Getting to Delta’s "best" SkyMiles price

How much is a business class award ticket from Boston to Singapore booked with Delta SkyMiles? The carrier no longer publishes award charts for its loyalty program so that question is mighty hard to answer. Still, it is the route I needed to book and Delta’s SkyTeam (and joint venture) partner Korean Air had the best itinerary available – a single 90 minute connection at Incheon – and so I was destined to find out.

Searching on the Delta website for Boston to Singapore brought up some downright frightening prices. The “Best Match” for my request (Best for whom?!?), according to the airline’s systems, was a 400,000 point trip taking more than 29 hours and including an extra stop in Detroit along the way.

The Detroit airport is pretty nice and the flagship Delta One suite on the A350 is a very nice product. But that price point is most definitely not in my budget.


I switched the sort order to “Price” and a few options showed up at the 135,000 point level, though all of them still included the double connection and the absurdly early departure from Boston.


I know the Korean Air nonstop to Seoul is relatively new (it just started last month) but surely Delta’s computers must know about it, right?? I tested that theory by trying to book just the nonstop to Seoul. The flight showed up and the price was very nice, just 85,000 points for the one way trip in business class.


I’d still need to get to Singapore, so I searched for that segment as well. Multiple options available, again at a reasonable price point (though, surprisingly, there were also connecting partner itineraries available for 5,000 fewer points).


With those two flights both showing availability there must be a way to get that trip booked on the Delta website, right?? Wrong.


I tried multi-city. I tried forcing connections. I tried everything I could think of and came up empty. I now had to throw myself at the mercy of the agents at the call center to see what might come of this effort. The first call did not go well.

Making the call

I explained the trip I wanted to the agent. He didn’t like that I was trying to build my own itinerary rather than accept the options the website spit out for me. He went so far as to accuse me of “Frankensteining” the routings to manipulate the system. He was also none too pleased when I countered that the itinerary I’m shopping is the shortest in distance flown and time en route. I’ve made my share of creative bookings over the years. I know that it shouldn’t take four days to get from Stockholm to Istanbul, for example (that was an awesome trip, FWIW). But this trip is decidedly not that. I’m trying to make things as simple as possible and the SkyMiles system didn’t want that.

After much deliberation and fighting with the system he came back with the price of 130k points, essentially creating an end-on-end itinerary for the trip. That didn’t seem right to me for a partner award so I hung up, figuring I should at least check with FlyingBlue before transferring in my AmEx points to cover the trip.

A pair of calls to FlyingBlue resulted in that program insisting that no business class reward seats were available on the flights, despite the Delta site continuing to show them. Realizing that wouldn’t be a viable option I returned to Delta. I wasn’t happy about paying 130k but the dates and flight times were correct and I have the points. May as well use them, right?

Another phone call and another agent perplexed as to why the BOS-SIN search would not show the flights I was quoting to her. But this agent was not angry with me. She was angry at the computer for not pricing the trip properly. She put me on hold for a few minutes to speak with her supervisor. When she returned to the line I was slightly dumbfounded: It seems there was a way to price the whole trip through at 85k points after all. Needless to say, that ticket is now issued and window seats are secured for the start of a great adventure in Asia this winter.



But could I repeat the performance??

As for a moral of this story, I’m not entirely sure one exists.

Searching individual segments and feeding them to the agents used to be a booking method that worked consistently. Some agents (e.g. the first one I spoke with) won’t process those requests any more, claiming that members are ruining the program for others. At other airlines such requests mostly cannot be priced at all or end up as end-on-end, additive rates. Again, not good for members.

The other age-old adage is HUCA: Hang Up and Call Again. While that did eventually work here I’m not entirely sure it was supposed to. Delta’s policies are spectacularly unclear on the issue and who knows what would really happen next time. On the plus side, it is unlikely that I’d successfully manage to talk to everyone in the call center again like I did once some years ago.

I also feel like there’s a little bit of a victory lap to be taken right now, as this is two different long-haul partner awards in business class I’ve booked with Delta SkyMiles in the past couple weeks, both at very reasonable rates. Sure, they’re not always easy to find, but I got what I needed with only a day or two of flexibility required.

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Seth Miller

I'm Seth, also known as the Wandering Aramean. I was bit by the travel bug 30 years ago and there's no sign of a cure. I fly ~200,000 miles annually; these are my stories. You can connect with me on Twitter, Facebook, and LinkedIn.


    1. Maybe?

      That might have something to do with it, but the many different answers I received makes it hard to tell. Also, I’m surprised an agent would be able to override that so easily, though maybe that’s foolish optimism in their systems work.

  1. If one can get to the CVG call center, they were often very helpful, as are the ones in SLC
    We are all now running out of options for reasonable award flights
    DL is a joke, UA is following shortly, AA I am sure is next and is ruining the options with the ME airlines fight and AS miles are hard to get

  2. I must have missed something. Why can’t you just book the two segments separately?

    1. I was actually wondering the same thing…why not just book two one way segments of the points were more advantageous separately?

      1. Eventually this would’ve been my move. But I also wanted everything on a single PNR to help in case of IROPs to avoid needing to negotiate with the airlines to offer rebooking and other benefits that would be part of the play. Also, this is a trip for someone else (meeting me in SIN; I have a separate ticket to get there) so making it as smooth as possible was part of the goal.

        Even if I did want to book separate reservations Delta didn’t make it clear at all that such was an option until I went digging for it which was a big part of my frustration.

        Finally, the best price did come eventually from the single booking, not from the end-on-end pricing.

        1. No clue what an IROP is. But I’m guessing a big motivation was hoping to get Delta to give you the whole booking at 85k? Without that potential carrot, would’ve seemed much easier to talk to Korean Air at check in.

          1. Irregular operations, like delays, cancellations and such. Linking separate itineraries together isn’t really a thing that works sufficiently consistently for me to want to risk it in this case (though I certainly have often enough).

            And, yes, getting the award priced properly was also a key factor.

    2. I think he got a better rate at 85K total by not booking separately. Also, if he checked a bag, two separate bookings could create delays and inconvenience at the next airport if he’s not able to get the airline to consolidate the bookings. He’d have to go thru customs/immigration to retrieve luggage and re-check it for the next flight.

  3. I had a similar Delta experience on a routing from ATL-MNL. I could book ATL-JFK-TPE (China Airlines) from the website at 85K, but the onward TPE-MNL could not be stitched to the original booking using the site. I also experienced negative attitude from the first Delta rep I spoke to. She told me it wasn’t possible, and couldn’t find the the second segment of my requested itinerary at all. She seemed frustrated at me for asking the question. I eventually hung up, and called again. The second rep was much nicer and way more knowledgeable. He found everything, got it booked and I was on my way.

  4. This was a terrible article…really never explained anything. The only thing I got was hang up and call again.

    1. I think you got the most important part. The skill level of Delta’s award desk seems to be inconsistent from one individual to the next. Even if you know their rules better than they do themselves, in some cases, it won’t help you.

      So yea… hang up and try again.

  5. So, to be clear… you are showing us a screenshot of a one way ticket from Boston to Singapore for 85K miles, yes?

    1. Yes, confirmed in business class (O inventory) for both segments.

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