Wise or not, there are other things to look at than the ease of getting the trains to the train stations. Such as who owns the station, Chicago’s Union Station is owned by Amtrak, so of course it desires to send its’ trains there. New York’s Pennsylvania Station and Washington’s Union Station are also owned by Amtrak, guess where all its’ trains go?
America is not Europe where just about everything associated with surface transportation is owned by the national government or its’ agencies. In Europe even the freight trains and their steel tracks are owned by the national government, not so in America. Most of the steel rails in America are owned by private companies. The tracks are not ran specifically to get passenger trains to stations, they are ran to get freight trains to depots or freight yards. Any access to train stations is extra as far as the freight train companies are concerned. So it should not be surprising that passenger trains take unique routes to get to train stations.