Go to 41.866096° -87.635565° in Google Earth, make sure you have the street view layer enabled. FYI these are the Amtrak Chicago coach yards. Look - they have RAIL VIEW! Street view, but on a train!!! 
Ok, so there are a few catches. There are some railview photos posted there, but they are A) inside of Amtrak cars not on the outside and B) while the photos can be accessed at the Amtrak coach yards when looking at them it is clear that they were definitely taken in other places.
But hey, this looks promising! Maybe rail view is actually in the future!!!