Boats for sale in Chicago Illinois - BoatCrazy

766 boats found within 100 miles from Chicago, Illinois

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2026 Scout 231 XSB

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 23'
- 2026 / New
- Call for price
The 2026 231 XSB is Scout's third XS model in the bay boat/inshore line-up and compliments the already popular 231 XS and 251 XSS. This model showcases up to five removable backres... View Details

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2026 Saxdor 320 GTO

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- 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 Scout 177 XSS

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- 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 Scout 255 Dorado

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 26'
- 2026 / New
- Call for price
The 255 Dorado us a dual console family-friendly sportfishing model ideal for fishing, cruising, entertaining, and watersports. One of the unique innovations onboard the model is a... View Details

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2026 Scout 277 Dorado

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 28'
- 2026 / New
- Call for price
The 2026 Scout 277 Dorado raises the bar for a family-friendly coastal fishing vessel. The custom fiberglass built-in hardtop adds to the stunning look and functionality of the mod... View Details

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2016 Regal 2100 SURF

$78,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Bowrider
- 0'
- 2016 / Used
- $78,000
New to the market is a fantastic option from Regal boats for the watersports enthusiast. This boat is loaded to the gills with just about every option you can imagine. This is a ve... View Details

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$78,000
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2021 Crownline 264 CR

$88,500

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 26'
- 2021 / Used
- $88,500
FRESHLY DETAILED, BUFFED & WAXED! Turn heads next season with this beautiful 2021 Crownline 264 CR — a perfect combination of luxury, performance, and comfort. With only 150 ho... View Details

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$88,500
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2026 Azimut Verve 42

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 42'
- 2026 / New
- Call for price
Rebellious energy and excitement come to life in the Verve 42. Forward-facing and adrenalinic, this performance-driven outboard yacht incorporates a fast and compact nature, while... 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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2009 Sea Ray 520 SUNDANCER

$439,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 52'
- 2009 / Used
- $439,900
2009 Sea Ray 520 SUNDANCER View Details

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$439,900
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2026 Galeon 410 HTC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 41'
- 2026 / New
- Call for price
Galeon's 2026 410 HTC has the same, tried-and-true hull as the builder's popular 400 FLY model, but in a sleek and sporty coupe package. The 410 combines a mega-yacht-quality inter... View Details

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2026 Galeon 375 GTO

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 38'
- 2026 / New
- Call for price
Whether you like to race around in open water at 50 mph or raft up on a lazy Sunday afternoon, the 2026 Galeon 375 GTO is the boat for you. This sleek, sporty, and versatile cruise... View Details

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2026 Sea Ray SPX 230 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 26'
- 2026 / New
- Call for price
Powerful performance, agile handling. The 2026 Sea Ray SPX 230 Outboard is built to thrill. It combines the powerful performance and agile handling you'd expect from a world-class... View Details

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2026 Sea Ray SPX 190 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 22'
- 2026 / New
- Call for price
The ultimate in fun. Discover the water like never before with the 2026 Sea Ray SPX 190 Outboard. Combining sleek aesthetics with advanced technology, this model redefins the moder... View Details

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2026 Sea Ray SPX 190

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 20'
- 2026 / New
- Call for price
Your companion for endless fun. Discover the epitome of sporty sophistication with the new 2026 Sea Ray SPX 190. Designed to deliver exhilarating thrills and timeless style, this a... View Details

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2026 Galeon 435 GTO

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 45'
- 2026 / New
- Call for price
Galeon's new 2026 Galeon 435 GTO is the yacht that can do everything you ask of her and more. This no-compromise model benefits from an entertainment-friendly layout, including a p... View Details

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2026 Sea Ray SPX 210 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 24'
- 2026 / New
- Call for price
Performance and fun. The reimagined 2026 Sea Ray SPX 210 Outboard is designed to be noticed, and delivers the next level of fun, perfect for hosting friends, sharing a casual cruis... View Details

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2026 Sea Ray SDX 290 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 31'
- 2026 / New
- Call for price
Experience Luxury and Performance with the SDX 290® Outboard. Step aboard the SDX 290® Outboard and immerse yourself in the epitome of luxury and performance. This yacht-certified... View Details

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Showing 85 to 105 of 766 boats found.

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