Boats for sale in Chicago Illinois

758 boats found within 100 miles out of 11,668 Boats Found

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2025 Scout 281 XSS

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 28'
- 2025 / New
- Call for price
Introducing the 2025 Scout 281 XSS: Step aboard the luxurious 2025 Scout 281 XSS, a masterpiece of performance and craftsmanship that promises unrivaled excitement on the water. Un... View Details

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2025 Tige Z1

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Ski & Wake
- 23'
- 2025 / New
- Call for price
Experience Luxury on the Water with the 2025 Tige Z1 Embark on a journey of unrivaled luxury and cutting-edge performance with the 2025 Tige Z1. Crafted with precision and elegance... View Details

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2025 Scout 251 XSS

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 25'
- 2025 / New
- Call for price
Experience Luxury and Performance with the 2025 Scout 251 XSS Embark on thrilling adventures with the futuristic 2025 Scout 251 XSS, boasting unparalleled craftsmanship and cutting... View Details

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2026 Cruisers 57 FLY

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 57'
- 2026 / New
- Call for price
Seize this exclusive opportunity! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat from any part... View Details

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2026 Sea Ray SLX 400

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 39'
- 2026 / New
- Call for price
Adventure awaits with the 2026 Sea Ray SLX 400. Winner of an NMMA Innovation Award, Sea Ray's SLX 400, the "The Entertainer", combines peak performance, superior comfort, incredibl... View Details

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1999 Silverton 322AFTCABIN

$39,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 32'
- 1999 / Used
- $39,900
Great opportunity to own a fresh water, 32' Silverton aft cabin. 460 hours on upgraded 454 EFI Crusaders. Newer canvas and radar/plotter, and fantastic staterooms, and salon/galley... View Details

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$39,900
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2008 Cruisers 390 SPORTS COUPE

$189,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 40'
- 2008 / Used
- $189,900
The Cruisers 390 Sports Coupe is a luxury-class express with more going for her than styling alone. One of the first builders of the era to combine a modern hardtop styling with an... View Details

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$189,900
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2026 Scout 188 Sportfish

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 19'
- 2026 / New
- Call for price
From the company that has brough many firsts to the coastal fishin boat segment, they introduce their new 188 Sportfish. This model sets a new bar by incorporating many features no... View Details

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2026 Scout 195 Sportfish

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 19'
- 2026 / New
- Call for price
This 19-footer measures 19'5" in length with a wide beam of 8'6" offering vast space to not only move around freely onboard but to also land the big catch of the day. Standard swim... View Details

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2027 Tiara EX60

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 60'
- 2027 / New
- Call for price
2027 Tiara EX60 (Stock #222103) sets the benchmark for luxury, performance, and advanced cruising features in its class. Designed for extended adventures and effortless entertainin... View Details

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2026 Sea Ray SDX 290

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 29'
- 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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2027 Azimut Fly 53

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 53'
- 2027 / New
- Call for price
2027 Azimut Fly 53 (Stock #218099) blends Italian style, advanced engineering, and luxurious comfort for exceptional on-water living. Designed for cruising and entertaining, this 5... View Details

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2026 Scout 175 Sportfish

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 17'
- 2026 / New
- Call for price
Take home a piece of engineering genius: the 2026 Scout 175 Sportfish. This stylishly-polished model delivers a vast array of fishing features, including a 94-quart removable coole... View Details

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2026 Saxdor 340 GTWA

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Performance
- 34'
- 2026 / New
- Call for price
Just landed and ready to make waves! 2026 Saxdor 340 GTWA (Stock #218345) delivers bold style, thrilling outboard power, and versatile luxury for adventure seekers. With innovative... View Details

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2022 Cruisers 338 SOUTH BEACH

$314,995

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 32'
- 2022 / Used
- $314,995
2022 Cruisers Yachts 338 South Beach – Luxury, Performance & Style, ONLY 63 HOURS ON THE ENGINES Turn heads wherever you go in this stunning 2022 Cruisers Yachts 338 South Beac... View Details

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$314,995
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2025 Scout 277 Dorado

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 28'
- 2025 / New
- Call for price
Experience Luxury with the 2025 Scout 277 Dorado Step into a world of opulence with the Scout 277 Dorado, a masterpiece of marine engineering that promises unmatched performance an... View Details

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2026 Azimut 48 Verve

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 48'
- 2026 / New
- Call for price
Seize this exclusive opportunity! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat from any part... View Details

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2020 Cobalt 200S

$34,990

Fox Lake, IL
- Fox Lake, IL
- Bowrider
- 19'
- 2020 / Used
- $34,990
Powered by a reliable Volvo Penta V6 240 HP DuoProp engine, this Cobalt delivers the smooth ride, responsive handling, and premium performance that have made the brand an industry... View Details

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$34,990
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2017 Nautique Super Air Nautique G23

$79,990

Fox Lake, IL
- Fox Lake, IL
- Ski & Wake
- 23'
- 2017 / Used
- $79,990
Powered by the PCM ZZ6 450hp direct-injection engine, this boat delivers the torque, precision, and responsiveness serious riders demand—along with the legendary reliability Nautiq... View Details

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$79,990
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2026 Cobalt R8

$270,942

Fox Lake, IL
- Fox Lake, IL
- Bowrider
- 27'
- 2026 / New
- $270,942
Cobalt R8 sets the standard for premium bowriders, combining Volvo V8-430HP performance with Cobalt’s legendary craftsmanship. Smooth, powerful, and responsive, this R8 delivers a... View Details

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$270,942
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2026 Cobalt R6

$210,242

Fox Lake, IL
- Fox Lake, IL
- Bowrider
- 25'
- 2026 / New
- $210,242
The perfect balance of luxury and performance, finished in a stunning Deep Teal exterior paired with a rich Summit/Cocoa interior that feels both modern and timeless. It’s the kind... View Details

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$210,242
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