In October 1889, a subsidiary of the Wisconsin Central Railroad began constructing a new passenger terminal at the southwest corner of Harrison and Wells Streets (then called Fifth Avenue) in Chicago, to replace a nearby temporary facility.

The location of this new depot, along the south branch of the Chicago River, was selected to take advantage of the bustling passenger and freight market traveling on nearby Lake Michigan.

Grand Central never became a prominent destination for large numbers of cross-country travelers, nor for the daily waves of commuters from the suburbs, that other Chicago terminals were.

Unfortunately, however, the circuitous trackage leading to the station from the east forced these trains miles out of their way through the industrial southwest and west side of the city (See map to the left).

It operated six trains a day between Grand Central and Chicago Heights, stopping in Blue Island, Harvey, Thornton and Glenwood.

It ran through Forest Park to Elmhurst, Lombard, Glen Ellyn, Gretna (Carol Stream), Ingalton (West Chicago), St. Charles, Wasco, Lily Lake, Virgil, Sycamore, and DeKalb.

The lightly used terminal became even quieter in the years following World War II, with Grand Central serving 26 intercity passenger trains, down from nearly 40 at its busiest.

[20] Due to its small size, its age and perceived obsolescence,[21] Grand Central was the target of a long-term political effort by the city government to encourage consolidation of passenger terminals in the south Loop.

[25] The remaining six Baltimore and Ohio and ex-Pere Marquette trains last used Grand Central Station on November 8, 1969, and were routed into their new terminus at the Chicago and North Western Terminal the following day.

[20][26] Sitting unused, Grand Central Station's value as an architectural and engineering masterpiece was discounted by its railroad owner, who believed the value of the land for urban redevelopment to be quite substantial.

[29][30] In March 2008, CSX – the successor company to the B&O – sold the property to a Skokie, Illinois-based capital group with the intent of redeveloping the site with mixed-use high-rise buildings.

MGLM Architects proposed constructing a new rail station on the site in February 2012 to accommodate high-speed trains between the city core and O'Hare International Airport.

[33] In September 2016, construction began on a new development named Project Riverline; a joint venture between CMK Companies and Lendlease.

[37] Ira J. Bach noted that when the terminal was demolished: "Chicago lost its greatest monument to the institution which had created it: the railroad.

"[38] At the time Grand Central was completed, passenger trains approached the terminal by crossing the Chicago River to the southwest over a bridge between Taylor Street and Roosevelt Road, constructed in 1885.

The new bridge's location (41°51′40″N 87°38′06″W / 41.86098000°N 87.63494400°W / 41.86098000; -87.63494400[40]), about seven blocks south of its previous crossing, exacerbated the circuitous route of the Baltimore & Ohio Chicago Terminal Railroad (B&OCT) trackage leading to Grand Central Station.