The earliest crossing near West Lake Street was a ferry started in 1829. This ferry had an official operator until about 1832. It wasn't until 1853 that the first bridge, a floating bridge, was constructed at this site. In keeping with the evolution of bridges in Chicago, this floating bridge was replaced by a series of two center pier swing bridges. The second of which was built in 1886. In 1893 the elevated train line was added to the Lake Street bridge.

Bridge tender houses are placed on the northeast and northwest corners of the bridge. The ornamentation on the bridge tender houses is similar to other bridges influenced by Edward Bennett.

The current West Lake Street bridge was the first double deck bascule bridge built over the Chicago River. Train tracks occupy the upper deck while a roadway and sidewalks occupy the lower deck.

Interruption in the train traffic was a major concern for the city designers when this bridge was constructed. T. G. Pihlfeldt devised the construction scheme on this bridge and later improved on it when the North Wells Street bridge was built.

That scheme was to keep the old swing bridge in place while the bascule bridge was built in the open (vertical) position. When the bascule bridge was completed, the old swing bridge was rotated open, cut up and removed via the river and the bascule bridge was lowered. The upper deck was then installed producing only a one week break in rail service. This was considered a major success at the time.