Non-Connected Reservations (points/cash)

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Service Attendant
Jun 29, 2021
Do I need to worry? I was told I can't mix points with cash in booking Amtrak. So, I booked CLE - CHI in coach for my wife and myself with points. It will arrive in CHI at 845am. I also booked CHI - SAS bedroom with a credit card which departs at 145pm same day. Thats a 5-hour layover. Do I need to worry about missing the connection because they are separate reservations? Im asking all you frequent riders because you will know more than anyone about the westbound 29 Capitol Limited and its on time performance.
Yes, you do have to worry.

If 29 is late, you will not automatically be taken care of under Amtrak's Guaranteed Connection policy since the two legs are not under the same reservation and so you will not be flagged as passengers needing reaccomodation.

"Linking" separate reservations just consists of a manual note. Hopefully when you made both reservations at the same time with an AGR agent, they made such a note. The existence of such a note will make it easier for you to prove to Amtrak that you are entitled to connection guarantee protections so they can unwind the automatic consequences for being a "no show", like having all value stripped from your unused Eagle reservation, and get you reaccommodated. It will be a hassle at a stressful time, but such a note will improve your chances of winning.

As to gauging the odds, take @AmtrakBlue's advice on using ASMAD.