The first bridge at West Washington Boulevard was built in 1891, when the city moved the existing swing bridge at Madison Street to Washington Boulevard. This swing bridge was in use until it was torn down in 1907.

The bridge tender houses are on the SW and NE corners of the bridge.

The first river crossing at West Washington Boulevard was the first vehicular tunnel built in Chicago. This tunnel, completed in 1868, ran between Franklin Street on the east to Clinton Street on the west. On the west side of the river this tunnel was under what is now the Richard V. Ogilvie Transportation Center. It consisted of three passageways – a walkway for pedestrians and two for wagon traffic in both directions. It was a total of 1605 feet long, the original tunnel roof was approximately nineteen feet below the water surface, and the approaches were on a relatively steep ten percent grade.

In the Great Fire of 1871 this tunnel served as an escape route for fleeing the city. The tunnel had a history of impeding river traffic, with an occasional ship grounding on its roof. The tunnel was lowered eight feet and converted to a street car tunnel in 1910. This tunnel was in use until 1953.