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Available Boats for sale in Chicago Illinois

  • Act fast on this limited-time offer! Discover Unmatched Luxury on Water Experience the epitome of aquatic elegance with the 2026 Starcraft SLS-3 Q DH. This stunning vessel combines... View Details

    $90,076
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  • THIS 2026 STARCRAFT EXS 3 R DH IS POWERED BY A HONDA 250HP WITH iST CONTROLS AND SHOW WITH THE FOLLOWING OPTIONS. FULL TEAK WEAVE FLOORING, WET SOUDS RADIO WREAR SPACING SPEAKERS,... View Details

    $91,073
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  • Is the Cabrio right for you? Spend time with family on the water in the price concious Cabrio. The same fit and finish, innovation, performance and superior construction that Barle... View Details

    $93,049
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  • Act fast on this limited-time offer! 2026 Barletta CABRIO22U Experience the allure of waterfront living with the stunning 2026 Barletta CABRIO22U, available exclusively at SkipperB... View Details

    $94,783
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  • If you are looking for a sporty, great performing, hot looking express cruiser, look no further! This Formula 330 Sun Sport is the perfect fit for your family's summer fun! Nicely... View Details

    $94,900
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  • Act fast on this limited-time offer! 2026 Barletta CABRIO22U Experience the allure of luxury on the water with the stunning 2026 Barletta CABRIO22U. This new vessel promises unmatc... View Details

    $95,773
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  • In Stock Now See the Chaparral 23 SSi, our best-selling 23-footer! This 23 SSi is superbly equipped with Mercury 300 HP Bravo 3 MPI power and many Chaparral extras. Trailer include... View Details

    $96,864
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  • Act fast on this limited-time offer! 2026 Barletta CABRIO22M Experience the height of luxury and performance with the 2026 Barletta CABRIO22M, now available at SkipperBud's Pewauke... View Details

    $97,116
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  • Is the Cabrio right for you/ Spend time with family on the water in the price sonscious Cabrio. The same fit and finish, innovation, performance adn superior construction that Barl... View Details

    $97,333
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  • Act fast on this limited-time offer! Discover Elegance on Water Experience the allure of luxury boating with the 2026 Barletta CABRIO24UE, where sophistication meets adventure. Cra... View Details

    $97,800
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  • Act fast on this limited-time offer! 2026 Harris 250SL - Luxury Awaits Experience the elegance and exhilaration of the open water with the 2026 Harris 250SL. This stunning vessel b... View Details

    $99,145
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  • 2022 Barletta 25 U TT View Details

    $99,995
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  • Act fast on this limited-time offer! Introducing the 2026 Barletta CABRIO24UE Experience unparalleled luxury on the water with the stunning 2026 Barletta CABRIO24UE. Designed with... View Details

    $99,995
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  • Price Drop 2026 Sylvan L5 RLZ

    Act fast on this limited-time offer! The Sylvan L5 RLZ pontoon epitomizes the essence of a family-friendly pontoon, featuring two convenient flip-back rear lounges that flip for fo... View Details

    $101,822
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  • 2026 Barletta CABRIO24QC Experience the epitome of aquatic luxury with the 2026 Barletta CABRIO24QC, now available at SkipperBud's Pewaukee in Pewaukee, WI. This stunning vessel re... View Details

    $102,637
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  • Act fast on this limited-time offer! Experience the Ultimate Luxury on Water Step aboard the 2026 Yamaha 252S, where unparalleled performance meets exquisite craftsmanship. This ne... View Details

    $104,740
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  • Price Drop 2002 Regal 3860

    Stock #467673 Reason for selling is "New Adventure!". This Regal has been on the market for more than 30 days (May 1st). If you are thinking of making an offer, submit it today a... View Details

    $104,999
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  • Act fast on this limited-time offer! Experience Unmatched Luxury Introducing the stunning 2026 Barletta CABRIO24U, where elegance meets adventure. This new vessel is designed for t... View Details

    $105,187
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  • Act fast on this limited-time offer! Experience Unmatched Luxury Introducing the stunning 2026 Harris 230SOL, a masterpiece that blends elegance and performance seamlessly. This ne... View Details

    $105,502
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  • Price Drop 2025 Mastercraft NXT20

    Contact us to find out ALL available savings! Explore the Waves in Style with the NXT20 Discover the perfect combination of affordability and excitement with the NXT20 boat. Measur... View Details

    $105,795
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  • Step into world-class waterskiing performance with this very gently used 2023 Malibu Response TXi, complete with a matching trailer. Known as the pinnacle of precision in the water... View Details

    $105,990
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Showing 295 to 315 of 1,217 boats found.