Boats for sale in Chicago Illinois - BoatCrazy

1,625 boats found within 100 miles out of 14,319 Boats Found

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2025 Aviara AV32 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 34'
- 2025 / New
- Call for price
Experience Luxury with the 2025 Aviara AV32 Outboard Step aboard the epitome of sophistication and performance with the 2025 Aviara AV32 Outboard. Crafted to perfection by Aviara,... View Details

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2025 Aviara AV36

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 37'
- 2025 / New
- Call for price
Introducing the 2025 Aviara AV36: Experience the ultimate luxury on water with the Aviara AV36, a masterpiece of design and performance. Luxurious Craftsmanship: An exquisite blend... View Details

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2025 Aviara AV40 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 42'
- 2025 / New
- Call for price
2025 Aviara AV40 Outboard Experience the epitome of luxury and performance with the 2025 Aviara AV40 Outboard. Crafted with meticulous attention to detail, this stunning vessel is... View Details

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2024 Aviara AV32

$369,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Bowrider
- 32'
- 2024 / New
- $369,000
Contact us to find out ALL available savings! Aviara has redefined the modern day boat to bring you true luxury. This is the fusion of progressive design and effortless comfort, th... View Details

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$369,000
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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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1982 Ericson 36 Ron Holland Edition

$22,500

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Sailboat
- 36'
- 1982 / Used
- $22,500
Stock #477838 Reason for selling is "Not using it enough.". This Ericson Yachts has now been on the market a couple months. Looking for any offers! 1982 Ericson 36 Sailboat (Ron... View Details

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$22,500
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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
Built for fun, introducing the 2026 Sea Ray SDX 290. When an active family loves water sports, they generall want to share their good times with friends. That's where the SDX 290 c... View Details

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2026 Sea Ray SLX 260 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 28'
- 2026 / New
- Call for price
Discover the Sea Ray SLX 260 Outboard - An Award-Winning Masterpiece Step aboard the Sea Ray SLX 260 Outboard and prepare to be amazed. Winner of the 2023 Miami Innovation Award in... View Details

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2026 Sea Ray Sundancer 320 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 32'
- 2026 / New
- Call for price
The value of a cruiser and a sport-combined. Introducing the 2026 Sea Ray Sundancer 320 Outboard. Combining the values of a cruiser and a sport-boat/bowrider in a brilliant package... 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
Built for fun, introducing the 2026 Sea Ray SDX 290. When an active family loves water sports, they generall want to share their good times with friends. That's where the SDX 290 c... View Details

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2022 Harris HCX 230 SL

$30,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Pontoon
- 23'
- 2022 / Used
- $30,000
The 2022 Harris CR 230 Sunliner offers a chance to get into a late-model pontoon with modern styling and comfort—without paying full new-boat pricing. While it’s still a used boat,... View Details

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$30,000
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2021 Crownline 264 CR

$98,500

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 26'
- 2021 / Used
- $98,500
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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$98,500
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2021 Sea Ray 270 SDX

$114,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Deck Boat
- 27'
- 2021 / Used
- $114,900
This is a great opportunity for a pre owned, fresh water, popular 270SDX. I can furnish you with the original Sea Ray factory options, we sold it to the folks when it was new and a... View Details

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$114,900
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2026 Yamaha 252S

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25'
- 2026 / New
- Call for price
Luxury, Technology, and premium refinements all define the 2026 Yamaha 252S. Combining luxury and technology with premium refinements in a timeless design, the 252S turns heads and... View Details

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2026 Yamaha 252SE

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha 252SE a premium boating experience. The 252SE, equipped with Yamaha E-Series features, redefined modern style, technology, and convenience. Key Features... View Details

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2026 Yamaha 252SD

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25'
- 2026 / New
- Call for price
The future is now with the 2026 Yamaha 252SD. Introducing DRiVE X, the next evolution of Yamaha's DRiVE technology, revolutionizing boat maneuverability. With this advanced system,... View Details

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2026 Yamaha SX250

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25'
- 2026 / New
- Call for price
Exceed your expectations with the 2026 Yamaha SX250. With 400 horsepower, an innovative hull design, ample storage, and a functional layout, this boat is an unbeatable value. Key F... View Details

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2026 Yamaha 222S

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 22'
- 2026 / New
- Call for price
The 2026 Yamaha 222S, timeless style, premium performance. The 222S combines timeless styling, premium refinements, and class-leading performance in an affordable 22-foot package.... View Details

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2026 Yamaha 275SE

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 27'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha 275SE, elevaing boating luxury. Experience an exceptional blend of comfort, luxury, and distinctive design. Key Features Luxury and Performance - Step i... View Details

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2026 Yamaha AR220

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 22'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha AR220, value-packed watersports fun. Offering the perfect blend of value, versatility, and convenience in an affordable 22-foot package. Key Features Pe... View Details

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2026 Yamaha SX220

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 22'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha SX220, unmatched value, versatility, and affordability. With its roomy cockpit, abundant storage, and fuel-efficient dual engines, this boat offers exce... View Details

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Showing 43 to 63 of 1,625 boats found.

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