This town is named after the location, or the location is named after the town. Mud Chicken would enjoy this spot on a Chicago-bound line-they had to build a bridge 3 times to get it right![;)] Where is it?
Council Bluffs, Iowa, has had three bridges (on the UP, as well as one independent bridge that IC later acquired.) But there are other midwestern locations that probably fit the bill, too.
On the other hand, you said “Chicago-bound railroad,” and since all midwestern railroads save one built away from Chicago, that rules out UP. The exception is Santa Fe, which after building westward from Atchison, Kansas, turned around and built east from Kansas City to Chicago.
If we’re talking Milwaukee Road, it crossed the Missouri at Kansas City, Council Bluffs (via trackage rights on UP), Chamberlain, and Mobridge. Only Mobridge meets the criteria of “being named for a place.” But I would not characterize Milwaukee Road as “Chicago-bound,” at Mobridge one would, I think, commonly say it was “Seattle-bound.”
Definately Mobridge- the third bridge was built in 1961 with the creation of Lake Oahe, necessitating the relocation of quite a bit of the transcon MILW main west of town. It was one of five large bridges in the midwest that the US Government built for the MILW from 1945-72 for Army Corps of Engineers dam and waterway projects- can anyone name the other four?