Boats
Search

Sailboats for Sale in Chicago

(1 - 15 of 123)
  1. CLASSIC GEM, 28.5 feet. Charter member in Sailboat Hall of Fame. Universal Atomic four engine (gas), 30 horsepower, excellently maintaine...
    5 hours ago on SpreadMyAd
  2. Comfortable - Single Hander Day Sailing or Cruising the lakes - Set up for single handing, Cruiser sailboat sleeps 5/6, "Stack Pack" Main...
    1 day ago on SpreadMyAd
  3. 2 days ago on CL
  4. … Fast, sleek, yet so functional- this sweetly-sized Oceanis 37 answers the demands and challenges of all kinds ...
  5. 4 days ago on CL
  6. 4 days ago on CL
  7. 12 hours ago on CL
  8. PRICE REDUCED!! MOTIVATED SELLER! WANT TO SELL BEFORE OCTOBER. 31. MAKE AN OFFER!! Up for sale is Tranquility, a 1973 Catalina 27. She is...
    6 days ago on SpreadMyAd
  9. 12 hours ago on CL
  10. 16' US1 sailboat. Ready to sail. Does not include trailer, but I have 1 that I would sell if you need one
    6 days ago on SpreadMyAd
  11. 1961 Seafarer, Polaris. Beautiful. Made in Holland. Good condition. Wooden mast and boom, refinished and in attractive condition. Imron p...
    1 week ago on SpreadMyAd
  12. Newly refurbished 22 feet 1966 Pearson Electra Model 258 Sailboat, comes with 30 ft iron trailer. Includes Jib, Genoa & amp; Main Sails. ...
    1 week ago on SpreadMyAd
  13. 2 days ago on CL
  14. 1 week ago on CL
  15. 1 week ago on CL

SET LOCATION

Important Safety Tips
  • Meet the seller and test drive before you buy.
  • Be cautious of underpriced items.
  • Don’t wire money or take advance payments.
  • Only pay for shipping if you know the seller.

To learn more, visit the Safety Center. Report suspicious listings by clicking on .