Boats for sale in Chicago Illinois - BoatCrazy

1,782 boats found within 100 miles out of 15,686 Boats Found

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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 Harris 230 Cruiser

$49,300

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $49,300
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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$49,300
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2025 Harris 230 Cruiser

$49,867

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $49,867
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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$49,867
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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 Harris 230 Cruiser

$50,187

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $50,187
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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$50,187
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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 Yamaha SX195

Call for price

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha SX195, built to elevate your weekends. Experience unrivaled supercharged performance, striking styling, and exceptional value in its class. Key Features... View Details

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2022 Mastercraft XT 24

$149,980

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 24' / 0'
- 2022 / Used
- $149,980
366 Hours Explore the 2022 Masc XT 24 Step aboard the 2022 Masc XT 24, where luxury meets performance on the water. This stunning vessel, available at SkipperBud's Pewaukee in Pewa... View Details

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$149,980
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2026 Barletta S22QC

$71,967

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 22' / 0'
- 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 Yamaha SX190

Call for price

Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 19' / 0'
- 2026 / New
- Call for price
Immerse Yourself in Luxury Introducing the 2026 Yamaha 190SX, a stunning blend of performance and elegance that invites you to embark on unforgettable water adventures. With its sl... View Details

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2026 Yamaha 195S

$60,305

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19' / 0'
- 2026 / New
- $60,305
Introducing the 2026 Yamaha 195S, affordable luxury features at 19-feet. High-tech features, sleek design, and top-notch performance create the ultimate affordable 19-foot boat pac... View Details

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$60,305
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2026 Yamaha AR195

$58,085

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19' / 0'
- 2026 / New
- $58,085
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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$58,085
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2025 Mastercraft NXT20

$110,275

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20' / 0'
- 2025 / New
- $110,275
Act fast on this limited-time offer! Explore the Waves in Style with the NXT20 Discover the perfect combination of affordability and excitement with the NXT20 boat. Measuring 20 fe... View Details

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$110,275
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2025 Harris 230 Solstice

$101,543

Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 23' / 0'
- 2025 / New
- $101,543
Contact us to find out ALL available savings! Introducing the 2025 Harris 230 Solstice Luxury Redefined Step aboard the epitome of elegance and performance with the 2025 Harris 230... View Details

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$101,543
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2025 Harris 230 Cruiser

$69,615

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $69,615
Act fast on this limited-time offer! Experience Unmatched Adventure Introducing the 2025 Harris 230 Cruiser CWDH, where luxury meets performance on the water. Crafted for those who... View Details

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$69,615
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2025 Barletta LUSSO25UE

$141,296

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $141,296
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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$141,296
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2025 Barletta LUSSO25UC

$137,288

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $137,288
Contact us to find out ALL available savings! BARLETTA LUSSO 25 UC 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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$137,288
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2025 Barletta LUSSO23UC

$114,732

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $114,732
Contact us to find out ALL available savings! BARLETTA LUSSO 25 UC 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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$114,732
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2025 Barletta ARIA20CC

$48,131

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 20' / 0'
- 2025 / New
- $48,131
Contact us to find out ALL available savings! BARLETTA ARIA 20 CC Everything you love about the Barletta DNA with a price conscious approach. Is the Aria right for you? Designed to... View Details

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$48,131
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Showing 1408 to 1428 of 1,782 boats found.

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