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Any tips for airplane-based commuting?

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Old Jun 19, 2025 | 12:47 pm
  #1  
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Any tips for airplane-based commuting?

Hi all,

I live in Portland, OR, and am considering taking a job in the SF Bay Area that would require me to be in the office two days per week. So I'm thinking about renting a room down there and commuting weekly by plane (on my own dime).

Does anyone have any tips for this kind of situation? Whatever can make the process easier/cheaper/less time consuming.

Thank you!
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Old Jun 19, 2025 | 4:20 pm
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Originally Posted by turing
Hi all,

I live in Portland, OR, and am considering taking a job in the SF Bay Area that would require me to be in the office two days per week. So I'm thinking about renting a room down there and commuting weekly by plane (on my own dime).

Does anyone have any tips for this kind of situation? Whatever can make the process easier/cheaper/less time consuming.

Thank you!
Make sure the employer is OK with this situation. If you're two days are consecutive it could work. But, and this is a big but, what happens when there are airline issues and you can't make it in for those two office days? Bad weather, irregular ops, etc. Chances are you will need to fly in the day before and then try and fly back after work the second day. Renting a room could work or even find a close hotel and do a deal with the manager for two nights a week.

I say make sure your employer is good with this because some companies will expect you to be a resident of the state the office is located (if you are required to be in that office). Also you will need to give your home address as Oregon. I know a situation where someone was hired and decided he would do a 2-3 hour one way commute on public transport (train)his 4 days in the office a week. The employer gave him 3 months to relocate as a condition of hire. He decided not to relocate and didn't tell anyone. He got away with it until the winter and the trains started to be delayed and canceled due to weather. He would call off work and finally admitted he was commuting. Employer wasn't happy and made the decision to replace him.

If your employer is good with the situation then go for it. But if you're a direct employee then HR and payroll needs to know.
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Old Jun 19, 2025 | 4:32 pm
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Renting just a room that's not in a hotel sounds grim. Even if it's roughly the same price, hotels have the advantage of providing housekeeping, basic toiletries, maybe breakfast, maybe a F&B outlet, and if it's a chain, points and elite status credit. You can switch hotels for variety or try to negotiate a deal with one. Look also at the cost of booking a long term stay in an extended stay property. In most jurisdictions, if you stay 30 days in the same hotel room, it becomes exempt from state and local taxes.
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Old Jun 19, 2025 | 6:32 pm
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There’s a great TR of a student in La who went to ucb or sfsu or somewhere by plane. Built up his AS status in the process. Indeed a hotel will probably be better than the occasional unknowns of couch surfing.
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Old Jun 23, 2025 | 7:26 pm
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Originally Posted by gaobest
There’s a great TR of a student in La who went to ucb or sfsu or somewhere by plane. Built up his AS status in the process. Indeed a hotel will probably be better than the occasional unknowns of couch surfing.
A thread I enjoyed immensely. Wonder what 985X is up to these days?

Epic commute: I go to school by plane (Aug 2022-May 2023)

Edit: Found the answer. 985X is still in the air!
https://www.flyertalk.com/forum/alas...2025-a-11.html
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Last edited by theshaun; Jun 23, 2025 at 7:32 pm
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Old Jun 23, 2025 | 11:25 pm
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Originally Posted by gaobest
Theres a great TR of a student in La who went to ucb or sfsu or somewhere by plane. Built up his AS status in the process. Indeed a hotel will probably be better than the occasional unknowns of couch surfing.
My older son got his MBA from the University of Chicago, an on-campus program, while working in New York City. They scheduled three-hour classes on Saturday mornings and afternoons. There was so much demand that they ran two vans in from ORD in time to take a morning class and back after the afternoon period. He picked up enough FF miles to take him and his bride to South Africa in J for their honeymoon.
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Old Jun 23, 2025 | 11:29 pm
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Originally Posted by MSPeconomist
Renting just a room that's not in a hotel sounds grim. Even if it's roughly the same price, hotels have the advantage of providing housekeeping, basic toiletries, maybe breakfast, maybe a F&B outlet, and if it's a chain, points and elite status credit. You can switch hotels for variety or try to negotiate a deal with one. Look also at the cost of booking a long term stay in an extended stay property. In most jurisdictions, if you stay 30 days in the same hotel room, it becomes exempt from state and local taxes.
A colleague of mine stayed in a hotel a lot at one point. When he wasn't there, they kept him on the books with no assigned room (or maybe a made-up room #, I don't recall) for a few dollars a day, so his stay would be continuous and the tax-exemption clock wouldn't restart. I think they also let him keep his stuff somewhere, though he might have used his office for that.
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Old Jun 24, 2025 | 5:27 am
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Are the costs in your favor? I roughly estimate weekly:
  • $100 avg. flight ticket round trip (hopefully, if well in advance)
  • $100 rental car + gas (or Ubers), unless you can Bart/Caltrain somewhere closer
  • $200 hotel night for 1 night (hotels around there are expensive and crappy, or where will you find a short term room for less than this)
Or is it about continuing to live in Portland?
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Old Jun 24, 2025 | 1:49 pm
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Originally Posted by Efrem
My older son got his MBA from the University of Chicago, an on-campus program, while working in New York City. They scheduled three-hour classes on Saturday mornings and afternoons. There was so much demand that they ran two vans in from ORD in time to take a morning class and back after the afternoon period. He picked up enough FF miles to take him and his bride to South Africa in J for their honeymoon.
This sounds like an Executive MBA program oriented toward somewhat older (or at least more experienced) MBA students with full time jobs, although some of these programs only require presence on campus about once a month (typically for a weekend). [Obviously the business school at Chicago is excellent, so congrats to your son.]
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Old Jun 25, 2025 | 6:15 am
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One tip is to consider nesting flights. If you plan well in advance, this may be less of an issue, but on shorter notice, something like Monday night out, Wednesday night return itineraries can be costly. You could, for example, buy the following:

Flight 1:
PDX-SFO Monday week 1
SFO-PDX Wednesday week 2

Flight 2:
SFO-PDX Wednesday week 1
PDX-SFO Monday week 2

That way, both trips include a weekend stay. Not sure if this makes as big of a fare difference as it did 20 years ago, but worth researching. You'd generally have to do Flight 1 and Flight 2 on two different airlines if you'd run afoul of Saturday-night stay restrictions, but if this is a long-term plan, you could build up status on two airlines, if there are two carriers that make the trip round-trip, e.g., United and Alaska, which are good complementary programs. There are advantages and disadvantages of this strategy.
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Old Jun 26, 2025 | 1:34 pm
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The biggest challenge will be delays coming in. Unless there's lots of flexibility from the employer the OP would need to fly in two nights before if he/she can't fly during the workday when they would need to be available. Flying out the night before has a risk of a cancellation. At least it would be a quick flight with probably presumably decent options. (Beyond AS and UA).
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Old Jun 30, 2025 | 12:41 am
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Many people underestimate how draining this type of thing can be. Flying is tedious and tiring. It may be fine for a few months, but it can quickly wear you down after that. It would be one thing if this is a short-term arrangement, but if it's open-ended, I would be very hesitant.

Is it possible to ask the employer to rearrange the schedule? For example, instead of being in the office 2 days a week, can you do 4 days in alternate weeks?
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Old Jun 30, 2025 | 12:37 pm
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Originally Posted by mecabq
One tip is to consider nesting flights.
You can do it on a single airline if you nest round trips within one-ways e.g.

Flight 1:
PDX-SFO Monday Week 1 (one-way)

Flight 2:
SFO-PDX Wed Week 1, return PDX-SOF Mon Week 2

Flight x:
SFO-PDX Wed Week n, return PDX-SFO Mon Week n+1

Flight y:
SFO-PDX final flight home, end of engagement.

I did this for some long term contracts in the past to get the saturday night stays in. It's not nesting because you've got a 1-way, then treat your "remote" airport as your "home" airport.... flying home for the weekend over Sat Night, returning to work the following week.
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Old Jun 30, 2025 | 2:41 pm
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Originally Posted by holland
You can do it on a single airline if you nest round trips within one-ways e.g.

Flight 1:
PDX-SFO Monday Week 1 (one-way)

Flight 2:
SFO-PDX Wed Week 1, return PDX-SOF Mon Week 2

Flight x:
SFO-PDX Wed Week n, return PDX-SFO Mon Week n+1

Flight y:
SFO-PDX final flight home, end of engagement.

I did this for some long term contracts in the past to get the saturday night stays in. It's not nesting because you've got a 1-way, then treat your "remote" airport as your "home" airport.... flying home for the weekend over Sat Night, returning to work the following week.
Is that even necessary on this particular route to get low fares?
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Old Jun 30, 2025 | 2:46 pm
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Originally Posted by guv1976
Is that even necessary on this particular route to get low fares?
Likely not. Are Saturday night stays even a thing anymore? I did this many years ago, when they were.
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