44 boats and yachts for sale in Chicago, Illinois, priced $5,900 to $1,246,299, including powerboats, cruisers & motor yachts, sailboats. 40 of the 44 are listed by their owners; the rest are dealer or broker listings, each badged so you know who you are dealing with. Every listing badged FSBO, Broker or Dealer — contact each seller directly. Newest added 2026-11-08.
44 boats are listed for sale in Chicago, Illinois — 9 added in the last 30 days — at a median asking price of $35,995, and 91% are offered directly by their owners.
Sea Ray8Sunseeker3Boston Whaler2Catalina2Chris Craft2Beneteau1
Figures come from the listings on this page today. A length band appears only when at least 5 listings state a length and a price.