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  • Within 100 Miles Of
    Chicago, Illinois

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Boats for sale in Chicago Illinois

There are 758 new and used boats for sale in Chicago, Illinois. Browse Pontoon, Cruiser, Runabout, Fishing, Center Console, and Ski & Wake from brands like Sea Ray, Scout, Bayliner, Harris, Barletta, and Cruisers on BoatCrazy. View a wide selection of boats from $100 to $2,349,495.
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  • Boats
  • Within 100 Miles Of
    Chicago, Illinois
758 boats found within 100 miles out of 11,668 Boats Found
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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 AV32 Outboard

    2025 Aviara AV32 Outboard

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    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 Scout 261 XSS

    2025 Scout 261 XSS

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    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 Scout 175 Sportfish

    2025 Scout 175 Sportfish

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    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 215 XSF

    2025 Scout 215 XSF

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    Winthrop Harbor, IL

    Experience Luxury at Sea with the 2025 Scout 215 XSF Discover the ultimate blend of performance and elegance as you cruise the waters in style on this brand-new 2025 Scout 215 XSF.... View Details

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  • 2026 Sea Ray Sundancer 320 Outboard

    2026 Sea Ray Sundancer 320 Outboard

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 32'
    • 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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  • 2026 Saxdor 320 GTC

    2026 Saxdor 320 GTC

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 32'
    • 2026 / New
    • Call for price

    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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  • 2018 Crownline 264 CR

    2018 Crownline 264 CR

    $68,000
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 26'
    • 2018 / Used
    • $68,000

    Trailer Included! Priced to sell! Great opprotunity! Powered by a MerCruiser 6.2L MPI 300 HP V8 with a Bravo III dual-prop drive, the 264 CR delivers smooth handling, strong perfor... View Details

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    $68,000
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  • 2024 Aviara AV32

    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! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat f... View Details

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    $369,000
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  • 2027 Sea Ray SLX 280

    2027 Sea Ray SLX 280

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 28'
    • 2027 / New
    • Call for price

    Step up to confidence, comfort, and power with the 2027 Sea Ray SLX 280 (Stock #223209). Outfitted with a 430hp Mercury engine and luxury features throughout, this versatile 28-foo... View Details

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  • Price Drop 2002 Sea Ray 310 SUNDANCER

    2002 Sea Ray 310 SUNDANCER

    $44,900
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 33'
    • 2002 / Used
    • $44,900

    ***FRESH WATER!!!*** ***GENERATOR!!*** ***6.2L BRAVO 3 I/Os!!!*** Whether you're seeking your first sport cruiser or are an experienced operator, this is an opportunity to get on t... View Details

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    $44,900
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  • 2026 Scout 400 LXF Li-Ion

    2026 Scout 400 LXF Li-Ion

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    Winthrop Harbor, IL

    The 2026 Scout 400 LXF Li-Ion is a new model and alternative version to the current 400 LXF, complete with a lithium ion battery management system (no generator necessary). These b... View Details

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  • 2026 Scout 400 LXF

    2026 Scout 400 LXF

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    Winthrop Harbor, IL

    The revolutionary 2026 Scout 400 LXF, a true masterpiece of innovation in the world of boating. This stunning model combines exceptional technology, unmatched performance, and luxu... View Details

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  • 2026 Scout 425 LXF

    2026 Scout 425 LXF

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    Winthrop Harbor, IL

    The 425 LXF offers superior structural stability, strength and a Class-A finish creating unsurpassed performance. With a standard Seakeeper gyro stabilizer, second row seating, and... View Details

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  • 2026 Aquila 32 Sport

    2026 Aquila 32 Sport

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Catamaran
    • 32'
    • 2026 / New
    • Call for price

    Make everyday a weekend. The 2026 Aquila 32 Sport power catamaran answers the horizon's call with nimble performance and dayboating intelligence wrapped in a perfectly sized packag... View Details

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  • 2026 Scout 377 LXF

    2026 Scout 377 LXF

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    Winthrop Harbor, IL

    The 377 LXF is built as the ideal blend of performance, luxury and stylie. Loaded with Scout innovation, this model has a lithium ion bettery with battery management system (no gen... View Details

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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

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    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

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    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

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    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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Showing 43 to 63 of 758 boats found.
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