In 1880, the Fleetwing began running lumber for Chicago's largest lumber yard, the John Spry Lumber Company, ending her glory days racing other grain clippers for the Straits of Mackinaw. Facing increasing competition from steam-powered vessels and railroads, she now hauled lumber to Chicago from Michigan's Lower Peninsula mills on Lake Huron, often carrying no return cargo, probably due to the time required or the difficulty of locating one.

While business appeared to be brisk, profits were not forthcoming. In January, 1884, Captain Andrew McGraw mortgaged the entire vessel, including her rig, anchors, boats, etc., to James McGraw (probably a relative) for $4,000 at 7 percent interest for one year.

She was rebuilt in 1885 (to what degree is unknown) and was recaulked both in 1886 and in 1887. The vessel was released from the mortgage in March, 1888. The terms of the mortgage required that the vessel be insured, and, if it were willfully or negligently damaged or destroyed, the mortgager was given the right to take possession of the vessel and collect his unpaid principal from the sale of the ship. The last clause may have had some bearing on the manner in which the schooner was eventually lost.

In her final years of service, the Fleetwing also made runs to Menominee, located in Michigan's Upper Peninsula. These trips averaged a little over seven days.

Read the tale of the Fleetwing's final voyage.