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Boats for sale in Chicago Illinois

There are 787 new and used boats for sale in Chicago, Illinois. Browse Pontoon, Cruiser, Runabout, Fishing, Center Console, and Bowrider from brands like Sea Ray, Scout, Bayliner, Harris, Starcraft, and Mastercraft on BoatCrazy. View a wide selection of boats from $100 to $2,199,495.
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  • Boats
  • Within 100 Miles Of
    Chicago, Illinois
787 boats found within 100 miles out of 11,634 Boats Found
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  • 2025 Yamaha Waverunner VX1050B-BB

    2025 Yamaha Waverunner VX1050B-BB

    $12,499
    La Porte, IN

    Discover the top-rated Yamaha WaveRunner VX Cruiser with Audio at Fays Marina. Enjoy top performance, durability, and innovation. Shop now for the best price and exclusive deals.... View Details

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    $12,499
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  • 2024 Yamaha Waverunner VX1050C-AA

    2024 Yamaha Waverunner VX1050C-AA

    $11,099
    La Porte, IN

    Experience the Yamaha Waverunner VX Cruiser 3-Person Watercraft in Deepwater Blue, at Fays Marina, La Porte, IN. MSRP $12,799 ON SALE $11,099 LAST ONE! SAVE $1,700 !!! through... View Details

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    $11,099
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  • Price Drop 2023 Viaggio DIAMANTE D 23S TRITOON

    2023 Viaggio DIAMANTE D 23S TRITOON

    $69,999
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 23'
    • 2023 / New
    • $69,999

    FAYS CLEAR THE DECKS FINAL CLEARANCE ON LUXURY TRI-TOON PONTOONS! New Viaggio Diamante D23S Tri Toon, Full Platinum Package, Power Bimini, Power Steering, BF250 hp Honda, More, Fa... View Details

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    $69,999
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  • 2026 Scout 175 Sportfish

    2026 Scout 175 Sportfish

    Call for price
    Winthrop Harbor, IL

    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

    2026 Saxdor 340 GTWA

    Call for price
    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

    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

    2025 Scout 277 Dorado

    Call for price
    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

    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 Sea Ray Sundancer 320 Outboard

    2026 Sea Ray Sundancer 320 Outboard

    Call for price
    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

    Call for price
    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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  • Price Drop 2018 Crownline 264 CR

    2018 Crownline 264 CR

    $52,000
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 26'
    • 2018 / Used
    • $52,000

    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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    $52,000
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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

    Call for price
    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

    Call for price
    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

    Call for price
    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

    Call for price
    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

    Call for price
    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

    Call for price
    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

    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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Showing 43 to 63 of 787 boats found.
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