Grady White Boats in Chicago

Browse boats for sale in Chicago, IL, and find your next boat for days on Lake Michigan or along the Chicago River. With a strong local boating culture and easy access to waterfront destinations, Chicago offers options for cruising, fishing, and enjoying time on the water. Explore new and used inventory, including popular choices like powerboats and sailboats. Listings from nearby areas may also appear, giving you more options to compare by price, boat type, and features. View available boats, narrow your search, and contact sellers to take the next step toward getting on the water.