What's a good 2-zone trip from/to Chicago

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What would you suggest to maximize scenery and time on train for a 2-zone trip from Chicago? I have done the Zephyr eastbound and Empire Builder Westbound, but am open to doing them again.

My friend and I will purchase one-way air fare from our destination/origin to Chicago.
 
What would you suggest to maximize scenery and time on train for a 2-zone trip from Chicago? I have done the Zephyr eastbound and Empire Builder Westbound, but am open to doing them again.
My friend and I will purchase one-way air fare from our destination/origin to Chicago.
Just got done reading the other recent topic, "Best Way to Spend 20,000 points" . I think Slidell, Louisiana to LAX would be too long a trip for us. How about Chicago to San Diego, can that be done through Portland?
 
The easiest way to check is to plug a pair into the reservations page on the Amtrak website and see what it spits out.
 
Just got done reading the other recent topic, "Best Way to Spend 20,000 points" . I think Slidell, Louisiana to LAX would be too long a trip for us. How about Chicago to San Diego, can that be done through Portland?
No. You can't manipulate your itinerary using multi-leg trips. You'll have to just plug in city pairs and see what you can get on a single booking.

If you start in Milwaukee, you can book an itinerary from there to SAN via Portland for over 77 hours of onboard time!
 
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You dont have to start in Milwaukee to go to LAX via PDX.

I just booked a 20,000AGR 2-zone trip from Chicago to Van Nuys, CA (just north of LA near where my friend lives) via Portland... for early March.

The operator sorta thinks you're strange you want to spend an extra 36 hours on the train and will route you on the SWC... until you say, "Hey, can't I go through Portland"?

But it's worth it -- an extra night on the train.

So I'm out on 27 CHI-PDX and then 11 from PDX-VNC.

3 nights... part of 4 days... 9 meals... 3 breakfasts, 2 lunches, 4 dinners
 
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When I booked my recent trip, I was offered CHI to SJC via LAX or PDX (for the extra night). The AGR rep obviously knew that via PDX would be the preferred route.
 
The easiest way to check is to plug a pair into the reservations page on the Amtrak website and see what it spits out.
Often Amtrak.com will give several options to get from A to B. Does that mean I could use anyone for my Guest reward trip or just the first one that comes up?
 
Often Amtrak.com will give several options to get from A to B. Does that mean I could use anyone for my Guest reward trip or just the first one that comes up?
You can choose any routing shown on amtrak.com - either if you are paying for the trip or getting an AGR award! :D It's just like when one choice includes a bus ride, or another involves getting in later by staying on the train. (Example CS to LAX by staying on the CS or going to BFD and bussing to LAX.)

So choose the longest one, if you want more train time! ;)
 
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