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Boats for sale in Chicago Illinois

There are 1171 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
1,171 boats found within 100 miles out of 14,788 Boats Found
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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
    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
  • 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
    VIEW DETAILS
  • 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
    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
  • 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
  • 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
  • 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
    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
  • 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
  • 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
    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
    VIEW DETAILS
  • 2026 Chaparral 21 SSi

    2026 Chaparral 21 SSi

    $73,189
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 21' / 8'
    • 2026 / New
    • $73,189

    See this New 2026 Chaparral 21 SSi! How much fun can you pack into one summer? Plenty, aboard your new Chaparral. Trailerable to your favorite destinations. Nimble, efficient and p... View Details

    View 36 Photos and Details Contact Seller
    $73,189
    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 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
  • 2019 Formula 350 Crossover Bowrider

    2019 Formula 350 Crossover Bowrider

    $325,000
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 35' / 10'
    • 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
  • 2018 Chaparral Vortex 223 VRX

    2018 Chaparral Vortex 223 VRX

    $47,700
    Saint Joseph, MI
    • Saint Joseph, MI
    • Jet boat
    • 22' / 8'
    • 2018 / Used
    • $47,700

    Chaparral put all the knowledge we've learned about boat building in the last 50 years into the 223 VRX. The end result is a family jet boat that's priced right, built right and ex... View Details

    View 39 Photos and Details Contact Seller
    $47,700
    VIEW DETAILS
  • Price Drop 2007 Cobalt 323

    2007 Cobalt 323

    $89,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Runabout
    • 32' / 10'
    • 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 53 Photos and Details Contact Seller
    $89,900
    VIEW DETAILS
  • 2007 Yamaha SX230

    2007 Yamaha SX230

    $24,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Jet boat
    • 23' / 8'
    • 2007 / Used
    • $24,900

    This sweet Yamaha SX 230 with twin 140 hp jet drives is guaranteed fun for the family! Ski, tube, and cruise in the river or on the Big Lake with your friends and family! This boat... View Details

    View 24 Photos and Details Contact Seller
    $24,900
    VIEW DETAILS
  • 2025 Chaparral 23 SSi

    2025 Chaparral 23 SSi

    $96,864
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 23' / 8'
    • 2025 / New
    • $96,864

    In Stock Now See the Chaparral 23 SSi, our best-selling 23-footer! This 23 SSi is superbly equipped with Mercury 300 HP Bravo 3 MPI power and many Chaparral extras. Trailer include... View Details

    View 38 Photos and Details Contact Seller
    $96,864
    VIEW DETAILS
Showing 526 to 546 of 1,171 boats found.
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