Interesting trivia in the Metra newsletter
The February 2009 issue of On the Bi-Level also includes FAQs on Metra's capital budget (and lack thereof).
Most aspects of Metra's service and operations are logical. I am ignoring the left-handed track side arrangement* for the moment.
But on the UP North Line, why is the first stop after having left the downtown station [Ogilvie Transportation Center] called "Clybourn" when the street by that name is over a half-mile away and Elston and Ashland avenues (neither of which are piddly streets) are just down the stairs?
We get this question every few years. You're right---Clybourn Avenue is a few blocks away from the station. But it didn't used to be. Early Chicago maps show Clybourn ended its northwest diagonal run from Division Street at the point where it meets Racine. It then turned directly west, crossing the river and ending at what [is] now Damen. When in later years the northwest diagonal of Clybourn was extended (eventually to Belmont), the east-west section that crossed the river was renamed Clybourn Place. That section was later given its current name, Cortland Street, after the street that it almost lines up with at Damen.
A 1908 book on place names associated with the old Chicago & North Western railroad says the "Clybourn Junction" station used to be known as Clybourn Place, "from one of the streets of Chicago. ... The word Place was dropped and the word Junction inserted, as it was the junction of two lines of the railroad" (now the UP North and UP Northwest).
However, that book errs when it ways the street was named for settler "Peter" Clybourn. His name was actually Archibald Clybourn, one of early Chicago's most prominent citizens. His family established their homestead and a slaughterhouse (Chicago's first) on the west bank of the river, near what is now the station, in 1824; he lived there until his death in 1872.
*Only what are now the Union Pacific lines, actually. That's 3 of the 11 Metra routes.