Empire Builder (to Seattle/flight same day?)

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We are looking to do a cruise out Seward, AK and  are wanting to take the Empire Builder from Chicago to Seattle then fly to Anchorage.  Can I feasibly book a flight out of Seattle at 5:30 PM when the train is scheduled to arrive at 10:25 AM?
 
I really wouldn't count on it. The EB has been so late that I wouldn't feel comfortable spending any less than 12 hours in Seattle.
 
Having a day in Seattle would be the best scenario. But if that day isn’t in the cards and you experienced a large delay, you would have an option of hopping off in Spokane and grabbing a flight to SeaTac. I did a quick check for flights tomorrow and $199/person seems to be the last minute coach fare. But if you’re at least close to ontime in Spokane then I’d be comfortable riding into Seattle with that connection. 
 
Looking at Amtrak's train status page, train number 8 has arrived in Seattle on time and even early over the last three days. Winter weather on the Northern Plains can play Havoc with the schedule and having an extra day in Seattle might be your best bet. If you're going to try to make travel on the same day, be sure to have travel insurance to cover the cost of your flights if you are delayed.
 
I've done some same day flight connections when arriving on Amtrak, and so far it has worked out for the most part, but I would not recommend such action unless you can afford to miss the connection.  The travel insurance Amtrak sells is useless for this sort of thing and even if you have better insurance elsewhere it may not be applicable.  If things go South you may need to eat the cost of a long distance taxi along with a last minute airline ticket.  Whenever possible I book Amtrak-to-airline trips with overnight stopovers for this reason.
 
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The light rail runs every 10 minutes or so from the International District/Chinatown stop (a block from King Street station) to the airport, and takes about 35 minutes. Given that, a four-hour delay is the maximum delay that you could make and still comfortably make your flight. There's 18 days over the past 365 days (or about 5% of arrivals) where there was a greater than 4 hour delay. Of those, six were arrivals between 2:25 PM and 3:00 PM, which without checked bags would still be fairly comfortable. There's another 3 arrivals in the 3:00 PM - 3:30 PM range (tight but doable with Pre/Clear, Uber/Lyft/taxi, and no checked bags) two more in the 3:30 PM - 4:00 PM range (very tight but might still make it,) and a 4:21 PM arrival (probably not doable, but still technically before departure.) The other six arrivals are after the flight would have departed.

A lot of this would have to do with your risk aversion and what kind of alternative flight times would be available should you miss your 5:30 PM flight. Even with trip insurance that would cover that short of a connection, if there's no other options once you arrive in Seattle to get to Anchorage before your cruise leaves you may have to try to catch the cruise at another port and miss part or all of your cruise. That said, it looks like there's some late-night options on Alaska on certain days (including an 11:30 PM and a 12:40 AM flight some days) that on all but one day over the past year (and only a couple dozen over the past 10 years that I can find data for) would make the connection. 

If the train is severely delayed, you'd feel a lot calmer and less concerned about the delay if you're not worried about making even a late-night flight. I also wouldn't want to have the connection be so tight as to only have one overnight before the cruise after the Seattle arrival; I'd either do two nights in Anchorage or a night in Seattle and a night in Anchorage. If the train is severely delayed and you're having to rebook to the next morning at the last minute, it may be difficult to find availability on the early-morning flights that'd likely be required to make the cruise departure time. Even insurance can only help so much; while they can pay for covered misconnects and delays, if there's no availability in the timeframe you need they can't make that suddenly appear.
 
Never a good idea to book a critical same day connection from any North American long distance train.  You likely would have a non refundable airline ticket and a cruise to make.  Rebooking the flight due to a late train could be difficult and would definitely be expensive.  I would build an overnight layover in Seattle or forgo the Builder.
 
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Or talk with your cruise insurance provider and ask if they would cover a last-minute flight from Spokane if your Empire Builder is excessively delayed at that waypoint.
 
Or talk with your cruise insurance provider and ask if they would cover a last-minute flight from Spokane if your Empire Builder is excessively delayed at that waypoint.
Great advice but that's probably going to be a long and tedious discussion.  I've asked hotels about getting a ride from a train station that's half or even a quarter the distance of their airport shuttle service and they are universally dumbfounded trying to comprehend what on earth I'm talking about. :lol:
 
Thank you all for your suggestions.  We are either going to book a red-eye (11:30pm) or fly out the next morning. Fortunately we have an extra day built into our plans.
 
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