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Boats for sale in Chicago Illinois

There are 1635 new and used boats for sale in Chicago, Illinois. Browse Outboard Motors, Fishing, Center Console, Cruiser, Pontoon, and Runabout from brands like Mercury, Scout, Honda, Sea Ray, Yamaha, and Barletta on BoatCrazy. View a wide selection of boats from $300 to $2,549,000.
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  • Boats
  • Within 100 Miles Of
    Chicago, Illinois
1,635 boats found within 100 miles from Chicago, Illinois
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  • 2004 Bayliner 245

    2004 Bayliner 245

    $23,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 24'
    • 2004 / Used
    • $23,900

    Bayliner's 245 Cruiser sports a comfortable cockpit and convenient cabin arrangement. The cockpit area includes a reversible portside companion seat -- converting from a forward fa... View Details

    View 25 Photos and Details Contact Seller
    $23,900
    VIEW DETAILS
  • 2017 Regal 2500 Bowrider

    2017 Regal 2500 Bowrider

    $69,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 26'
    • 2017 / Used
    • $69,900

    This 2017 Regal 2500 Bowrider is the kind of boat that makes people suddenly volunteer to bring the snacks. Sleek, sporty, and loaded with Regal style and ready for her next captai... View Details

    View 48 Photos and Details Contact Seller
    $69,900
    VIEW DETAILS
  • 2003 Chaparral 260 SSi

    2003 Chaparral 260 SSi

    $34,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 27'
    • 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
  • 1995 Gibson 44 Classic

    1995 Gibson 44 Classic

    $79,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Houseboat
    • 44'
    • 1995 / Used
    • $79,900

    See this well-loved and well-cared-for Gibson 44. "Lou's Yourself" has always been boated in fresh water, is beautifully decored and loaded with accessories. Twin Crusader 454's, W... View Details

    View 74 Photos and Details Contact Seller
    $79,900
    VIEW DETAILS
  • 2022 Other 22QL

    2022 Other 22QL

    $29,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Pontoon
    • 22'
    • 2022 / Used
    • $29,900

    Hit the water now with this 2022 Nepallo 22QL tritoon, the perfect blend of performance, comfort, and style. Powered with a 115HP Suzuki for smooth cruising and equipped with a tri... View Details

    View 23 Photos and Details Contact Seller
    $29,900
    VIEW DETAILS
  • 2002 Regal 3860

    2002 Regal 3860

    $109,000
    Saint Joseph, MI

    Stock #467673 Reason for selling is "New Adventure!". This Regal has recently been added to market (May 1st). Submit your offer today! Incredible luxury, performance, and a soun... View Details

    View 10 Photos and Details Contact Seller
    $109,000
    VIEW DETAILS
  • 1999 Trojan 360 Express

    1999 Trojan 360 Express

    $68,900
    Saint Joseph, MI

    Spacious and Sporty, this Trojan (by Carver) 360 Express is the perfect family boat for cruising and enjoying the water! It is equipped with a Kohler generator for those hot summer... View Details

    View 32 Photos and Details Contact Seller
    $68,900
    VIEW DETAILS
  • Price Drop 2024 Cobalt R8 Outboard

    2024 Cobalt R8 Outboard

    $199,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 27'
    • 2024 / Used
    • $199,900

    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
    $199,900
    VIEW DETAILS
  • 2007 Chaparral 350 Signature

    2007 Chaparral 350 Signature

    $129,500
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 37'
    • 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'
    • 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
  • Price Drop 2018 Chaparral Vortex 203 VRX

    2018 Chaparral Vortex 203 VRX

    $32,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Jet boat
    • 20'
    • 2018 / Used
    • $32,900

    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
    $32,900
    VIEW DETAILS
  • 2000 Crownline 290 CR

    2000 Crownline 290 CR

    $34,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 31'
    • 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
  • 2017 Chaparral 330 Signature

    2017 Chaparral 330 Signature

    $194,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 33'
    • 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'
    • 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'
    • 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
  • 2019 Formula 350 Crossover Bowrider

    2019 Formula 350 Crossover Bowrider

    $325,000
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 35'
    • 2019 / Used
    • $325,000

    See this Gorgeous fresh-water Formula 350 CBR with just 140 engine hours! Recent price reduction. Ready to go boating now. The 350 CBR offers an ideal combination of luxurious cock... View Details

    View 53 Photos and Details Contact Seller
    $325,000
    VIEW DETAILS
  • 2007 Cobalt 323

    2007 Cobalt 323

    $89,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Runabout
    • 32'
    • 2007 / Used
    • $89,900

    If you're in search of the perfect combination of luxury, performance, and offshore capabilities, look no further than this 2007 Cobalt 323. Cobalt is known for its sleek design an... View Details

    View 52 Photos and Details Contact Seller
    $89,900
    VIEW DETAILS
  • 2002 Maxum 2700 SCR

    2002 Maxum 2700 SCR

    $32,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 28'
    • 2002 / Used
    • $32,900

    This one-owner 2002 Maxum 2700 SCR has spent its life on the fresh waters of Southwest Michigan and shows the care you hope to find in a well-kept family cruiser. With sleek stylin... View Details

    View 49 Photos and Details Contact Seller
    $32,900
    VIEW DETAILS
  • 2006 Chaparral 310 Signature

    2006 Chaparral 310 Signature

    $64,900
    Saint Joseph, MI

    This 2006 Chaparral 310 Signature is a sleek and luxurious cruiser designed for thosewho appreciate both performance and comfort on the water. With a length overall of 33 feet and... View Details

    View 35 Photos and Details Contact Seller
    $64,900
    VIEW DETAILS
  • 2022 Robalo R242 Explorer

    2022 Robalo R242 Explorer

    $119,900
    Saint Joseph, MI

    This Freshwater only Robalo 242 Explorer is at the top of it's class and for good reason. This 24 foot platform is the pinnacle of what the Explorer series is all about. Providing... View Details

    View 50 Photos and Details Contact Seller
    $119,900
    VIEW DETAILS
  • Price Drop 1997 Bayliner 2655 Ciera

    1997 Bayliner 2655 Ciera

    $18,800
    Harvard, IL

    Stock #365912 Video of this vessel available at www [dot] popsells [dot] com/view/365912 ANY and ALL offers will be put in front of our seller! Submit your offer today! FRESH WA... View Details

    View 10 Photos and Details Contact Seller
    $18,800
    VIEW DETAILS
Showing 589 to 609 of 1,635 boats found.
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