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Boats for sale in Chicago Illinois

There are 1736 new and used boats for sale in Chicago, Illinois. Browse Outboard Motors, Pontoon, Fishing, Center Console, Cruiser, and Runabout from brands like Mercury, Scout, Honda, Sea Ray, Yamaha, and Harris on BoatCrazy. View a wide selection of boats from $300 to $849,900.
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  • Boats
  • Within 100 Miles Of
    Chicago, Illinois
1,736 boats found within 100 miles from Chicago, Illinois
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  • 2025 Scout 231 XSB

    2025 Scout 231 XSB

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    Winthrop Harbor, IL

    Introducing the 231 XSB - The Ultimate Fishing Machine The 231 XSB is the latest addition to our bay boat/inshore lineup, designed to take your fishing experience to the next level... View Details

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  • 2025 Bayliner M19

    2025 Bayliner M19

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Runabout
    • 18' / 0'
    • 2025 / New
    • Call for price

    The 2025 Bayliner M19, a true masterpiece of engineering and design. This versatile bowrider is perfect for those seeking endless thrills on the water. Crafted with precision and e... View Details

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  • 2025 Bayliner M15

    2025 Bayliner M15

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Runabout
    • 15' / 0'
    • 2025 / New
    • Call for price

    Introducing the stunning and highly versatile 2025 Bayliner M15! Crafted to perfection, this compact bowrider boat is perfect for both beginners and experienced boaters alike. With... View Details

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  • 2025 Tige Z5

    2025 Tige Z5

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Ski & Wake
    • 0' / 0'
    • 2025 / New
    • Call for price

    Introducing the 2025 Tige Z5 - Luxury Redefined Prepare to elevate your boating experience with the stunning 2025 Tige Z5, a masterpiece of performance and luxury. Unleash Power an... View Details

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  • 2025 Bayliner T24CC

    2025 Bayliner T24CC

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    Winthrop Harbor, IL

    Introducing the latest game-changer in our Trophy series, the T24CC. This innovative center console boat takes performance and capabilities to new heights, offering an array of exc... View Details

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  • 2026 Aquila 28 Molokai Cuddy

    2026 Aquila 28 Molokai Cuddy

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Pilothouse
    • 31' / 0'
    • 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 Cruisers 46 Cantius

    2026 Cruisers 46 Cantius

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 47' / 0'
    • 2026 / New
    • Call for price

    Step aboard the pinnacle of maritime luxury where tranquility and timelessness converge seamlessly. From the expansive master suite to the gorgeous VIP stateroom, every corner of t... View Details

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  • 2026 Scout 261 XSS

    2026 Scout 261 XSS

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    Winthrop Harbor, IL

    The 261 XSS is an inshore/offshore crossover and is loaded with notable features such as the large casting fore and rear deck; port and starboard aerated baitwells; ample rod stora... View Details

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  • 2026 Galeon 400 FLY

    2026 Galeon 400 FLY

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Yacht
    • 41' / 0'
    • 2026 / New
    • Call for price

    The 2026 Galeon 400 FLY provides unrivaled entertainment space for a yacht in its class. Innovative side balconies on either side of the cockpit fold out to create massive amounts... View Details

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  • 2026 Sea Ray SDX 250 Outboard

    2026 Sea Ray SDX 250 Outboard

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Runabout
    • 28' / 0'
    • 2026 / New
    • Call for price

    True leisure and maximum comfort. The 2026 Sea Ray SDX 250 Outboard is built for true leisure and comfort. With exceptional storage space, enhanced ergonomic seating, and dual 9" d... View Details

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  • 2026 Sea Ray SLX 400 Outboard

    2026 Sea Ray SLX 400 Outboard

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 42' / 0'
    • 2026 / New
    • Call for price

    Orchestrated excellence. The 2026 Sea Ray's SLX 400 Outboard, "The Entertainer", is an outboard variant of the Innovation Award-winning SLX 400, with massive capacity, deluxe ameni... View Details

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  • 2026 Sea Ray SLX 350 Outboard

    2026 Sea Ray SLX 350 Outboard

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 38' / 0'
    • 2026 / New
    • Call for price

    Introducing the 2026 Sea Ray SLX 350 Outboard, luxury elevated. The SLX 350 Outboard incorporates top SLX features and enhancements that set the standard for large dayboats. The SL... View Details

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  • 2026 Sea Ray SLX 310 Outboard

    2026 Sea Ray SLX 310 Outboard

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 34' / 0'
    • 2026 / New
    • Call for price

    Share the thrill. Expansive social areas, a standard wet bar and plenty of available seating means hosting friends and family has been more comfortable. Aboard the 2026 Sea Ray SLX... View Details

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  • 2026 Sea Ray SLX 350

    2026 Sea Ray SLX 350

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Runabout
    • 36' / 0'
    • 2026 / New
    • Call for price

    Luxury elevated. Sea Ray's SLX 350 hosts an array of features designed for an excellent on-water experience and optimal performance. Powered by twin Mercury MerCruiser 6.2L engines... View Details

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  • 2026 Sea Ray SLX 280

    2026 Sea Ray SLX 280

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 29' / 0'
    • 2026 / New
    • Call for price

    Head turning elegance. Make your ultimate getaway in the 2026 Sea Ray SLX 280. Excluding luxury in a single glance, the elegant vessel showcases peak performance, impeccable style... View Details

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  • 2026 Sea Ray SLX 400

    2026 Sea Ray SLX 400

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 40' / 0'
    • 2026 / New
    • Call for price

    Adventure awaits with the 2026 Sea Ray SLX 400. Winner of an NMMA Innovation Award, Sea Ray's SLX 400, the "The Entertainer", combines peak performance, superior comfort, incredibl... View Details

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  • 2026 Sea Ray SLX 280 Outboard

    2026 Sea Ray SLX 280 Outboard

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 31' / 0'
    • 2026 / New
    • Call for price

    Introducing the 2026 Sea Ray SLX 280 Outboard. Experience luxury and performance like never before with the Sea Ray SLX 280 Outboard. This stylish and modern boat is designed to el... View Details

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  • 2026 Sea Ray SPX 190 Outboard

    2026 Sea Ray SPX 190 Outboard

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Runabout
    • 22' / 0'
    • 2026 / New
    • Call for price

    The ultimate in fun. Discover the water like never before with the 2026 Sea Ray SPX 190 Outboard. Combining sleek aesthetics with advanced technology, this model redefins the moder... View Details

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  • 2026 Sea Ray SDX 270 Surf

    2026 Sea Ray SDX 270 Surf

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Runabout
    • 27' / 0'
    • 2026 / New
    • Call for price

    Elegant design and superior performance. The SDX 270 Surf belongs in a class all its own With the capability to pursue full-day adventures, this exquisite surf-ready model takes fu... View Details

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  • 2026 Sea Ray SDX 270 Outboard

    2026 Sea Ray SDX 270 Outboard

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Runabout
    • 30' / 0'
    • 2026 / New
    • Call for price

    Introducing the 2026 Sea Ray SDX 270 Outboard. Outboard power and Sea Ray style. Category-leadign space, plush seating and Sea Ray's legendary attention to detail make the SDX 270... View Details

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  • 2026 Sea Ray SPX 190

    2026 Sea Ray SPX 190

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    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Runabout
    • 20' / 0'
    • 2026 / New
    • Call for price

    Your companion for endless fun. Discover the epitome of sporty sophistication with the new 2026 Sea Ray SPX 190. Designed to deliver exhilarating thrills and timeless style, this a... View Details

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Showing 211 to 231 of 1,736 boats found.
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