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Boats for sale in Chicago Illinois

There are 790 new and used boats for sale in Chicago, Illinois. Browse Pontoon, Cruiser, Fishing, Runabout, Center Console, and Ski & Wake from brands like Sea Ray, Scout, Harris, Bayliner, Barletta, and Mastercraft on BoatCrazy. View a wide selection of boats from $100 to $2,499,495.
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  • Boats
  • Within 100 Miles Of
    Chicago, Illinois
790 boats found within 100 miles from Chicago, Illinois
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  • 2025 Scout 175 Sportfish

    2025 Scout 175 Sportfish

    Call for price
    Winthrop Harbor, IL

    Experience Luxury with the 2025 Scout 175 Sportfish Performance RedefinedStep aboard the 2025 Scout 175 Sportfish for an unforgettable experience on the water. Powered by a Mercury... View Details

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  • 2025 Scout 261 XSS

    2025 Scout 261 XSS

    Call for price
    Winthrop Harbor, IL

    Experience Luxury on the Water with the 2025 Scout 261 XSS Step aboard the 2025 Scout 261 XSS and embrace a world of luxury and adventure. This new vessel from Scout promises unpar... View Details

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  • 2025 Aviara AV32 Outboard

    2025 Aviara AV32 Outboard

    Call for price
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Bowrider
    • 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

    2025 Aviara AV36

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Bowrider
    • 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

    2025 Aviara AV40 Outboard

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Bowrider
    • 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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  • 2016 Regal 2100 SURF

    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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  • 2026 Aquila 28 Molokai Cuddy

    2026 Aquila 28 Molokai Cuddy

    Call for price
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Pilothouse
    • 31'
    • 2026 / New
    • Call for price

    Born from the Pacific. Built for wherever "Out There" takes you. All-weather protection. Offshore performance. Profession capability. The 2026 Aquila 28 Molokai Cuddy merges intell... View Details

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  • 2026 Aquila 28 Molokai

    2026 Aquila 28 Molokai

    Call for price
    Winthrop Harbor, IL

    Born from the Pacific. Built for wherever "Out There" takes you. The Aquila 28 Molokai merges professional-grade fishing capability with practical versatility, extending your horiz... View Details

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  • 2026 Aquila 47 Molokai

    2026 Aquila 47 Molokai

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    Winthrop Harbor, IL

    Some chase fish. Others chase freedom. With the Aquila 47 Molokai power catamaran, you don't have to choose. The 2026 Aquila 47 Molokai is the first catamaran of its kind. Until no... View Details

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  • 2026 Galeon 440 FLY

    2026 Galeon 440 FLY

    Call for price
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Yacht
    • 46'
    • 2026 / New
    • Call for price

    Galeon has leverage all of its storied boatbuilding experience to create the 440 FLY, a medium-sized motoryacht packed with intelligent innovations and a fresh approach to onboard... View Details

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  • 2026 Scout 357 LXF

    2026 Scout 357 LXF

    Call for price
    Winthrop Harbor, IL

    The 357 LXF S-Class will surpass all of your expectations. When you step abpard and experience the extended space designed into this model, coupled with the performance, innovation... View Details

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  • 2026 Galeon 425 HTS

    2026 Galeon 425 HTS

    Call for price
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Yacht
    • 44'
    • 2026 / New
    • Call for price

    The 2026 Galeon 425 HTS is a 44-foot, classic express-style cruiser with options usually seen on much larger vessels. Specificall, the salon and cockpit can convert into a single,... View Details

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  • 2026 Galeon 470 SKY

    2026 Galeon 470 SKY

    Call for price
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Yacht
    • 47'
    • 2026 / New
    • Call for price

    The Galeon 470 SKY is a versatile cruiser that handles with grace and verve. She features a top deck with incredible viwes and a helm station will impress any captain. This cessel... View Details

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  • 2026 Galeon 375 GTO

    2026 Galeon 375 GTO

    Call for price
    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 Galeon 435 GTO

    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 Galeon 410 HTC

    2026 Galeon 410 HTC

    Call for price
    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 Aquila 36 Sport

    2026 Aquila 36 Sport

    Call for price
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Catamaran
    • 36'
    • 2026 / New
    • Call for price

    Make everyday a weekend. The award-winning Aquila 36 Sport power catamaran empowers those who see perfect weather as a call to action, delivering an exhilarating platform for spont... View Details

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  • 2026 Galeon 450 HTC

    2026 Galeon 450 HTC

    Call for price
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Yacht
    • 46'
    • 2026 / New
    • Call for price

    Created for those who are active on the water, the Galeon 450 HTC includes all the essentials for fun and more. This stunning 45'8" state-of-the-art model, crafted in collaboration... View Details

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  • 2026 Aquila 42 Yacht

    2026 Aquila 42 Yacht

    Call for price
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Catamaran
    • 42'
    • 2026 / New
    • Call for price

    This is the life the award-winning Aquila 42 Yacht power catamaran is made forL accessible luxury, effortless entertaining, and those special moments when intelligent design transf... View Details

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  • 2006 Regal 3860

    2006 Regal 3860

    $187,488
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 38'
    • 2006 / Used
    • $187,488

    Experience the Luxury of the 2006 Regal 3860 Embark on endless adventures with the 2006 Regal 3860, a stunning vessel that perfectly balances cutting-edge performance and timeless... View Details

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    $187,488
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  • 2024 Sea Ray 310 SLX

    2024 Sea Ray 310 SLX

    $299,900
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 31'
    • 2024 / Used
    • $299,900

    2024 Sea Ray 310 SLX Experience the thrill of the open water with the 2024 Sea Ray 310 SLX, a harmonious blend of power and elegance. This luxury vessel is powered by two MERCRUISE... View Details

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    $299,900
    VIEW DETAILS
Showing 43 to 63 of 790 boats found.
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