Opened by R.H. Southgate just before the 1893 World’s Fair,[1] the hotel has hosted numerous US Presidents and a wide range of political and cultural events.

Designed by architect Clinton J. Warren, the north tower was linked to the Auditorium building by a marble-lined underground passage called Peacock Alley.

[1] After the World's Columbian Exposition,[6] the hotel underwent two major expansions and renovations, first in 1902 and then again in 1907, which brought the total complex up to 1 million square feet (93,000 m2).

[8] In 1939, tragedy befell the hotel when guest Adele Langer leapt from a thirteenth floor window with her sons, killing all three.

[9] Following the outbreak of World War II, the Government purchased the hotel and used it as a training school for U.S. Army Air Forces.

[15] Roosevelt, who at that time was seeking the Republican nomination for President, spoke from the balcony of his room at the hotel to a crowd assembled across the street in Grant Park.

[18] The hotel has hosted International Mr. Leather guests and festivities every Memorial Day weekend since 2015 (though the contest itself has often been held elsewhere).

[19][20][21] Taos Society of Artists painter, E. Martin Hennings painted the ceiling murals inside the Florentine Room around 1918.

[22] In 1940, Louis Grell (1887–1960), a Chicago-based artist, was commissioned to paint thirteen murals for the lunettes that are an architectural feature surrounding the grand lobby.