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Boats for sale in Chicago Illinois

There are 1172 new and used boats for sale in Chicago, Illinois. Browse Cruiser, Runabout, Pontoon, Fishing, Ski & Wake, and Center Console from brands like Sea Ray, Scout, Harris, Mastercraft, Cruisers, and Bayliner on BoatCrazy. View a wide selection of boats from $300 to $3,395,000.
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  • Boats
  • Within 100 Miles Of
    Chicago, Illinois
1,172 boats found within 100 miles out of 14,803 Boats Found
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  • 2026 Sea Ray SLX 280 Outboard

    2026 Sea Ray SLX 280 Outboard

    Call for price
    Walworth, WI
    • Walworth, WI
    • 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

    View 30 Photos and Details Contact Seller
    Call for price
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  • 2026 Sea Ray SLX 350

    2026 Sea Ray SLX 350

    Call for price
    Walworth, WI
    • Walworth, WI
    • 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

    View 13 Photos and Details Contact Seller
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  • 2002 Regal Commodore 3860

    2002 Regal Commodore 3860

    $114,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 40' / 13'
    • 2002 / Used
    • $114,900

    Introducing the Regal Commodore 3860, a stunning cruiser that promises an exceptional boating experience. With an overall length of 40 feet, this vessel boasts a sleek design, ensu... View Details

    View 50 Photos and Details Contact Seller
    $114,900
    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
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  • 2024 Yamaha 252SE

    2024 Yamaha 252SE

    $84,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Jet boat
    • 24' / 8'
    • 2024 / Used
    • $84,900

    Check out this 2024 Yamaha Boats 252SE, a remarkable jet boat that combines performance and style. Powered by twin Yamaha 1.9L High Output inboard engines, each delivering an impre... View Details

    View 47 Photos and Details Contact Seller
    $84,900
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  • 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
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  • 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
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  • 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
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  • 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
  • 2018 Chaparral 191 Suncoast

    2018 Chaparral 191 Suncoast

    $37,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 20' / 8'
    • 2018 / Used
    • $37,900

    The 191 Suncoast breaks down boating to its basics, while not sacrificing the Chaparral design, style, and quality you have come to expect. A large open concept seating arrangement... View Details

    View 31 Photos and Details Contact Seller
    $37,900
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  • Price Drop 2016 Chaparral 307 SSX

    2016 Chaparral 307 SSX

    $134,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 30' / 9'
    • 2016 / Used
    • $134,900

    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
    $134,900
    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
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  • Price Drop 1977 Trojan F30 Express

    1977 Trojan F30 Express

    $10,900
    Saint Joseph, MI

    NEW PRICE!! MAKE OFFER!! This classically-styled Trojan Hardtop is sure to turn heads in every harbor. With a fully sheltered helm and canvassed aft deck, there's plenty of room f... View Details

    View 40 Photos and Details Contact Seller
    $10,900
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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

    Arriving at Pier 33 soon! 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... View Details

    View 30 Photos and Details Contact Seller
    $34,900
    VIEW DETAILS
  • 1999 Sea Ray 370 Express Cruiser

    1999 Sea Ray 370 Express Cruiser

    $79,900
    Saint Joseph, MI

    Available and on display! The superbly designed 370 Express Cruiser features the full realm of Sea Ray luxuries, plus desirable characteristics unique to the EC series -- expansive... View Details

    View 46 Photos and Details Contact Seller
    $79,900
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  • 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
  • 2017 Scout 225 XSF

    2017 Scout 225 XSF

    $64,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Fishing
    • 22' / 0'
    • 2017 / Used
    • $64,900

    !Currently stored offsite, available soon! Turn heads on the water with this clean 2017 Scout 225 XSF, a premium bay/near-shore center console known for its blend of performance,... View Details

    View 14 Photos and Details Contact Seller
    $64,900
    VIEW DETAILS
  • 2024 Chaparral 267 SSX

    2024 Chaparral 267 SSX

    $140,000
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 26' / 0'
    • 2024 / Used
    • $140,000

    Currently Inside Heated Storage, More Pictures To Come In Spring! The Chaparral 267 SSX is breaking barriers and setting the standard in quality. Equipped with state of the art du... View Details

    View 44 Photos and Details Contact Seller
    $140,000
    VIEW DETAILS
  • 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
    VIEW DETAILS
Showing 757 to 777 of 1,172 boats found.
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