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Boats for sale in Chicago Illinois

There are 721 new and used boats for sale in Chicago, Illinois. Browse Pontoon, Cruiser, Runabout, Fishing, Center Console, and Ski & Wake from brands like Sea Ray, Scout, Bayliner, Harris, Yamaha, and Mastercraft on BoatCrazy. View a wide selection of boats from $100 to $2,499,495.
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  • Boats
  • Within 100 Miles Of
    Chicago, Illinois
721 boats found within 100 miles from Chicago, Illinois
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  • 2026 Viaggio LAGO V 22U TRITOON

    2026 Viaggio LAGO V 22U TRITOON

    $49,995
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22'
    • 2026 / New
    • $49,995

    New 2026 Viaggio Lago V22U TRITOON with BF 150 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. Upgrades include: Honda Pre-rig Cable Steering w/ Tilt Steering... View Details

    View 17 Photos and Details Contact Seller
    $49,995
    VIEW DETAILS
  • 2026 Viaggio LAGO Z 22U TRITOON

    2026 Viaggio LAGO Z 22U TRITOON

    $68,749
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22'
    • 2026 / New
    • $68,749

    New 2026 Viaggio Lago Z22U Pontoon with BF 200 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. Upgrades include: Tube Protectant Pontoon Side Keel (Port & Starb... View Details

    View 14 Photos and Details Contact Seller
    $68,749
    VIEW DETAILS
  • 2026 Viaggio LAGO X 22Q TRITOON

    2026 Viaggio LAGO X 22Q TRITOON

    $51,939
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22'
    • 2026 / New
    • $51,939

    New 2026 Viaggio Lago X22Q TRITOON with BF 140 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. ** Boat Show Savings + Honda Buyers Choice Sales Event Upgrades inc... View Details

    View 33 Photos and Details Contact Seller
    $51,939
    VIEW DETAILS
  • Price Drop 1988 Four Winns 200 HORIZON

    1988 Four Winns 200 HORIZON

    $500
    La Porte, IN
    • La Porte, IN
    • Cruiser
    • 20'
    • 1988 / Used
    • $500

    1988 Four Winns 200 Horizon – DIY Project Opportunity with titles! A classic bowrider with restoration potential, this 1988 Four Winns 200 Horizon is ideal for hands-on boaters lo... View Details

    View 10 Photos and Details Contact Seller
    $500
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  • Price Drop 1994 Rinker 190 CAPTIVA (175 HP MCM)

    1994 Rinker 190 CAPTIVA (175 HP MCM)

    $900
    La Porte, IN
    • La Porte, IN
    • Cruiser
    • 19'
    • 1994 / Used
    • $900

    ️ 1994 Rinker 190 Captiva – Affordable Bowrider Opportunity Turn heads on the water with this classic 19-foot Rinker Captiva—an ideal platform for restoration or repower. With its... View Details

    View 12 Photos and Details Contact Seller
    $900
    VIEW DETAILS
  • 2026 Viaggio LAGO V 20S TRITOON

    2026 Viaggio LAGO V 20S TRITOON

    $51,052
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 20'
    • 2026 / New
    • $51,052

    New 2026 Viaggio Lago V20S TRITOON with BF 140 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. Upgrades Include: Tube Protectant Pontoon Side Keel (Port & Starboar... View Details

    View 15 Photos and Details Contact Seller
    $51,052
    VIEW DETAILS
  • 2026 Viaggio LAGO V 22S TRITOON

    2026 Viaggio LAGO V 22S TRITOON

    $54,573
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 20'
    • 2026 / New
    • $54,573

    The 2026 Viaggio Lago V22S Tritoon blends modern styling, upgraded comfort, and proven Viaggio performance—now available at Fay’s Marina in La Porte, Indiana 46350. Powered by the... View Details

    View 13 Photos and Details Contact Seller
    $54,573
    VIEW DETAILS
  • 2007 Bayliner 195BR

    2007 Bayliner 195BR

    $9,500
    La Porte, IN
    • La Porte, IN
    • Bowrider
    • 0'
    • 2007 / Used
    • $9,500

    2007 Bayliner 195 Bowrider – Clean, Versatile, and Ready for the Water This 2007 Bayliner 195 BR is a solid, family-friendly bowrider with the power and layout to handle everythin... View Details

    View 18 Photos and Details Contact Seller
    $9,500
    VIEW DETAILS
  • 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

    View 5 Photos and Details Contact Seller
    $2,500
    VIEW DETAILS
  • Price Drop 2014 Chaparral 287 SSX

    2014 Chaparral 287 SSX

    $69,600
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 28'
    • 2014 / Used
    • $69,600

    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
    $69,600
    VIEW DETAILS
  • 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
  • 2007 Sweetwater SW 1986 RE-3 Gate

    2007 Sweetwater SW 1986 RE-3 Gate

    $10,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Pontoon
    • 19'
    • 2007 / Used
    • $10,900

    Trailer Included! See this 2007 Sweetwater SW 1986 RE-3 Gate, an affordable pontoon boat that combines comfort and functionality. With an overall length of approximately 19.17 fee... View Details

    View 25 Photos and Details Contact Seller
    $10,900
    VIEW DETAILS
  • Price Drop 1996 Monterey 276

    1996 Monterey 276

    $20,000
    Saint Joseph, MI

    Stock #494642 This Monterey has been on the market for more than 30 days (Jun 16th). If you are thinking of making an offer, submit it today and let's make a deal! Updated seats... View Details

    View 10 Photos and Details Contact Seller
    $20,000
    VIEW DETAILS
  • Price Drop 1999 Sea Ray 290 Sundancer

    1999 Sea Ray 290 Sundancer

    $35,900
    Saint Joseph, MI

    This 1999 Sea Ray 290 Sundancer is the perfect blend of weekend cruiser, sunset chaser, and floating cottage. Powered by twin mercury engines, this popular express cruiser offers t... View Details

    View 51 Photos and Details Contact Seller
    $35,900
    VIEW DETAILS
  • 2000 Pursuit 3400 Express

    2000 Pursuit 3400 Express

    $137,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 33'
    • 2000 / Used
    • $137,900

    Currently in water offsite, By Appointment Only Please! This Freshwater Pursuit 3400 Express has long been respected for its exceptional ride, quality construction, and versatile... View Details

    View 84 Photos and Details Contact Seller
    $137,900
    VIEW DETAILS
  • 2016 Chaparral 257 SSX

    2016 Chaparral 257 SSX

    $72,500
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 25'
    • 2016 / Used
    • $72,500

    Boating's best 25-footer! Step onboard the sensational 257 SSX and experience the perfect mix of classic elegance and high tech innovation. Bow to stern, the eye appeal is simply s... View Details

    View 31 Photos and Details Contact Seller
    $72,500
    VIEW DETAILS
  • 2025 Robalo R160 Center Console

    2025 Robalo R160 Center Console

    $41,430
    Saint Joseph, MI

    The R160 makes every on-water adventure more fun in a size that's easy to trailer and store. But don't think that it isn't designed with performance in-mind. Featuring the same on-... View Details

    View 26 Photos and Details Contact Seller
    $41,430
    VIEW DETAILS
  • 2026 Chaparral SSX 6

    2026 Chaparral SSX 6

    Call for price
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 26'
    • 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
  • Price Drop 2002 Regal 3860

    2002 Regal 3860

    $94,999
    Saint Joseph, MI

    Stock #467673 Reason for selling is "New Adventure!". This Regal has now been on the market a couple months. Looking for any offers! Incredible luxury, performance, and a sound... View Details

    View 10 Photos and Details Contact Seller
    $94,999
    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 2002 Maxum 2700 SCR

    2002 Maxum 2700 SCR

    $29,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 28'
    • 2002 / Used
    • $29,900

    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
    $29,900
    VIEW DETAILS
Showing 295 to 315 of 721 boats found.
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