
The Greyhound Bus terminal, located at Clark and Randolph, was originally planned to open in the early 1940s. The land was purchased in 1941 for $2,250,000 but World War II interfered with the plans. In 1945, plans were started again in earnest.

It was announced that when the new hub opened both of the Greyhound stops – one a cubbyhole ticket office a mile south of the Loop and a small room on State St. – would close.
The opening was planned for January 1953. However, difficulty obtaining materials and two Greyhound driver strikes delayed the opening until March 19, 1953.
The new station cost more than $10,000,000 and was the Loop’s first multi-million dollar structure in nearly 20 years. The five-story building took up the entire block.
One week before the station opened, a new restaurant attached to the building and fronting Randolph Street had their ribbon cutting ceremony. Toffenetti’s, a Chicago and New York favorite, had leased the space for their newest restaurant.

Toffenetti’s had been a staple of downtown Chicago for 30 years and had several other locations around Chicago. This location was the biggest yet. The new restaurant had a staff of over 250 workers and sat around 600 patrons at a time to handle the 5,000-10,000 people that would be coming through the station at one time. The future of bus travel was bright for Chicago.

The interior of the bus station featured several escalators, an information kiosk, numerous ticket agents and “The Arcade,” which featured 18 shops selling all sorts of wares for the traveler on the way to their next stop.

Throughout the 1950s and early-mid 1960s the Greyhound station was a relatively safe, family friendly station to help get you where you wanted to go. As the late 1960s dawned, the Loop was starting to change. The area had basically become a working area during the day and a place for ne’er-do-wells, addicts and vagrants at night.

By the middle of the 1970s, it had all fallen apart. A scintillating five-page article entitled “The Bus For Rapists, Pickpockets, and Vagrants Is Now Loading” written by Jack Star appeared in the November 23, 1975 issue of The Chicago Tribune.
A couple of years ago, when tsk tsking about the Loop and how it “just isn’t safe at night” was at its peak, one of the truly unsafe places downtown was the Greyhound bus station, at Clark and Randolph Streets. It attracted all sorts of undesirables” pimps in search of new girls, pickpickets and purse-snatchers after fast cash, “midnight cowboys” on the prowl for homosexuals, rapists hunting prey, baggage thieves watching for easy pickings, con artists in need of “pigeon drop” victims, bums looking for a place to drink and flop.”
It had actually gotten so bad that a women and children’s safe zone, patrolled by security, had to be established for the comfort and safety of travelers.
The article goes on to state that a new “get tough” policy would be enforced in the station. The policy stated that everyone who entered had to have a ticket or be locked up.
The new plan worked for a while, but by then the place had such a terrible reputation that local Chicagoans mostly avoided the place.
Finally, in 1989 the old junkie haven was torn down in a Lopp revitalization plan. The bus station with a bright future lasted only 36 years.