• Boats
  • Used Only
    2000' 2025'
    Within 100 Miles Of
    Chicago, Illinois

Filter Boats By

Filters

from

Boat Type / Category

Boats for sale in Chicago Illinois

There are 153 used boats for sale in Chicago, Illinois. Browse Bowrider, Pontoon, Cruiser, Ski & Wake, Sailboat, and Express Cruiser from brands like Chaparral, Sea Ray, Cobalt, Crownline, Malibu, and Bayliner on BoatCrazy. View a wide selection of boats from $300 to $849,900.
  • Back
  • Boats
  • Used Only
    2000' 2025'
    Within 100 Miles Of
    Chicago, Illinois
153 boats found within 100 miles from Chicago, Illinois
Back
Filter
  • 2019 Beneteau Oceanis 41.1

    2019 Beneteau Oceanis 41.1

    $289,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 40'
    • 2019 / Used
    • $289,000

    2019 Beneteau Oceanis 41.1 This 2019 Beneteau Oceanis 41.1 is a rare opportunity to acquire a turnkey, revenue-producing sailboat with established demand, full utilization, and pr... View Details

    View 10 Photos and Details Contact Seller
    $289,000
    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
  • 2005 Sea Ray 500 Sundancer

    2005 Sea Ray 500 Sundancer

    $340,000
    Holland, MI
    • Holland, MI
    • Yacht
    • 50'
    • 2005 / Used
    • $340,000

    02/22/2026 PRICE REDUCED TO $340,000| Motivated Seller Presenting this 2005 Sea Ray 500 Sundancer, a well-maintained freshwater express cruiser located on the Great Lakes and curr... View Details

    View 42 Photos and Details Contact Seller
    $340,000
    VIEW DETAILS
  • 2022 Cruisers 38 GLS

    2022 Cruisers 38 GLS

    $604,900
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 37'
    • 2022 / Used
    • $604,900

    The ultimate family or entertainer's day boat! This stunning 2022 Cruisers Yachts 38 GLS is perfect for those who love to spend time on the water, offering luxurious amenities and... View Details

    View 14 Photos and Details Contact Seller
    $604,900
    VIEW DETAILS
  • 2021 Boston Whaler 420 OUTRAGE

    2021 Boston Whaler 420 OUTRAGE

    $849,000
    Antioch, IL
    • Antioch, IL
    • Yacht
    • 42'
    • 2021 / Used
    • $849,000

    This one owner 2021 Boston Whaler 420 Outrage is fully equipped, SeaKeeper stabilized and powered by quad Mercury 450R's with only 252 fresh water hours. She has been Captain maint... View Details

    View 30 Photos and Details Contact Seller
    $849,000
    VIEW DETAILS
  • 2010 Sea Ray 610 SUNDANCER

    2010 Sea Ray 610 SUNDANCER

    $849,900
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 61'
    • 2010 / Used
    • $849,900

    Fresh water, 2 owner, Lake Michigan boat! Less than 700 pampered hours on 1100 MAN engines. Seller equipped this beauty with a Yacht Controller for fearless docking. 3 staterooms c... View Details

    View 30 Photos and Details Contact Seller
    $849,900
    VIEW DETAILS
Showing 148 to 153 of 153 boats found.
Prev Next