Chicago Union Station
Chicago's Union Station opened in 16 May 1925, replacing a station on the same site built in 1881. The Beaux-Arts design was by Daniel Burnham, with completion by Graham, Anderson, Probst and White after Burnham's death. Although construction began in 1913, it was delayed numerous times by World War I and labor issues.
The station opened at the apex of American intercity rail travel, and in a fate similar to that of Penn Station in New York City, Union Station's main concourse was demolished in 1969 and covered with a bland office tower (222 South Riverside), leaving rail passengers to grovel in a claustrophobic basement.
Although the Great Hall waiting room was preserved, the configuration of the new station makes it a largely useless appendage whose primary civic virtue is as an event facility.
The two statues high on the east wall of the Great Hall symbolize the 24-hour nature of passenger railroads. One holds a rooster (Day) and the other an owl (Night).
With the resurgence of passenger rail, the existing concourse is woefully overcrowded. While Amtrak seems to be interested in monetizing the space over the headhouse, the only plans for the concourse appear to be minor tweaks, with little hope or funding for doing something audaciously transformative like demolishing the office building or moving operations to the massive abandoned post office a couple of blocks to the south.
The station has, fittingly been used to promote High-Speed rail efforts in the state, although the station's structure as a double-stub station (with no pass-through) limits its suitability as a HSR station.
A few blocks southwest of Union Station, Tutto Italiano (501 South Wells) has a preserved rail car used as a dining area.
Lou Mitchell's is around the corner on 565 West Jackson Boulevard. Great place for breakfast or lunch if you've got extra time or a layover.
Most of Amtrak's Midwestern routes terminate at Chicago's Union Station, providing a nice view of Chicago's past and current infrastructure along the way.
Periodically, you might see a private rail car attached to the end of an Amtrak train.
The Tioga Pass was built in 1959 for the Mountain Region Vice President of the Canadian National railroad. After a winding journey through dereliction, it ended up as one of a group of vintage cars that can be chartered from L.A. Rail.
3301 Royal Street was a streamline bedroom-buffet-lounge observation car built by Pullman-Standard and delivered in the Spring of 1950. It is operated by American Rail Excursions.
On a less expensive note, the curbside intercity bus company MegaBus has it's "station" on the South Canal Street sidewalk next to the train shed.
Daytime, nighttime, anytime, things go better with rock. (Stephen Plunkett, et al)