The Best place to start is a site called Railjobs .. And to connect and make friends with other railroaders employed in those areas they will usually help guide a person to how they can get a job. But if he a serious about long term Railroading he may want to think about going to College to Major in Railroad Sciences.. If he is close to Wisconsin... Wisconsin Southern Railroad company is a good road to work for.. but there are no openings on their site at the moment. ... Union Pacific .
Is in the area.. What I recommend to do is to Look around for all the railroad companies in the area, and apply to each of them... Join Railroad enthusiasts clubs.. and if he wants to .. He could possibly think about Joining a Railroad Union ... Brotherhood of Railway carmen or something like that.. I am more familar with the Brotherhood of locomotive engineers and trainmen groups.. I have never worked for the railroad I am just a big railfan, but others I have talked to about this said they got in....without problem. If he is willing to relocate CSX and Norfolk Southern both seem to always have openings.. Maybe they have openings in Chicago area.. I know in my area if Wisconsin Union Pacific and Wisconsin Southern Railroad is the only options I tried. UP never got back to me, and WSOR has numerous times.. I am sure you can email the BLE to guide you to the right sources and help too.
Good luck! And keep us posted!
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