Which way is best way to have business class

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I'd say from Chicago, you get lounge access. But I've never actually been on BC outside of the Surfline.
 
Depends on your schedule. If you would use the lounge one way or the other that will make a difference.

If you are boarding en-route it can be nice to just head to BC and find your open seat. Sometimes the corridor trains get a bit crowded in Coach.
 
Run from origination point to/from Chicago on anything with the true single level business class. Yes. Some trains sub/ use a superliner coach sometimes and still sell as business class. If superliner equipment..I would just do from chicago.

I use to take st. Louis-chicago often. Usually biz class is sold out at Springfield heading north, and empty after Springfield when heading south.
 
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