Boats for sale in Chicago Illinois - BoatCrazy

747 boats found within 100 miles out of 11,762 Boats Found

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2026 Mastercraft NXT20

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Walworth, WI
- Walworth, WI
- Ski & Wake
- 20'
- 2026 / New
- Call for price
Introducing the 2026 MasterCraft NXT24-big, bold, and built to deliver-waves, comfort, and style all in one serious package. At 24 feet, it's the largest in the XT lineip with room... View Details

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2026 Sailfish 272 CC

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Walworth, WI
- Walworth, WI
- Fishing Center Console
- 27'
- 2026 / New
- Call for price
The 2026 Sailfish 272 center console offers next-level comfort with ample fish-fighting room. Enjoy smooth, powerful performance courtesy of the 6th-generation VDS hull design, and... View Details

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2026 Mastercraft XT24

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Walworth, WI
- Walworth, WI
- Ski & Wake
- 24'
- 2026 / New
- Call for price
The 2026 MasterCraft XT24-big, bold, and built to deliver-waves, comfort, and style all in one serious package. At 24 feet, it's the largest in the XT lineup with room for 17 and 3... View Details

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2026 Sailfish 242 CC

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Walworth, WI
- Walworth, WI
- Fishing Center Console
- 24'
- 2026 / New
- Call for price
Designed and built for offshore anglers, the 242 center console features the Sailfish VDS hull, ensuring smooth, powerful performance. With its larger console headspace, ample seat... View Details

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2026 Sailfish 360 CC

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Walworth, WI
- Walworth, 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 Sailfish 241 CC

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Walworth, WI
- Walworth, 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 Sailfish 316 DC

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Walworth, WI
- Walworth, WI
- Runabout
- 33'
- 2026 / New
- Call for price
The new 316 dual console is a versatile family fishing boat that checks all the boxes: comfort, safety, quality and reliability. Well-equipped for a range of activities, the 316 DC... View Details

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2026 Sailfish 276 DC

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Walworth, WI
- Walworth, WI
- Runabout
- 29'
- 2026 / New
- Call for price
Incredible versatility and comfort are hallmarks of the 276 dual console. A 6th-generation VDS hull ensures a soft, dry ride, while the spacious, ergonomic deck design and an array... View Details

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2026 Sailfish 232 CC

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Walworth, WI
- Walworth, WI
- Fishing Center Console
- 23'
- 2026 / New
- Call for price
Center consolde spaciousness meets family-friendly versatility in the Sailfish 232 center console. With an array of features and options for fishing trips and fun-filled outings, t... View Details

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2026 Sailfish 245 DC

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Walworth, WI
- Walworth, WI
- Runabout
- 24'
- 2026 / New
- Call for price
With comfortable seating for 12, a spacious step-down head and an optiona cockpit galley, the 245 dual console is designed for active families as well as serious offshore anglers.... View Details

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2026 Sailfish 312 CC

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Walworth, WI
- Walworth, 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 Saxdor 270 GTO

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Walworth, WI
- Walworth, WI
- Runabout
- 0'
- 2026 / New
- Call for price
Experience the epitome of luxury and performance with the Saxdor 270 GTO. Designed for those who demand the best on the water, this sleek vessel embodies sophistication and style.... View Details

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2004 Chaparral 280 SSi

$39,995

Waterford, WI
- Waterford, WI
- Bowrider
- 28'
- 2004 / Used
- $39,995
Stock #487201 Video of this vessel available at www [dot] popsells [dot] com/view/487201 Reason for selling is "Buying a smaller boat". This Chaparral has now been on the market... View Details

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$39,995
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2019 Supra SA400

$115,000

Delavan, WI
- Delavan, WI
- Ski & Wake
- 25'
- 2019 / Used
- $115,000
Stock #360586 Reason for selling is "Plans changed". ANY and ALL offers will be put in front of our seller! Submit your offer today! 350HP INDMAR! TRAILER INCLUDED!! READY TO PL... View Details

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$115,000
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1999 Sea Ray 500 Sundancer

$197,000

South Haven, MI
- South Haven, MI
- Express Cruiser
- 50'
- 1999 / Used
- $197,000
Stock #471094 Video of this vessel available at www [dot] popsells [dot] com/view/471094 Reason for selling is "Has not used enough". ANY and ALL offers will be put in front of... View Details

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$197,000
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2014 Crestliner 1650 Fish Hawk SC

$16,500

Brookfield, WI
- Brookfield, WI
- Fishing
- 16'
- 2014 / Used
- $16,500
Crestliner 1650 Fish Hawk SC - Your Ultimate Fishing Companion Experience the thrill of fishing with the Crestliner 1650 Fish Hawk SC, a boat designed for anglers who demand perfo... View Details

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$16,500
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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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Showing 442 to 462 of 747 boats found.

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