any trip ideas (from Portland or Seattle to Chicago)

hello im looking to travel from either portland or seattle to chicago and i was wondering about the best time to leave in terms of pricing? And any other helpful ideas for this trip will be very appriecated

There aren't any real "best times" when it comes to pricing. However for optimal on time performance and views, I would recommend going in the summer. I would also recommend Portland over Seattle, since you get the Sightseer Lounge west of Spokane, offering phenomenal views of the Columbia River.

Do you know whether you'll be traveling in coach or sleeper?

I have found west coast to Chicago trips best booked in Dec-Jan for a summer trip. I do it every year. Lowest pricing. I booked a bedroom from Sea to Chi leaving Aug 31 for $763.00 on January 8. A seriously good price.

I highly recommend looking at fares that are around five months out. It's very common for them to drop to low bucket at that point.

That works on some trains yes.Never found it much on the west coast trips to CHI.  I am waiting on the CL for Sept 4 but nothing yet.

Sauve850 said:

I have found west coast to Chicago trips best booked in Dec-Jan for a summer trip. I do it every year. Lowest pricing. I booked a bedroom from Sea to Chi leaving Aug 31 for $763.00 on January 8. A seriously good price.

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Seriously good price is putting it mildly! I was curious and just did a search on Amsnag, this is what is showing now, about 2 months after you booked:

Ronbo said:

Sauve850 said:

I have found west coast to Chicago trips best booked in Dec-Jan for a summer trip. I do it every year. Lowest pricing. I booked a bedroom from Sea to Chi leaving Aug 31 for $763.00 on January 8. A seriously good price.

Click to expand...

Seriously good price is putting it mildly! I was curious and just did a search on Amsnag, this is what is showing now, about 2 months after you booked:

View attachment 12718

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Considering 8/27 is listed right there as $763 as well, finding that deal doesn’t seem to be too much of a miracle. Yes it’s the lowest bucket, but that doesn’t mean it’s a rare occurrence. But considering that’s more than five months out, I guess the EB is one of the routes that doesn’t follow the five month rule. That means that in this case, the earlier you book, the better.

While the views from the Sightseer Lounge coming out of Portland are breathtaking, I also enjoy cruising along Puget sound and viewing the Cascades from the Dining Car when departing from Seattle.  I would say it's six of one and a half-dozen of the other, and suggest to make plans based on other factors (eg., which city would you rather visit?). 

Regarding when to book, I think it's best to reserve as early as possible then watch for fare reductions and if that happens, get a refund.

cpotisch said:

Considering 8/27 is listed right there as $763 as well, finding that deal doesn’t seem to be too much of a miracle. Yes it’s the lowest bucket, but that doesn’t mean it’s a rare occurrence. But considering that’s more than five months out, I guess the EB is one of the routes that doesn’t follow the five month rule. That means that in this case, the earlier you book, the better.

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Ive been doing this every summer for a long time. Miracle? No. It is a bit rare to get that kind of rate on west coast trains this time of year. You can check the prime summer months of July thru August on the EB, CZ and SWC and see how many days you can find a rate like that.