• Boats
  • Sailboat
    Within 100 Miles Of
    Chicago, Illinois

Filter Boats By

Filters

from

Boat Type / Category

Sailboat boats for sale in Chicago Illinois

There are 20 new and used Sailboat boats for sale in Chicago, Illinois. Explore Sailboat brands like Hunter, Beneteau, Marlow Hunter, Dufour, Bayfield, and Oyster on BoatCrazy. View a wide selection of Sailboat boats from $15,000 to $695,000.
  • Back
  • Boats
  • Sailboat
    Within 100 Miles Of
    Chicago, Illinois
20 boats found within 100 miles from Chicago, Illinois
Back
Filter
  • 1975 Fales 32 Navigator

    1975 Fales 32 Navigator

    $33,350
    Chicago, IL
    • Chicago, IL
    • Sailboat
    • 32' / 0'
    • 1975 / Used
    • $33,350

    Stock #471796 Reason for selling is "No longer sailing / using the vessel". This Fales has now been on the market more than a month. Please submit your offer today! NICE LOOKING... View Details

    View 10 Photos and Details Contact Seller
    $33,350
    VIEW DETAILS
  • 1982 Ericson 36 Ron Holland Edition

    1982 Ericson 36 Ron Holland Edition

    $26,500
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Sailboat
    • 36' / 0'
    • 1982 / Used
    • $26,500

    Stock #477838 Reason for selling is "Not using it enough.". This Ericson Yachts has now been on the market more than a month. Please submit your offer today! 1982 Ericson 36 Sai... View Details

    View 10 Photos and Details Contact Seller
    $26,500
    VIEW DETAILS
  • 2007 Hunter 38

    2007 Hunter 38

    $114,900
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 12'
    • 2007 / Used
    • $114,900

    007 Hunter 38 Available for viewing!! Overview If you’ve been waiting for the right cruising sailboat—this is it. This 2007 Hunter 38 delivers the perfect combination of perfor... View Details

    View 30 Photos and Details Contact Seller
    $114,900
    VIEW DETAILS
  • 2026 Dufour 37

    2026 Dufour 37

    $369,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 12'
    • 2026 / New
    • $369,000

    2026 Dufour 37 This 2026 Dufour 37 is a rare opportunity to acquire a turnkey, revenue-producing sailboat with established demand, full utilization, and professional management al... View Details

    View 18 Photos and Details Contact Seller
    $369,000
    VIEW DETAILS
  • 1996 Caliber 1 35 LRC

    1996 Caliber 1 35 LRC

    $85,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 11'
    • 1996 / Used
    • $85,000

    1996 Caliber 35 LRC "Archangel" This is a single owner vessel, purchased new in '96 and used exclusivley for cruising Lake Michigan. The boat has been really well cared for as wa... View Details

    View 30 Photos and Details Contact Seller
    $85,000
    VIEW DETAILS
  • 1989 Hunter 30

    1989 Hunter 30

    $22,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 11'
    • 1989 / Used
    • $22,000

    1989 Hunter 30 "Silent Knight" This is a very nice freshwater boat, very well maintained for an 89'. - Starting aft, this boat offers the swim platform with stainless steel swim... View Details

    View 30 Photos and Details Contact Seller
    $22,000
    VIEW DETAILS
  • 1987 Hunter Legend 37

    1987 Hunter Legend 37

    $35,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 12'
    • 1987 / Used
    • $35,000

    1987 Hunter Legend 37 Large main salon with dinnett to port and settee to starboard, nav station to starboard, full galley with 2 burner stove / oven, double stainless sink and re... View Details

    View 18 Photos and Details Contact Seller
    $35,000
    VIEW DETAILS
  • 1985 C & C Landfall 39

    1985 C & C Landfall 39

    $59,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 12'
    • 1985 / Used
    • $59,000

    C&C Landfall 39 A proven offshore cruising yacht with a balance of performance and comfort, this C&C Landfall 39 is fully equipped and extensively upgraded. Built by C&C Yachts, s... View Details

    View 30 Photos and Details Contact Seller
    $59,000
    VIEW DETAILS
  • 2012 Beneteau Oceanis 45

    2012 Beneteau Oceanis 45

    $283,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 45' / 14'
    • 2012 / Used
    • $283,000

    2012 Beneteau Oceanis 45 US Elegance Pack - Simrad IS20 Graphic Displays (Log, Speed, Depth & Wind System @ Starboard & Port Helm) - Cockpit Shower - Indirect Lighting With LED I... View Details

    View 30 Photos and Details Contact Seller
    $283,000
    VIEW DETAILS
  • 1983 Marlow Hunter 27 Cherubini

    1983 Marlow Hunter 27 Cherubini

    $15,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 0'
    • 1983 / Used
    • $15,000

    This 1983 Hunter 27 (Tall Rig) has been cared for and loved for many years. The boat has been maintained to a very high level, which will leave a lucky new owner with less headache... View Details

    View 30 Photos and Details Contact Seller
    $15,000
    VIEW DETAILS
  • 1982 Campion C320

    1982 Campion C320

    $15,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 10'
    • 1982 / Used
    • $15,000

    11982 Campion C-320 Pilot House "LINDISFARNE" LOA: 32ft Beam: 10ft 1in Bridge Clearance: 52ft Engine: 17hp Volvo Diesel Model: MD7B Radar VHF Radio Hood mainsail - fair c... View Details

    View 30 Photos and Details Contact Seller
    $15,000
    VIEW DETAILS
  • 1994 Pacific Seacraft 34

    1994 Pacific Seacraft 34

    $100,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 10'
    • 1994 / Used
    • $100,000

    1994 Pacific Seacraft 34 "Esmerelda" This William Crealock designed 1994 Pacific Seacraft cutter is ready for your next sailing adventure. The vessel has been stored indoors thro... View Details

    View 30 Photos and Details Contact Seller
    $100,000
    VIEW DETAILS
  • 2019 Beneteau Oceanis 41.1

    2019 Beneteau Oceanis 41.1

    $289,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 40' / 13'
    • 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
  • 2007 Marlow Hunter 25

    2007 Marlow Hunter 25

    $17,900
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 8'
    • 2007 / Used
    • $17,900

    2007 Hunter 25 Year: 2007 Builder: Hunter Marine Model: Hunter 25 Length Overall: 24'6" Hull Material: Fiberglass Engine Type: 2010 Outboard-9.9 Tohatsu Fuel Type: Gas Usag... View Details

    View 30 Photos and Details Contact Seller
    $17,900
    VIEW DETAILS
  • 2000 Hunter 410

    2000 Hunter 410

    $95,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 13'
    • 2000 / Used
    • $95,000

    2000 Hunter 410 - "Cabaret" This Hunter has been maintained quite well over its life, kept on the Great Lake Michigan and moored at the Racine Yacht Club. Take your family sailing... View Details

    View 30 Photos and Details Contact Seller
    $95,000
    VIEW DETAILS
  • 1983 O Day 34

    1983 O Day 34

    $35,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 11'
    • 1983 / Used
    • $35,000

    1983 O'Day 34 "Dawn Treader" The O'Day 34. This boat offers plenty of comfortable room below deck and a spacious cockpit which make this a great weekend cruiser and daysailer! Wi... View Details

    View 30 Photos and Details Contact Seller
    $35,000
    VIEW DETAILS
  • 1987 Oyster 46.5

    1987 Oyster 46.5

    $145,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 14'
    • 1987 / Used
    • $145,000

    1987 Oyster 46.5 "Here Be Dragons" LOA: 46ft 2in BEAM: 14ft DRAFT: 6ft 6in DISPLACEMENT: 32,000 Lbs FUEL: 120 Gal FRESH WATER: 220-250 Gal (With Water Heater!) HOLDING: ~26... View Details

    View 30 Photos and Details Contact Seller
    $145,000
    VIEW DETAILS
  • 1987 Bayfield 32C

    1987 Bayfield 32C

    $28,999
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 10'
    • 1987 / Used
    • $28,999

    1987 Bayfield 32C Designed by Ted Gozzard and hand-crafted in Ontario, Canada, the 32C is one of a select few Bayfield 32s ever built with the extended tall rig. The difference is... View Details

    View 30 Photos and Details Contact Seller
    $28,999
    VIEW DETAILS
  • 2019 Beneteau Oceanis 35.1

    2019 Beneteau Oceanis 35.1

    $159,900
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 12'
    • 2019 / Used
    • $159,900

    2019 Beneteau Oceanis 35.1 | Freshwater | Turnkey If you’ve been searching for a late-model cruising sailboat in the 35–36 ft range, you already know how competitive this segment... View Details

    View 24 Photos and Details Contact Seller
    $159,900
    VIEW DETAILS
  • 2024 Dufour D470

    2024 Dufour D470

    $695,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 0' / 15'
    • 2024 / New
    • $695,000

    2024 Dufour 470 | 3 Cabin Owner Version | Loaded | Available Now – No Wait If you’ve been researching new cruising sailboats in the 45–50 ft range, you already know: The biggest... View Details

    View 8 Photos and Details Contact Seller
    $695,000
    VIEW DETAILS
Showing 1 to 20 of 20 boats found.

Sailboat Boats on Boatcrazy

As the name suggests, sailboats rely partly or entirely on the power of the wind for propulsion and use large cloth or synthetic sails for this purpose.

We have many kinds of Sailboats for Sale and as they differ by use, size and strength – it’s important to consider carefully which type of sailboat is best for your intended use.

Sailboat Boats manufacturers on Boatcrazy

When looking to buy a quality Sailboat consider these top Sailboat Manufacturers

Hallberg-Rassy, Dufour, Beneteau, Brewer, Bluewater, Irwin, Herve, Endeavour, Corsair, Sabre, Hardin, Gulfstar, Willard.

Sailboat Boats For Sale by State

Sailboat Boats Frequently Asked Questions

How much does an average Sailboat cost?

Cruising sailboat prices vary. The average cost of new cruising sailboats is about $250K; however they range from around 100k all the way up to 500k. For used models you should expect an expense between 10k-100k.

To date, the average price for sailboat insurance has been around $250 to $1500 per year. This varies based on what type of policy and how much coverage you need - but it's usually cheaper than power boat insurance!

Obviously, the best time to buy a Sailboat is when the time is right for your budget! But there is never a bad time, as long as you are ready to handle the responsibility of owning such a boat, and on Boatcrazy, we have plenty to choose from! Each season also has its advantages and disadvantages, so understanding what each season presents can be of great help in finding a better deal.

Cruising Sailboats are the ultimate way to explore long distances, but for a Sailboat to travel a long journey, the boat needs to be livable, should have the right amenities and plenty of storage space, and should be able to travel at a decent speed. Moreover, it should be strong and durable.

Sailing through the Indian Ocean has come to be a challenging task owing to its characteristic of being one of the most deadly ocean waters in the world for Sailboats.

Centerboards are an essential part of any boat, but they're especially important on smaller vessels that don't have the weight or power to self-propel. Centerboard equipped boats range in length from 12 - 25 feet and work as both stability and steering systems.