The North Wabash Avenue Bridge connected Wabash Avenue on the south bank to Cass Street (now Wabash Ave) on the north bank. The two streets met on a diagonal line across the river. Shipping interests pressured the permitting agency to maintain a wide channel at this location. As a result this bridge has the longest clear span of any of the bridges.

Bridge tender houses are on the SW and NW corners of the bridge. This bridge was an AISC award winner when it was built.

In 1986, the bridge was renamed the Irv Kupcinet bridge. “Kup's Column” ran for almost sixty years in the Chicago Sun-Times. The Sun-Times building was located near the northeast corner of the bridge (now the Trump tower location). Kup said he “walked across the bridge at least 10,000 times.”