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Boats for sale in Chicago Illinois

There are 1161 new and used boats for sale in Chicago, Illinois. Browse Fishing, Cruiser, Center Console, Pontoon, Runabout, and Ski & Wake from brands like Scout, Sea Ray, Yamaha, Harris, Barletta, and Bayliner 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
1,161 boats found within 100 miles out of 13,655 Boats Found
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  • 2026 Harris Grand Mariner 270

    2026 Harris Grand Mariner 270

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • Pontoon
    • 29'
    • 2026 / New
    • Call for price

    Introducing the 2026 Harris Grand Mariner 270. Innovative, powerful, and sleek. Show your friends the true meaning of "luxury" aboard the gorgeously styled Grand Mariner. Spectacul... View Details

    View 30 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Harris Sunliner 250 Sport

    2026 Harris Sunliner 250 Sport

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • Pontoon
    • 26'
    • 2026 / New
    • Call for price

    Introducing the 2026 Harris Sunliner 250 Sport, crafted for adventure. With flexible seating arrangements and easy style, Sunliner is the pontoon built to fit your family. Make a s... View Details

    View 20 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Harris Sunliner 230 Sport

    2026 Harris Sunliner 230 Sport

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • Pontoon
    • 23'
    • 2026 / New
    • Call for price

    Introducing the 2026 Harris Sunliner 230 Sport, crafted for adventure. With flexible seating arrangements and easy style, Sunliner is the pontoon built to fit your family. Make a s... View Details

    View 30 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Harris Grand Mariner 230

    2026 Harris Grand Mariner 230

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • Pontoon
    • 28'
    • 2026 / New
    • Call for price

    Innovative, powerful, and sleek-the 2026 Harris Grand Mariner 230. Show your friends the true meaning of "luxury" aboard the gorgeously styled Grand Mariner. Spectacular power and... View Details

    View 30 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Harris Grand Mariner 250

    2026 Harris Grand Mariner 250

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • Pontoon
    • 28'
    • 2026 / New
    • Call for price

    Innovative, powerful, and sleek-the 2026 Harris Grand Mariner 250. Show your friends the true meaning of "luxury" aboard the gorgeously styled Grand Mariner. Spectacular power and... View Details

    View 30 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • Price Drop 2025 Sea Ray SDX 270

    2025 Sea Ray SDX 270

    $182,584
    Pewaukee, WI
    • Pewaukee, WI
    • Runabout
    • 27'
    • 2025 / New
    • $182,584

    Contact us to find out ALL available savings! Act fast on this limited-time offer! The SDX 270 delivers on maximum capability to make a full day on the water easy to enjoy. With pl... View Details

    View 14 Photos and Details Contact Seller
    $182,584
    VIEW DETAILS
Showing 1156 to 1,161 of 1,161 boats found.
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