This route enabled shippers to avoid the crowded railroad yards and sidings of Chicago.

Around 2:00 pm on October 22, 1929, the Milwaukee sailed off on Lake Michigan into a storm bound for Grand Haven, and was lost.

The Milwaukee had been loaded earlier that day with 27 railcars, with freight including lumber, perishable foods, bathtubs and Nash automobiles.

[4][5] The Milwaukee was last seen passing by U.S. Lightship 95 (LV-95/WAL-519), a ship anchored three miles offshore, serving as a lighthouse.

Some of the lifeboats were launched by the crew, and the bodies of two crew members wearing SS Milwaukee lifejackets were picked up two days later by the steamer, SS Steel Chemist, off Kenosha, Wisconsin, and two more, including the body of Captain McKay, were found by the coast guard at Kenosha later that day.

[6] A lifeboat containing four dead crew members was found on 26 October floating near Holland, Michigan, on the other side of the lake.

For example, the story was retold by marine historian Dwight Boyer in his Ghost Ships of the Great Lakes in 1968.

[9] As a result of the loss of SS Milwaukee, the Grand Trunk needed a new train ferry.

[12] In March 2006, the History Channel television program Deep Sea Detectives premiered an episode entitled "Train Wreck in Lake Michigan", which profiled the loss of the Milwaukee through historical documents, interviews with historians and dives to the wreck itself.

The show highlighted the fact that there were missing hatch covers between the track deck and compartments below, including the engine room and the crew quarters (Flicker), that probably allowed those areas to become flooded and thus contributed to the sinking of the ship.