55,022

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $55,022
Contact us to find out ALL available savings! Invite your friends waterskiing, take the kids for a sun-soaked day of cruising, or escape alone and cast a line. No matter what you d... View Details

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$55,022
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2025 Barletta LUSSO25UE

$135,131

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $135,131
Contact us to find out ALL available savings! BARLETTA LUSSO 25 UE Is Lusso right for you? Designed with you, and your on-water experience, in mind, the Barletta Lusso models offer... View Details

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$135,131
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2026 Barletta Corsa 25 UC

$133,243

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2026 / New
- $133,243
Act fast on this limited-time offer! Discover the 2026 Barletta CORSA25UC Experience the pinnacle of luxury on the open water with the stunning 2026 Barletta CORSA25UC. This vessel... View Details

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$133,243
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