Great gesture, however I doubt you will get any takers on this idea. Reason being that most here are not willing to risk handing out buddy passes to complete strangers being its risky. If a buddy passer happens to lose it, gets mad about something, the buddy pass giver risks his travel priveledges. Even if you pay for the buddy pass. If its a friend or someone you know and the know the buddy rider, that may be a different story. I would consider greyhounding him from GL Illinois to SD. That's probably the cheapest way. I am not speaking for everyone here but I can feel the negativeness of the buddy pass situation from years of posting here. Most use them for either family members that are not eligible pass riders or friends that they really know.
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