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Boats for sale in Chicago Illinois

There are 733 new and used boats for sale in Chicago, Illinois. Browse Cruiser, Pontoon, Runabout, Fishing, Center Console, and Ski & Wake from brands like Sea Ray, Scout, Harris, Bayliner, Cruisers, and Mastercraft 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
733 boats found within 100 miles out of 11,595 Boats Found
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  • 2026 Sea Ray SDX 290

    2026 Sea Ray SDX 290

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    Antioch, IL
    • Antioch, IL
    • Runabout
    • 29'
    • 2026 / New
    • Call for price

    Built for fun, introducing the 2026 Sea Ray SDX 290. When an active family loves water sports, they generall want to share their good times with friends. That's where the SDX 290 c... View Details

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  • 2026 Sea Ray SPX 210 Outboard

    2026 Sea Ray SPX 210 Outboard

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    Antioch, IL
    • Antioch, IL
    • Runabout
    • 24'
    • 2026 / New
    • Call for price

    Performance and fun. The reimagined 2026 Sea Ray SPX 210 Outboard is designed to be noticed, and delivers the next level of fun, perfect for hosting friends, sharing a casual cruis... View Details

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  • 2026 Sea Ray SPX 230 Outboard

    2026 Sea Ray SPX 230 Outboard

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    Antioch, IL
    • Antioch, IL
    • Runabout
    • 26'
    • 2026 / New
    • Call for price

    Powerful performance, agile handling. The 2026 Sea Ray SPX 230 Outboard is built to thrill. It combines the powerful performance and agile handling you'd expect from a world-class... View Details

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  • 2026 Mastercraft XT20

    2026 Mastercraft XT20

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    Antioch, IL
    • Antioch, IL
    • Ski & Wake
    • 20'
    • 2026 / New
    • Call for price

    Introducing the 2026 Mastercraft XT20. At 20 feet, the XT20 is compact and garage-friendly-but still delivers everything you'd expect from a MasterCraft: SurfStar performance, prem... View Details

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  • 2026 Mastercraft XT22 T

    2026 Mastercraft XT22 T

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    Antioch, IL
    • Antioch, IL
    • Ski & Wake
    • 22'
    • 2026 / New
    • Call for price

    Introducing the 2026 MasterCraft XT22 T, pairing iconic style with modern muscle, delivering proven performance in a package that looks as good as it rides. With a traditional bow... View Details

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  • 2026 Mastercraft XT22

    2026 Mastercraft XT22

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    Antioch, IL
    • Antioch, IL
    • Ski & Wake
    • 22'
    • 2026 / New
    • Call for price

    Introducing the 2026 MasterCraft XT22-all about great waves, plenty of room, and style that fits your vibe. At 22 feet, it holds up to 16 people and comes with smart features like... View Details

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  • 2026 Mastercraft X24

    2026 Mastercraft X24

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    Antioch, IL
    • Antioch, IL
    • Ski & Wake
    • 24'
    • 2026 / New
    • Call for price

    The Mastercraft X24: Experience the epitome of adrenaline-fueled excitement and aquatic thrills with the Mastercraft X24. A powerhouse vessel designed to create unforgettable momen... View Details

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  • 2026 Sailfish 316 DC

    2026 Sailfish 316 DC

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    Antioch, IL
    • Antioch, IL
    • Runabout
    • 33'
    • 2026 / New
    • Call for price

    The new 316 dual console is a versatile family fishing boat that checks all the boxes: comfort, safety, quality and reliability. Well-equipped for a range of activities, the 316 DC... View Details

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  • 2026 Sailfish 242 CC

    2026 Sailfish 242 CC

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    Antioch, IL

    Designed and built for offshore anglers, the 242 center console features the Sailfish VDS hull, ensuring smooth, powerful performance. With its larger console headspace, ample seat... View Details

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  • 2026 Sailfish 276 DC

    2026 Sailfish 276 DC

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    Antioch, IL
    • Antioch, IL
    • Runabout
    • 29'
    • 2026 / New
    • Call for price

    Incredible versatility and comfort are hallmarks of the 276 dual console. A 6th-generation VDS hull ensures a soft, dry ride, while the spacious, ergonomic deck design and an array... View Details

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  • 2026 Sailfish 312 CC

    2026 Sailfish 312 CC

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    Antioch, IL

    The all-new 2026 Sailfish center console offers an incredible VDS hull design for fuel efficiency and comfort, a striking appearance, ample space, and prioritized safety. It has ev... View Details

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  • 2026 Sailfish 245 DC

    2026 Sailfish 245 DC

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    Antioch, IL
    • Antioch, IL
    • Runabout
    • 24'
    • 2026 / New
    • Call for price

    With comfortable seating for 12, a spacious step-down head and an optiona cockpit galley, the 245 dual console is designed for active families as well as serious offshore anglers.... View Details

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  • 2026 Sailfish 241 CC

    2026 Sailfish 241 CC

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    Antioch, IL

    With its sleek, dynamic profile and 6th generation VDS hull, combined with a highly functional layout and long-lasting Sailtech Construction, the 241 center console is a powerful f... View Details

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  • 2026 Sailfish 360 CC

    2026 Sailfish 360 CC

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    Antioch, IL

    The flagship 360 center console combines unsurpassed quality and state-of-the-art technology with a layout and features designed for maximum versatility. Fish, play, cruise or ente... View Details

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  • 1981 Sylvan Sea monster

    1981 Sylvan Sea monster

    $2,500
    Sycamore, IL

    Sylvan Sea Monster - A Classic Choice for Adventurous Spirits Step aboard the Sylvan Sea Monster, a vessel that embodies the robust craftsmanship of the early 1980s. Perfect for t... View Details

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    $2,500
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  • 1996 Bayliner Ciera 2655

    1996 Bayliner Ciera 2655

    $21,250
    Wilmington, IL

    Stock #304401 Reason for selling is "Downsizing". ANY and ALL offers will be put in front of our seller! Submit your offer today! Very Clean Ciera 2655 Sunbridge .Full enclosure... View Details

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    $21,250
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  • Price Drop 2022 Coach 243 RFC 3-SERIES TRITOON

    2022 Coach 243 RFC 3-SERIES TRITOON

    $53,990
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 25'
    • 2022 / New
    • $53,990

    FAYS CLEAR THE DECKS FINAL CLEARANCE ON LUXURY TRI-TOON PONTOONS! MSRP -- $104,168 CLEAR THE DECKS FOR NEW MODELS SALE -- $53,990 + frt & prep - WHY BUY USED WHEN YOU CAN BUY NE... View Details

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    $53,990
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  • Price Drop 1979 Imperial V 171 BOWRIDER O/B

    1979 Imperial V 171 BOWRIDER O/B

    $500
    La Porte, IN
    • La Porte, IN
    • Cruiser
    • 18'
    • 1979 / Used
    • $500

    Revitalize your passion for marine restoration with this 1979 Imperial V171 Bowrider with 115hp Power Trim Evinrude and Shorelandr trailer, available at Fays Marina La Porte Indian... View Details

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    $500
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  • Price Drop 1994 Other WILDTHING INFLATABLE

    1994 Other WILDTHING INFLATABLE

    $475
    La Porte, IN

    Used 1994 Wildthing Rigid Inflatable Boat (RIB/WAHOO) by P.S. Marine. Lightweight, fast, stable, and ideal for utility, tender, or sport use. For sale at Fay’s Marina, La Porte, IN... View Details

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    $475
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  • Price Drop 1986 Stingray SVC 207 SS CUDDY 5.7L 260 HP V8 TANDEM TRL

    1986 Stingray SVC 207 SS CUDDY 5.7L 260 HP V8 TANDEM TRL

    $975
    La Porte, IN
    • La Porte, IN
    • Deck Boat
    • 20'
    • 1986 / Used
    • $975

    Revitalize your passion for marine restoration with this 1986 Stingray SVC 207 Cuddy Cabin Cruiser with V8 Mercruiser and Trailer available at Fays Marina La Porte Indiana. Your b... View Details

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    $975
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  • Price Drop 1997 Bayliner 2355 CIERA SUNBRIDGE 5.7L MCM Yard Trl

    1997 Bayliner 2355 CIERA SUNBRIDGE 5.7L MCM Yard Trl

    $6,999
    La Porte, IN
    • La Porte, IN
    • Cruiser
    • 23'
    • 1997 / Used
    • $6,999

    1997 Bayliner 2355 Ciera Sunbridge with 5.7L MerCruiser, shorepower, fresh bottom paint, cabin amenities, and free trailer (needs springs/tires). For sale at Fay’s Marina. Bayline... View Details

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    $6,999
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Showing 274 to 294 of 733 boats found.
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