Should I just fly to Chicago via North Asia?

Confession time: I’m not great at planning my travels. Or the way I’d like to look at it, I always have “aspirational” travel plans. I’d hate to lock in a non-refundable domestic ticket when I could potentially have that destination be a stopover on a larger award ticket.

Fast forward to this coming weekend. I’m going to the Chicago Seminar Do, except I haven’t booked my flight yet. Why? Well, because I started looking at tickets about two months ago, and never saw fares below $500 roundtrip, which seemed crazy. So I monitored prices figuring they’d go down eventually, but they haven’t. Now I have a really hard time pulling the trigger on $500 roundtrip tickets, so even a few days out I still haven’t booked my ticket. Prices haven’t actually gone up substantially from there, so I don’t feel like I was necessarily wrong not to pull the trigger yet, but I’m still trying to get creative.

As y’all know US Airways has a promotion right now whereby you can more or less generate miles for 1.1 cents each. US Airways charges 90,000 miles for business class between the US and North Asia, so that’s roughly $1,000 for the miles needed for such a ticket.

So I can either pay ~$600 for a roundtrip ticket between Seattle and Chicago, or go to Asia for ~$1,100 (with taxes) and incorporate a stopover in Chicago. Perhaps it’s time to finally fly the “Dreamliner?”

My other thought is to try and book an American award to Europe via Chicago, but that would require Chicago to be my international gateway, or else I couldn’t have a stopover there. Now Air Berlin does fly to Chicago and I’d actually like to try them out, but they don’t have award space for the dates I need. British Airways is another option that actually is available, but they impose fuel surcharges, and at that point it just seems to make more sense to book a roundtrip flight between Seattle and Chicago.

Guess I should’ve paid a bit more attention in my college economics class when they discussed marginal value and sunk costs or whatever that stuff is… 😉

Anyone have any better ideas?

Filed Under: Advice, Travel
  1. Lucky, you gave me good advice yesterday regarding booking a domestic flight over Thanksgiving from LAX-DFW. Ultimately, I pulled the trigger and paid $600 for well-timed nonstops on Virgin America. Was it painful? Yes. But is the certainty and convenience ultimately worth it? YES. You may as well shell out the $600 if you can afford it, accrue miles and get from Point A to Point B in the most efficient manner possible. Airfare is unpredictable, but peace of mind can be worth it — just make sure you never check the airfares between SEA-ORD again before you fly, or you’ll be cursing yourself if airfare does fall!

  2. Also, what are the loads like for the SEA-ORD flights? Are they full and therefore fares are unlikely to drop? Or are there plenty of seats to sell?

  3. Wow, sometimes you make my head spin. 😉 Is using miles for a domestic trip to Chicago not a viable option?

  4. @ Peter — Well redeeming for a domestic coach award would make me sad, and first class would run me 50,000 miles, which isn’t much of a deal…

  5. If I had the time, I’d certainly do the longer trip. You know you have to pay about $500 to get to Chicago – so for a little over $400 more you could buy enough US miles to go to ORD and someplace in Asia (and no doubt could work in a 24 hour stop elsewhere).

  6. Uhh, yeah, but at 1.1 cpm the cost of a domestic coach award is about half the cost of buying a ticket ($275). Might make you sad, but it would also save you money – IF for some reason you *didn’t* want to fly around the world to get from SEA to ORD!

  7. Buy the US miles. Not only do you get a business class trip to Asia for ~$200 each way, but the domestic flight will be in first class instead of coach. No-brainer!

  8. @Lucky, it looks like United at least has saver availability this week/weekend for domestic first class… yes, it’s 50,000 miles, but considering the same itinerary in *coach* is $969, I’d say that’s a decent ROI.

    Or, you could just pay for a first class ticket, which is a way better value. Not that $1376 is anything to sneeze at, but you get nonstop flights and more than decent MQM earning potential.

  9. @ Jeff — The space I see is in first class and with a connection, so that would get quite pricey in Avios.

  10. You could always try Amtrak using UR points. The Empire Builder is supposed to have lovely views, and it would be a new product to review…

  11. Why not just look for a geographically challenged US Air agent who will let you route to Chicago via Asia? Maybe the same one who let you fly VIE-IST via Tokyo?

  12. I do this all the time. Ordinarily in your situation, I’ve had pretty good luck finding last-miniute nonstop availability to AA hubs using Avios in Economy. I’m assuming you’ve also checked SEA-ORD on AS too? Seems like if you flex some time, you should be able to make it work. Another trick I’ll pull is use a low-cost United Int’l award to Caribbean/C.America (35k), or Peru (40k). If you fly Copa with United Status, there’s an excellent chance of an upgrade and it’s not ‘too long’ of a flight. You can throw the international legs into the future and solve half of your problem. Similarly, if it’s AA/off-peak time you can pull the same trick out of ORD, and throw the second leg into the future so that you can worry about it later. At $500, you could also consider a 25k RT US award (and they have a “medium” level that’s thinkable), as well as a 17k Miles&More one-way Business Class Redemption allowing one-stop (SEA-IAH-ORD on 787). For novelty, I’d consider Amtrak in a little room and all meals included for one direction. Anyway, ZERO chance I’d pay $500 to go to ORD, pretty much ever. I’d much prefer one of these tricks, or going to Asia for $1100.

  13. Or you can just use hidden city ticketing 😉 but with this option you have to literally wait the day before and book it then

  14. @ PrincessBen — And I’d do that why exactly, given that the cheapest fare on them is over $900?

  15. I haven’t looked, but MKE is not terribly far from ORD. I think there are good alternate airports including MKE, MDW, MSN, RFD. Not ideal, and probably not much cheaper last-minute. But transportation between them can be somewhat easy.

  16. Redeeming miles for a domestic flight may be sad, but sometimes paying $275 for the miles and award beats paying ~$500 for one. 😉

    (One note, though- you want to redeem on AV, not US. $75 last-minute fee on US, $25 on AV. ;))

  17. Just based on my own personal curiosity, I am going to repeat wln’s suggestion of Amtrak. However, a 46 hour train ride may not be what you are looking for. However, it is only 20,000 UR points for a roomette.

  18. I love it! Only travel hackers consider flying to Asia to get the most benefit and value for a domestic flight. I can only imagine posting this to the outside world and watching the heads spin. Stay creative!

  19. Seriously–Amtrak? Gheesh…that literally would be One Mile at a Time. (Although just think about how many meals we would get pictures of over 46 hours!) 😉

  20. Less fun that TATL dreamliner, but maybe kickback in Mexico / Caribbean / C. America for a few days? I know it’s not your thing, but it’s a better value than 50k r/t SEA-ORD. For example UA has avail and prices this at 60k:

    SEA-ORD 10/11
    ORD-CUN 10/14
    CUN-IAH-SEA 10/17

  21. Maybe an opportunity to get rid of less desirable miles like SkyPesos? Sometimes DL has good award availability a few days before departure. MKE is only a good option if you are saving so much money that it covers the rental car and fuel.

  22. Of course even as I read what I just wrote, I’m not convinced my suggestion is all that much better than just a r/t.

    How about make it a giveaway/contest with US miles. Transfer 45k+45k bonus miles to one of your friendly blog readers that likely won’t take advantage of their US 25% or 50% award rebate promo. The reader’s account books your flight, you route via N. Asia, and your reader gets 22500 or 30000 miles back…

    And yes, this is an 80% self-serving suggestion. Ok 90%. And requires a ridiculous amount of trust. And probably is my second bad idea of the day. Always happy to help. 🙂

  23. I once flew from FLL to EWR via BRU. That was also a last-minute booking, as I had to cancel my travel from MIA to EWR via NRT due to the earthquake in Japan. (-:

  24. This is why i love southwest rr points because if u book this a month or 2 out u wouldve paid like 15,000 pts and couldve brought a companion for free with the 2 chase cards. I know a swa trip report is not sexy but it can be practicle!

  25. Why not click on your own links and pickup either $800ish Southwest credit and/or 2x Airtrsn R/Ts? Either will get you to MDW multiple times, albeit not in the style your accustomed to.

    And it’s a biz expense anyway if you have to buy it.

  26. And you can write the story about the best way to get there whether you take your own advice or not. It doesn’t matter to us.

  27. I agree $500 mid-con is tough to swallow. I wouldn’t go for it either unless i was billing a client or it was companion pass eligible like on Southwest.

  28. What’s wrong with Ord being your gateway to Europe?

    You could go to Europe in May, get the Sea-Ord for free.

    On the way back, you could book Ord-Sfo-layover -HKG and buy a rt ticket Sfo-sea. Or perhaps all the way to Sri Lanka (still only 67.5k in f on AA/CX).

    Or does that exceed mom

  29. @ Beachfan — Except it’s not really “free” when I’d have to buy a ticket to Chicago in the future to position.

  30. Take the North Asia Excursion! It’ll make for a great trip report and YOU NEED TO GET ON A DREAMLINER!

  31. MKE may not be cheaper, but it’s worth noting that there’s a direct Amtrak connection from there to downtown Chicago. 7 trains a day and about 1:15 to downtown. So not as bad as you might think if you time it right. There’s also a few bus services from MKE to Chicago for $25-30. Same oon the other end. You could do Amtrak to Portland and fly out of there if it happened to be cheaper.

  32. I’m also voting for Amtrak. Do something different!! But you probably ought to get moving ASAP if you need to be in Chicago this weekend. CHOO CHOO!!!

  33. Hey, Lucky, don’t forget about tax deductions. If you value UA miles at 1.8 cents each, then paying 25,000 miles instead of $600 is the better choice for personal expenses, but paying the $600 may be better for business expenses (depending on your tax bracket).

    (Waitaminnit…there’s no state income tax in Washington. So Bellevueites are in the 0% tax bracket. Oh, well.)

  34. I think a genuine trip report on 2V or WN could be a lot of fun, assuming it was handled in an appropriate fashion. Endlessly bashing them because they don’t live up to rosy eyed view of CX/SQ/LH would get really old mighty fast, but a more nuanced review with equal parts wit and honesty could prove interesting and enjoyable. In any case it’d probably be a lot more entertaining than some “because it’s there” report on a middle of nowhere location nobody else cares about like Longyearbyen.

  35. I’m also go to Chicago this weekend. Used AS FF miles plus cash. $169.00 net takes the sting out of it. No chance for upgrade though.

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