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craigslist

For Sale "sailboat" in Chicago

  1. see also
  2. 2005 HUNTER 33 SAILBOAT LOADED RACINE WI MARINA
    $79,000
    LAKE IN THE HILLS
  3. ARTWORK LARGE SAILBOAT
    $30
    SOUTH BARRINGTON
  4. Mid-century brass torch cut MCM ship sailboat
    $25
    Crestwood
  5. Laser cut plywood Sailboat building kit
    $60
    northwest suburbs
  6. Sailing Partners + Lessons (no experience required) 2025
    $3,500
    Chicago
  7. Hunter 34' Boat
    $14,990
    Waukegan
  8. Alcort Sailfish mahogany sailboat
    $800
    Wheaton
  9. '22 XCat Sail with Extras
    $8,000
    Manchester
  10. Framed Wall Art - Dale Cooper Golf watercolor -OR- Sailboat *$10 Each
    $10
    Lemont
  11. Thistle Sailboat 17 foot
    $3,500
    waterford
  12. Sunfish Sailboat Centerboard and Mast
    $90
    chicago
  13. 470 sailboat
    $2,500
    Knox
  14. Sailboat Yacht Sterling Silver Wall Art
    $165
    n/chicago il
  15. 14' O'Day Javelin
    $1,000
    Wauconda
  16. Nautical Pyrography Leather Sailboat Original Sailing Art
    $25
    downtown Naperville
  17. 1981 Cal 25 MK-II Sailboat
    $5,000
    Chicago
  18. Sailboat at Sunset Canvas Print
    $25
    Elgin
  19. Pearson 323 Sailboat -
    $21,000
    Nautical Donations/Crowleys Yacht Yard
  20. Pearson 323 Sailboat
    $21,000
    Nautical Donations/Crowleys Yacht Yard
  21. Sailboat and Birds Wall Art
    $85
    n/chicago il
  22. Hobie Cat 16 in Wilmette
    $500
    Wilmette
  23. 30ft Sailboat 2026 Fractional Lease (1 spot left)
    $1,000
    Montrose harbor
  24. Want to sail, learn to sail, or be a part boat owner?
    $1,000
    Monroe Harbor
  25. S-2 9.2 ( 30 ft ) sailboat
    $14,500
    Nautical Donations/Crowleys Yacht Yard
  26. SUNFISH SAILBOAT PARTS
    $10
    WILMETTE, ILLINOIS
  27. SUNFISH SAILBOAT PARTS, BOW HANDLE
    $20
    WILMETTE, ILLINOIS
  28. SUNFISH SAILBOAT SWIVELING JAM CLEAT
    $40
    WILMETTE, ILLINOIS
  29. MAIN SAIL FOR O'DAY 28' SAILBOAT
    $300
    WILMETTE, ILLINOIS
  30. Sailing Partners + Lessons (no experience required) 2026
    $4,000
    Chicago
  31. vintage,aluminum,grumman sailboats ,sail boat,sailing dinghy 9 foot
    $2,500
    25 miles south of chicago
  32. Sailboat model
    $10
    Downers Grove
  33. 1984 S2 9.2C sailboat
    $0
    northwest suburbs
  34. 1984 S2 9.2C Center Cockpit Sailboat
    $22,500
    city of chicago
  35. Hunter 44 Deck Salon
    $125,000
    Chicago
  36. Sailboat with Motor Sails Stand up Paddle Boards Montrose Harbor
    $850
    Chicago
  37. 4 Waechtersbach Cobalt Blue Sailboat Coffee Mugs Vintage Cups Germany
    $125
    West Loop Gate
  38. Dead & Busted Sailboat Blocks - Harken 3" HexaRatchet - Schaefer 2.5"
    $20
    West Loop Gate
  39. Nautos Line 39mm Sailboat Block Single Fixed Head+Becket+S-Hook #92315
    $30
    West Loop Gate
  40. Sails for Sirius 28 sailboat
    $111
    Schiller Park
  41. Sailboat Brass sculpture
    $250
    So.West Naperville
  42. Tripp 47
    $40,000
    city of chicago
  43. C&C 34 Sailboat - Upgraded
    $20,000
    Nautical Donations/Crowleys Yacht Yard
  44. 1979 Ericson E27
    $1,000
    Chicago
  45. REDUCED PRICE! Great Old Boat For Sale
    $4,000
    Escanaba
  46. Hobie Cat Getaway, Includes Trailer and Wings - Excellent Condition
    $6,900
    northwest suburbs
  47. 2005 Hunter 44 DS Sailboat (SV Healer)
    $39,500
    city of chicago
  48. Catalina 30TR
    $27,500
    Mokena
  49. Hunter Legend 37.5 sailboat fractional lease - 2026 season
    $5,450
    31st Street Harbor
  50. ⛵AMF Sunfish Sailboat
    $450
    north chicagoland
  51. Laser sailboat from 96 Olympics
    $2,500
    Wheaton
  52. Melges 14 for sale
    $7,700
    Glenview
  53. Sailboat S2 27'
    $11,500
    Springfield, Missouri
  54. 1975 Bristol 40 Sailboat
    $20,000
    Chicago
  55. Sailboat rental
    $150
    Chicago
  56. 1984 Bayfield 40
    $30,000
    Chicago
  57. Steel Stands, FREE Shipping
    $30
    city of chicago
  58. Used Steel Cable, 1/2in - 1in (DIA) x 75ft - 1,050ft
    $85
    city of chicago
  59. Indoor RV Storage - 12X40 Palatine - Trade for Hangar Space
    $325
    Palatine
  60. Indoor Boat and RV Storage - Seasonal and Self - Reserve NOW!
    $123
    Palatine
  61. BRIERE Folk Art Pull Toy Collection EXCELLENT
    $0
    Naperville
  62. 9.8 Electric Start Long shaft
    $400
    northwest suburbs
  63. Items with Sail Boats
    $0
    Deerfield
  64. MC NAUTICAL WOODEN SHIP / BOAT WHEEL vintage
    $58
    Evanston
  65. Indoor RV Storage - Self In & Out - Big 12 Wide 14 Tall Roll Up Doors
    $123
    Palatine
  66. Outboards motors for sale
    $450
    Shorewood
  67. Garage Sale many items, take a look
    $0
    Shorewood
  68. Murphy Nye Sail
    $500
    Wheaton
  69. Anchor – Chain and Rode
    $75
    Chicago
  70. FURLING GENOA JIB FOR CATALINA 27
    $200
    WILMETTE, ILLINOIS
  71. Guywire & Steel Cable – Multiple Sizes & Lengths, Heavy Duty
    $60
    city of chicago
  72. Boat Anchor Mantus 35lb.
    $375
    Schiller Park
  73. Fantasy Family Dream Home Set
    $50
    Montgomery IL
  74. Three Wooden Sailboats Gallery Framed Artwork
    $35
    Harvard
  75. Huge Vintage Framed Signed Oil Painting of Sailboats & Mountains
    $390
    Palatine
  76. Used Steel Cable, 1/2in - 1in (DIA) x 75ft - 1,050ft
    $85
    city of chicago
  77. Vintage Framed Signed Certified Oil Painting of Sailboats
    $250
    Inverness
  78. Steel Stands, FREE Shipping
    $30
    city of chicago
  79. Bayliner boat
    $10,500
    Lincolnwood