Boats for sale in Chicago Illinois - BoatCrazy

733 boats found within 100 miles out of 11,627 Boats Found

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2026 Harris Solstice 250

$149,615

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 26'
- 2026 / New
- $149,615
Act fast on this limited-time offer! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat from any p... View Details

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$149,615
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2024 Bayliner M19

$33,995

Pewaukee, WI
- Pewaukee, WI
- Runabout
- 19'
- 2024 / Used
- $33,995
This is a Skipperbud’s Certified Pre-Owned Vessel. Every Skipperbud’s Certified Pre-Owned boat undergoes a 360° bow-to-stern inspection by Skipperbud’s Certified technicians, and i... View Details

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$33,995
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2026 Harris Solstice 230

$110,781

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25'
- 2026 / New
- $110,781
Act fast on this limited-time offer! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat from any p... View Details

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$110,781
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2023 Malibu 20 VTX

$114,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 23'
- 2023 / Used
- $114,995
Take advantage of limited-time savings on in-stock boats!2023 Malibu 20 VTX Experience unmatched luxury and performance with the 2023 Malibu 20 VTX, the ultimate vessel for water e... View Details

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$114,995
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2025 Barletta LUSSO25UE

$141,296

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25'
- 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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2026 Harris 230 Grand Mariner

$157,465

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 26'
- 2026 / New
- $157,465
Act fast on this limited-time offer! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat from any p... View Details

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$157,465
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2025 Barletta ARIA20CC

$47,957

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 20'
- 2025 / New
- $47,957
Contact us to find out ALL available savings! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat f... View Details

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$47,957
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2025 Barletta LUSSO25UC

$137,288

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25'
- 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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2026 Harris Cruiser 190

$40,768

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 20'
- 2026 / New
- $40,768
Act fast on this limited-time offer! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat from any p... View Details

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$40,768
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2025 Bayliner VR4OB

$36,040

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 18'
- 2025 / New
- $36,040
Contact us to find out ALL available savings! Act fast on this limited-time offer! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase o... View Details

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$36,040
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2026 Sea Ray SPX 210 Outboard

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Pewaukee, WI
- Pewaukee, WI
- Runabout
- 21'
- 2026 / New
- Call for price
Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat from any participating SkipperBud's locati... View Details

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2025 Trophy CC22

$79,995

Pewaukee, WI
- Pewaukee, WI
- Fishing Sportfish / Convertible
- 22'
- 2025 / New
- $79,995
Contact us to find out ALL available savings! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat f... View Details

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$79,995
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2023 Mastercraft X22

$159,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22'
- 2023 / New
- $159,995
Contact us to find out ALL available savings! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat f... View Details

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$159,995
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2025 Starcraft RX 23 DL DHTT

$105,078

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2025 / New
- $105,078
Contact us to find out ALL available savings! Act fast on this limited-time offer! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase o... View Details

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$105,078
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2026 Sailfish 312 CC

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Pewaukee, WI
- Pewaukee, WI
- Fishing Center Console
- 31'
- 2026 / New
- Call for price
The all-new 2026 Sailfish center console offers an incredible VDS hull design for fuel efficiency and comfort, a striking appearance, ample space, and prioritized safety. It has ev... View Details

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2026 Sailfish 360 CC

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Pewaukee, WI
- Pewaukee, WI
- Fishing Center Console
- 39'
- 2026 / New
- Call for price
The flagship 360 center console combines unsurpassed quality and state-of-the-art technology with a layout and features designed for maximum versatility. Fish, play, cruise or ente... View Details

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2026 Saxdor 400 GTC

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Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 41'
- 2026 / New
- Call for price
The Saxdor 400 GTC is engineered for twin outboard rigs with their unique naval architecture, guaranteeing an unforgettable journey every time. Featuring an innovative main deck de... View Details

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2026 Scout 177 XSS

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Pewaukee, WI
- Pewaukee, WI
- Fishing Center Console
- 18'
- 2026 / New
- Call for price
Introducing the sleek and sporty 2026 Scout 177 XSS; perfectly blending style and performance, this versatile boat is designed to enhance your on-water adventures. Its compact yet... View Details

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2026 Sailfish 241 CC

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Pewaukee, WI
- Pewaukee, WI
- Fishing Center Console
- 24'
- 2026 / New
- Call for price
With its sleek, dynamic profile and 6th generation VDS hull, combined with a highly functional layout and long-lasting Sailtech Construction, the 241 center console is a powerful f... View Details

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2026 Saxdor 320 GTO

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Pewaukee, WI
- Pewaukee, WI
- Runabout
- 34'
- 2026 / New
- Call for price
The Saxdor 320 GTO has been Saxdor's bestselling model for many years and is a highly appreciated global success story that is irresistible across the globe. It combines phenomenal... View Details

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2026 Saxdor 320 GTC

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Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 34'
- 2026 / New
- Call for price
You choose the weather. The Saxdor 320 GTC drives like no other because of its refined, economic and performance-oriented hull design. A lower center of gravity, low weight, sharp... View Details

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Showing 484 to 504 of 733 boats found.

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