We Flew From Portland to Boston for only 5,000 Alaska Miles and Were Upgraded to First Class – Trick

What is better than flying across the country in first class for 5,000 miles one-way? Hmm, not much comes to mind.



Alaska Airlines has a loophole that allows you to layover in a city that a ticketing system would never allow. We booked Portland, Oregon to San Francisco, seems like a quick 90 minute flight, right?

What I actually did is force a multi-city “layover” in Boston, MA. That is certainly not the most direct routing to get from Portland to San Francisco. Not the point.



On www.alaskaair.com you will start by clicking ‘all search options’. Now choose ‘multi-city’ and ‘use miles’. The goal here is to layover in the city you actually want to visit.


Multi-city routing setup (dates cannot be more than one day apart)


Example: SFO > JFK > then input JFK > PDX, it will show trips from only 5,000 miles. Your layover is JFK which would cost 12,500 miles if booked direct as SFO to JFK.

By mixing a Virgin America and Alaska Airlines flight, Alaska Airlines calculates the award cost from San Francisco to Portland regardless of your layover city. Note, you cannot layover for more than a day, it will register as two flights and not calculate at 5,000 miles.


SFO > JFK > PDX – If you only use the SFO to JFK leg you are saving 7,500 miles



To maximize this trick you will want to fly coast to coast. Alaska Airlines lists flights under 700 flight miles at 5,000 award miles one-way. In order to make this work you will want your first and last airport to be no further than 700 miles apart. You could use, for example, SEA > SFO or SJC > LAX.

Remember, you have to incorporate at least one Virgin America flight in your routing. Virgin’s two main hubs are SFO and LAX, so it will be best to plug-in one of those cities to get this setup properly.


Alaska and Virgin’s route map


To increase your chance of finding award space with this trick, make sure to use city based codes when searching; Bay Area, Los Angeles Area, NYC, WAS, Miami Area, etc.

Hidden City:

Since you will technically be flying hidden city, you will need to pay attention to two important things;

1. Do not check luggage, it will be checked to your final destination, not your layover or “hidden” city.
2. It is possible the airline won’t like this booking trick, so I don’t recommend calling and bringing it to their attention for any reason.


First Class Upgrade:

We booked PDX to BOS to SFO, the first leg on Alaska and the second leg on Virgin America. Our red-eye from Portland to Boston had many first class upgrades available so Alyssa and I were both moved to the front of the plane.

Alyssa earned Alaska’s highest MVP Gold 75k status by matching from Southwest Companion Pass, the details outlined here. Sending one email to Alaska earned her 75k status which entitles her to available upgrades at 120 hours before departure. Upgrades work on cash AND award tickets! 75k status will also upgrade one traveling companion, me in this case, to first class at the same 120 hours window, space permitting.


Finding upgrade space on Alaska Airlines – Expert Flyer


You can search for U class upgrade space using Expert Flyer. If you don’t want to pay for Expert Flyer, you can start a 7 day trial or just look at the Alaska Airlines first class seat map for an estimate of available seats. (though some seats are held for sale at the gate)



You can bet we were crazy enough to fly from Portland to Boston for 13 hours on the ground and turn around on Virgin America to San Francisco. A first class red-eye to Boston went by in a flash, I slept from takeoff to touchdown.

For the return on Virgin America we were both upgraded to Main Cabin Select. Our upgrade earned us complimentary food, premium drinks, 38″ of seat pitch, priority boarding, baggage etc.


Virgin Main Cabin Select – 38″ of seat pitch


Alaska Gold and 75k flyers can earn complimentary upgrades to Virgin Main Cabin Select 24 hours before departure. MVP members clear at 12 hours. What I found strange is that our upgrade didn’t clear 24 hours out even though there was space.

Eventually I had to go to the counter and ‘make’ them put us on the priority list which they said won’t clear until 30 minutes before departure. I think they have some kinks to work out with Alaska status on Virgin.

Are you going to try a 5,000 mile flight from coast to coast using this trick?



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