Yachts for Sale in Chicago

New & Used Yachts for Sale in Chicago

Browse new and used yachts for sale in Chicago from verified dealers and brokers on Lake Michigan. YachtWay carries motor yachts, sailing yachts, express cruisers, pontoons, and sportfishing vessels listed across Chicago's seven lakefront harbors — Burnham Harbor, DuSable Harbor, Monroe Harbor, Belmont Harbor, Diversey Harbor, Montrose Harbor, and the newly opened Navy Pier Marina, Chicago's only all-transient marina. Chicago sits on the southwestern shore of Lake Michigan: the largest freshwater lake entirely within the United States — with a boating season running April through October and direct access to the full length of the lake and beyond through the Great Loop. Every listing includes manufacturer-verified specifications, high-quality media, and integrated financing tools.

Popular Brands in Chicago on YachtWay

Sea Ray Boats for Sale · Boston Whaler for Sale · Regal Boats for Sale · Tiara Yachts for Sale · Cruisers Yachts for Sale · Beneteau Yachts for Sale · Formula Boats for Sale · Nautique Boats for Sale

Browse More Midwest and US Listings

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Finance your purchase with EasyFund: get pre-qualified without affecting your credit score. For marine insurance, visit MasterCover. For guidance on the buying process, visit the YachtWay Knowledge Center.