On 27 July of her 1903 inaugural season, the ship struck the laid-up tugboat George W. Gardner, which sank at its dock at the Lake Street Bridge in Chicago.

On 5 August 1906, another listing incident occurred, which resulted in complaints filed against the Chicago-South Haven Line that had purchased the ship earlier that year.

[4] On 24 July 1915, Eastland and four other Great Lakes passenger steamers—Theodore Roosevelt, Petoskey, Racine, and Rochester—were chartered to take employees from Western Electric Company's Hawthorne Works in Cicero, Illinois to a picnic in Michigan City, Indiana.

In June 1914, Eastland had again changed ownership, this time bought by the St. Joseph and Chicago Steamship Company, with captain Harry Pederson appointed the ship's master.

In 1914, the company removed the old hardwood flooring of the forward dining room on the cabin level and replaced it with 2 inches (51 mm) of concrete.

Consequently, hundreds were trapped inside by the water and the sudden rollover, and some were crushed by heavy furniture, including pianos, bookcases, and tables.

Captain John O'Meara and the crew of the nearby vessel Kenosha responded quickly by pulling alongside the hull to allow stranded passengers to leap to safety.

Other notable heroes of the day included Peter Boyle, a deckhand from the SS Petoskey who drowned saving passengers, and Helen Repa, a Western Electric nurse who commanded much of the rescue operation.

Many of the passengers on Eastland were immigrants, with large numbers from present-day Czech Republic, Poland, Norway, Germany, Ireland, Sweden, Denmark, Italy, Hungary, and Austria.

[8][14] In the aftermath, the Western Electric Company provided $100,000 (equivalent to $3.01 million in 2023)[15] to relief and recovery efforts of the family members of the victims.

I didn't believe a huge steamer had done this before my eyes, lashed to a dock, in perfectly calm water, in excellent weather, with no explosion, no fire, nothing.

[citation needed]Carl Sandburg, then known better as a journalist than as a poet, wrote an angry account for The International Socialist Review, accusing regulators of ignoring safety issues and claiming that many of the workers were aboard following company orders for a mandatory staged picnic.

[23] During hearings regarding the extradition of the men to Illinois for trial, principal witness Sidney Jenks, president of the company that built Eastland, testified that her first owners wanted a fast ship to transport fruit, and he designed one capable of reaching 20 mph (32 km/h) and carrying 500 passengers.

"[24] The court refused extradition, holding that the evidence was too weak, with "barely a scintilla of proof" to establish probable cause to find the six guilty.

The court reasoned that the four company officers were not aboard the ship, and that every act charged against the captain and engineer was performed in the ordinary course of business, "more consistent with innocence than with guilt."

The court also reasoned that Eastland "was operated for years and carried thousands safely", and therefore the accused were justified in believing the ship to be seaworthy.

It trained sailors and experienced normal upkeep and repairs until placed in ordinary at Chicago on 9 July 1919, retaining a 10-man caretaker crew aboard.

That assignment continued until the end of World War II in Europe obviated measures to protect transatlantic merchant shipping from German U-boats.

[26] During August 1943, Wilmette transported President Franklin D. Roosevelt, Admiral William D. Leahy, James F. Byrnes and Harry Hopkins[4] on a 10-day fishing vacation in McGregor and Whitefish Bay.

This exhibit would be located along the portion of the Chicago Riverwalk adjacent to the site of the disaster and is planned to consist of panels with text and images.