Thrill of Booking Award Tickets - Breaking the Rules

This is the last post of the series where I walk you through how exciting it could get when we book an award ticket using airline frequent flier miles. I spelled out why I do it in Part 1, along with some awesome itineraries I have booked before. Part 2 and Part 3 explained the rules and techniques for booking award travel. In Part 4 I invited you to tag along as I searched for and booked my latest ticket to Europe. Then in Part 5 I showed you how I stretched that ticket beyond what even I thought was possible - covering Chris Guillebeau's End of the World Party in Oslo, touring Mediterranean with my parents, visiting TBEX Toronto on the way back and spending a day each in Tromso, Trondheim, Stockholm, and Lisbon. If you followed along, you know that I got all of these flights in Business class for the price of an ordinary round-trip ticket: 100,000 miles and $272 in taxes!

Tulsa - Chicago - Dusseldorf - Munich - Oslo - Tromso - Trondheim - Stockholm - Bergen | Barcelona - Lisbon - Newark - Toronto | Toronto - Chicago - Tulsa. So far so good!

As crazy as it might seem, this routing is actually perfectly within the rules of an award itinerary when booked through United. But this is what separates the men from the boys - I don't just stretch the rules, I outright break them! [insert your favorite the Matrix reference here]


As I was adding the stops in Norway to my itinerary, I remembered about Svalbard Archipelago to the north of the continent. Out of curiosity, I checked to see if there are any airports served by commercial flights up there. There sure was one in Longyearbyen - the north-most city on the planet. That fact along with the reasons I outlined in my Longyearbyen Preview post yesterday, made me wonder if I could tack that onto my itinerary as well.

from Svalbard Blues

It turned out that there are two flights daily to Longyearbyen operated by Norwegian and SAS. The later is a part of Star Alliance so I was able to look for available flights using United's search. Turned out that SAS flight originated from Tromso, flew up there, turned around and flew back in an hour or so.

The Flight Dilemma

Going from Tromso was the good part since I was planning on visiting already as I know two girls that live up there. We met in Cameron Highlands in Malaysia and ended up traveling to Penang, Phuket, and Ko Phi Phi together.

The problem was with the return flight.

As I mentioned already, the plane flew up there, sat on the ground for a bit, then flew back:

SAS flights to and from Longyearbyen

If you recall from the rules, a stop of more than 24 hours is considered as destination on an award ticket. Because of that, if I fly to Longyearbyen at 1:55pm and fly back the next day at 2:45pm, that would be considered a destination and not a connection (which is a stop less than 24 hours). And I have already used up all my destination 'allowances' in Bergen, Barcelona, and Toronto.

Sure I could give one of those up to stop in Longyearbyen, but I did not want to. It would break the rest of my itinerary and severely increase my costs if I had to purchase the rest of the flights I had tacked on already.

Another alternative was to fly up there and then fly back. I would have 50 minutes on the ground, so it would definitely not count as a destination and in theory I would be able to claim that I have been there, but really, that's not all that exciting (and quite a bit of time wasted to fly up there and back). So that was not an option either in my mind.

There was only one thing I left to do...

Breaking the Rules

When I was flying around the world on an award ticket, I ended up bending or breaking the award rules multiple times.

First, the round-the-world rules specify that one cannot fly through any given geographical region twice. In my case, I needed to fly from Australia/New Zealand to South America and there are no Star Alliance flights that could accomplish that. So I had no choice left but to transition through North America on the way there. That was a problem as I flew out of the US so technically, I could not do that. But because there was no other way to accomplish this, the agent was able to make an exception and get me there (Sydney - Seoul - Los Angeles - Chicago - Sao Paulo in a day, anyone?).

Creative way to get to Brazil

That routing also broke another rule - having no more than 16 flights on the itinerary. Somehow, both Los Angeles - Chicago and Chicago - Sao Paulo flights just happened to be on the same flight number (even though it was different airplanes!) so it counted as 16 segments but I had 17 flights, also requiring an agent override.

So I knew that it is possible to break the rules. But I would need one hell of a reason and a willing agent to make that happen.

In this case with Longyearbyen I kind of had a reason - there was no other flights within the 24 hours of me getting there.

Was it a good reason? One could argue that it was not the case. After all, the connections are technically used to connect between flights to a destination and this was not exactly the case - flying Oslo - Tromso - Longyearbyen - Trondheim - Stockholm - Bergen over a few days is not exactly the most direct way to get between Oslo and Bergen, given the fact that there are plenty of, well, direct flights each day.

But it was a reason! I just needed to find someone willing to go along with it.

Fail #1

I called up the Awards Desk and told the agent I wanted to make a change to my itinerary. We added Tromso to Longyearbyen segment. So far so good. And then Longyearbyen back to Tromso. Computer error. Hold. She is looking into it. Hold. Something isn't right.

I decide to help her: It is probably the fact that I will be in Longyearbyen for more than 24 hours and I already have the maximum number of destinations on my itinerary.

It sure is and she can't override the system. Rules are rules.

Thanks for trying!

Fail #2

I decide to wait a little bit as they were busy dealing with rebooking people due to a storm coming through the North East. I also did not want for the next agent to bring up the same itinerary to the same supervisor again (I was not sure if they were getting a supervisor involved, but did not want to risk it).

So I called back late in the evening.

Same story, except the agent caught onto that even before we tried to feed the return leg into the Almighty Computer.

Thanks for trying!

So maybe I should just drop it? Rules are rules and I did not really have a good reason to push for it. It was already past midnight and I was getting ready to go to bed.

I dialed them up but then hung up at the prompt. Why bother? I don't want to beg again just to get rejected.

But what the hell, why not?


I dialed them again and decided to use a slightly different tactic - I told the agent right away that there might be an issue with the change I am trying to make. She seemed to get a bit excited - let's see if we can make it work.

We start adding the flights. Computer barks about Longyearbyen to Tromso leg but the agent is willing to press on.


So another day in Tromso, off to Trondheim after that per my previous itinerary, just shifting it a couple of days back. And the next day onto Stockholm.

But no, can't do! Turns out on that particular day, there is no longer an option for non-stop flight to ARN from TRD. Bummer. Guess I'll just go straight to Bergen.

That works.

Now she needs to negotiate with the Almighty Computer about that return leg from Longyearbyen. I am honest with her - the issue is the more than 24 hour stop there, but there is no other way I could get back with only one flight daily. And I would really like to go there because I used to work on airplanes and that place had some funky things we had to worry about when designing our avionics system to navigate there. So if there is any way....

She gets on board. I am on hold. She's checking with someone. They can't push it through the SAS system and if they try too many times, it may reject all other SAS flights on my itinerary as well (that's something new!). So they are trying something else while I continue to hold. It's been forty minutes since I wanted to go to bed, but it just might be worth it!

She finally comes back and tells me that they managed to make it happen but I would have to call back in the morning for pricing as that team is gone already. I can sure do that.

Good night and thanks for playing along!

Longyearbyen is in, Stockholm is out. A worthy trade!

So I will head out to Oslo for Chris Guillebeau's End of the World party, then make my way to the north-most city in the world. Later on, tour Paris, Rome and Barcelona with my parents, pick up this itinerary in Barcelona, stop for a week or so in Toronto for TBEX and then finally get back. Plus stops to check out Tromso, Trondheim, Bergen, and Lisbon on the way. In Business class.

Too good to be true?

Sure sounds like it. But I just showed you how it can be done. And here is the total damage:

Final pricing from United

Just for kicks and giggles, I just checked the price of a round trip ticket from Tromso to Longyearbyen and back on United website - $428 just for that!

Another case of award hacking complete!

[message type="custom" width="50%" start_color="#fffff7" end_color="#9fc8f4" border="#999999"]Check out other posts in the Award Booking series: