Roomette and Coach Ticket on Same Trip?

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I am looking for a cost-effective way to take a roomette as a solo traveler. Is it possible for me to purchase a 1 way coach ticket between Chicago and LA (for example) and then to buy a roomette for Kansas City-La Junta and then another roomette for Gallup-LA?

The reason I ask is because of the policy against buying two tickets for one person (if a rider wanted a row to themselves) - I recently read they do not allow that for some reason.
 
That policy refers to two tickets for one person for the same segment. It is OK to combine accommodation types on consecutive segments, for example I've combined a roomette on one segment with a switch to coach on a subsequent segment. You will not buy two tickets for yourself, rather you will buy a multi-city trip with different accommodations on different segments (CHI to Kansas City, coach; Kansas Cty to La Junta, roomette; etc.

You will only be allowed to eat diner meals on your roomette segments. When you change accommodations, you will most likely be asked to alight from the train, walk down the outside, and board as if you were a new passenger. Your new accommodation will be expecting you at your change point.

This may not actually save you much if any money. Check the price both ways before purchasing. The reason is both a question of roomette demand during different segments, and a question of Amtrak having to make up the roomette multiple times.
 
You need to check it both ways. The savings may not be nearly as much as you suppose, and you lose at least some meals, although you could probably get breakfast before La Junta and dinner after Gallup.

You'd book it using Multi-City with 4 segments, CHI-KCY, KCY-LAJ, LAJ-GLP, GLP-LAX.

You are correct in that Amtrak does not allow a passenger to book two coach seats for one person. The system would also ultimately reject two bookings for the same person between the same points on the same day as an "impossible booking". I don't think it does it in real-time, though. With that said, I do not see the relationship between that and what you want to do.
 
Thank you both! Super appreciated. I was thinking about doing this with one of the America the Beautiful passes (10 trips for $500) and using one of those trips for the coach purchases. That said, thanks for the updates about the impossible booking and that you can do the multi-city segments. Super helpful!
 
I used a pass once, and it was a lot of fun. But they didn't allow upgrades to a room. I would check their policies.
 
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