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There are 2257 new and used boats for sale in Waukegan, Illinois. Browse Outboard Motors, Pontoon, Cruiser, Fishing, Center Console, and Runabout from brands like Scout, Mercury, Sea Ray, Yamaha, Harris, and Honda on BoatCrazy. View a wide selection of boats from $300 to $3,890,000.
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  • Boats
  • Within 100 Miles Of
    Waukegan, Illinois
2,257 boats found within 100 miles from Waukegan, Illinois
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  • 2001 Regal Commodore 2660

    2001 Regal Commodore 2660

    $36,900
    Saint Joseph, MI

    Tandem Axle Trailer included! Twin Volvo V-6's. Luxurious, sporty and spacious, this Regal 2660 Commodore also features the option of trailering to your summer destinations! The co... View Details

    View 49 Photos and Details Contact Seller
    $36,900
    VIEW DETAILS
  • 2026 Chaparral 23 SSi

    2026 Chaparral 23 SSi

    $89,259
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 23' / 8'
    • 2026 / New
    • $89,259

    Everything that has made Chaparral's wildly popular SSi Series the talk of the waterways, gets bigger and better with the amazing 23 SSi. With a ChaparralONE price including the tr... View Details

    View 44 Photos and Details Contact Seller
    $89,259
    VIEW DETAILS
  • 2026 Chaparral 21 SSi OB

    2026 Chaparral 21 SSi OB

    $75,794
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 21' / 8'
    • 2026 / New
    • $75,794

    Now on display, see this new 2026 Chaparral 21 SSi powered by a hearty 200 HP Yamaha 4-stroke outboard. Chaparral's innovative use of space means an abundance of cockpit space, sto... View Details

    View 26 Photos and Details Contact Seller
    $75,794
    VIEW DETAILS
  • 2026 Chaparral SSX 4

    2026 Chaparral SSX 4

    Call for price
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 24' / 8'
    • 2026 / New
    • Call for price

    The SSX 4 packs more elegance, performance, and innovation than boaters have ever experienced at this widely popular length. Its stylish lines, meticulous attention to detail, and... View Details

    View 38 Photos and Details Contact Seller
    Call for price
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  • 2026 Chaparral SSX 6

    2026 Chaparral SSX 6

    Call for price
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 26' / 8'
    • 2026 / New
    • Call for price

    Look no further-the SSX 6 is breaking barriers and setting the standard for on-water comfort and performance. Equipped with a state-of-the-art oversized touchscreen display, the he... View Details

    View 44 Photos and Details Contact Seller
    Call for price
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  • 2017 Chaparral 21 H2O Ski & Fish

    2017 Chaparral 21 H2O Ski & Fish

    $34,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Fish & Ski
    • 21' / 8'
    • 2017 / Used
    • $34,900

    Sold new @ Pier 33 in 2017 this boat has lived on its factory trailer and has been garaged since its purchase! With very low freshwater only hours on the motor this little runabout... View Details

    View 21 Photos and Details Contact Seller
    $34,900
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  • 2003 Chaparral 260 SSi

    2003 Chaparral 260 SSi

    $34,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 27' / 0'
    • 2003 / Used
    • $34,900

    In our showroom now! If you are looking for a great value in today's boating market this is it! This lovingly cared for 260 SSi has only 543 freshwater hours on the Mercruiser 496... View Details

    View 30 Photos and Details Contact Seller
    $34,900
    VIEW DETAILS
  • 2016 Chaparral 287 SSX

    2016 Chaparral 287 SSX

    $74,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 28' / 0'
    • 2016 / Used
    • $74,900

    See this sharp, spacious fun machine, ready to take you to your favorite destinations. This 9-foot beam bow rider offers an abundance of comfortable passenger seating with a double... View Details

    View 42 Photos and Details Contact Seller
    $74,900
    VIEW DETAILS
  • 2018 Lund LX220 Pontoon

    2018 Lund LX220 Pontoon

    $39,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Pontoon
    • 23' / 0'
    • 2018 / Used
    • $39,900

    Meet your ticket to endless summer fun on this 2018 Lund LX220 Tritoon. This Lund brings the perfect blend of power, comfort, and pure on-the-water fun. Powered by a 200HP Mercury... View Details

    View 46 Photos and Details Contact Seller
    $39,900
    VIEW DETAILS
  • Price Drop 1996 Cruisers 3375 Rogue

    1996 Cruisers 3375 Rogue

    $40,000
    Saint Joseph, MI

    Stock #457168 Reason for selling is "Bought another boat". ANY and ALL offers will be put in front of our seller! Submit your offer today! Two Berths, Slip and Storage Prepaid t... View Details

    View 10 Photos and Details Contact Seller
    $40,000
    VIEW DETAILS
  • Price Drop 2014 Chaparral 287 SSX

    2014 Chaparral 287 SSX

    $74,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 28' / 9'
    • 2014 / Used
    • $74,900

    Sharp, powerful Chaparral 287 SSX. Includes Volvo Penta 430 HP V-8 with DTS. Just 260 engine hours. Don’t miss out on this nicely maintained Chaparral 287 SSX. This 9-foot beam bo... View Details

    View 31 Photos and Details Contact Seller
    $74,900
    VIEW DETAILS
  • Price Drop 2021 Chaparral 307 SSX

    2021 Chaparral 307 SSX

    $149,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 30' / 9'
    • 2021 / Used
    • $149,900

    One-Owner, Fresh-Water, rack-stored Chaparral 307 SSX. Plushness and Performance! Loaded with all of Chaparral's best features, with an abundance of passenger space, the 307 SSX is... View Details

    View 39 Photos and Details Contact Seller
    $149,900
    VIEW DETAILS
  • 2024 Cobalt R8 Outboard

    2024 Cobalt R8 Outboard

    $219,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 27' / 8'
    • 2024 / Used
    • $219,900

    See This stunning 2024 Cobalt R8 Outboard, a remarkable bowrider that combines elegance with performance. Measuring an impressive 27.83 feet in overall length, this vessel is craft... View Details

    View 48 Photos and Details Contact Seller
    $219,900
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  • 2007 Chaparral 350 Signature

    2007 Chaparral 350 Signature

    $129,500
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 37' / 11'
    • 2007 / Used
    • $129,500

    Always fresh-water, loaded with features. Twin Merc 8.1L 370 HP inboards with 460 hours. This is an ideal opportunity to own a well-cared-for Chaparral 350 Signature featuring a pr... View Details

    View 35 Photos and Details Contact Seller
    $129,500
    VIEW DETAILS
  • 2005 Formula 260 Bowrider

    2005 Formula 260 Bowrider

    $46,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Runabout
    • 26' / 8'
    • 2005 / Used
    • $46,900

    Chase sunsets with this 2005 Formula 260 Bowrider, a premium sport boat built for performance, comfort, and luxury. A top brand known for its superior handling, quality constructio... View Details

    View 31 Photos and Details Contact Seller
    $46,900
    VIEW DETAILS
  • 2018 Chaparral Vortex 203 VRX

    2018 Chaparral Vortex 203 VRX

    $35,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Jet boat
    • 20' / 8'
    • 2018 / Used
    • $35,900

    The 203 VRX features the hull design, interior layout and high quality construction Chaparral is known for. In addition to the head-turning style, the VRX includes a black folding... View Details

    View 42 Photos and Details Contact Seller
    $35,900
    VIEW DETAILS
  • 2000 Crownline 290 CR

    2000 Crownline 290 CR

    $34,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 31' / 10'
    • 2000 / Used
    • $34,900

    This Crownline 290 CR is a spacious small express cruiser powered by twin Mercruiser 5.7 EFI's and NEW Bravo III drives! She has about 700 hours on her hour meters and appears to h... View Details

    View 30 Photos and Details Contact Seller
    $34,900
    VIEW DETAILS
  • Price Drop 2021 Qwest LS 822 DS Bar

    2021 Qwest LS 822 DS Bar

    $49,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Pontoon
    • 22' / 8'
    • 2021 / Used
    • $49,900

    This 2021 Qwest LS 822 perfectly blends style and performance with great fishing capabilites. Power by a 200HP Honda and Upgraded tiple toon package and aluminum underskining makes... View Details

    View 34 Photos and Details Contact Seller
    $49,900
    VIEW DETAILS
  • Price Drop 2017 Chaparral 330 Signature

    2017 Chaparral 330 Signature

    $194,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 33' / 10'
    • 2017 / Used
    • $194,900

    Now available, see this 2017 Chaparral 330 Signature. Always fresh-water, with just 243 engine hours. Designed for summer adventures and weekend getaways, the Chaparral 330 Signatu... View Details

    View 51 Photos and Details Contact Seller
    $194,900
    VIEW DETAILS
  • Price Drop 2016 Chaparral 307 SSX

    2016 Chaparral 307 SSX

    $129,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 30' / 9'
    • 2016 / Used
    • $129,900

    Meet your next on-the-water obsession: the 2016 Chaparral 307 SSX  a head turning mix of luxury, performance, and pure boating bliss! At 30 feet, she delivers a ride as smooth as s... View Details

    View 48 Photos and Details Contact Seller
    $129,900
    VIEW DETAILS
  • Price Drop 2000 Chaparral Signature 300

    2000 Chaparral Signature 300

    $37,500
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 29' / 10'
    • 2000 / Used
    • $37,500

    If you are looking for a small family cruiser with all the amenities you just found it! This Chaparral Signature 300 has all the creature comforts including Air Conditioning, Fusio... View Details

    View 31 Photos and Details Contact Seller
    $37,500
    VIEW DETAILS
Showing 1681 to 1701 of 2,257 boats found.
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