Thrill of Booking Award Tickets - My Latest Itinerary

After teasing you with some crazy flight itineraries in Part 1, going over some of the rules for award travel booking in Part 2, and walking you through the techniques I use in Part 3,  today I invite you join me as I was boarding the emotional roller coaster of actually searching for and booking my latest masterpiece itinerary.

Original Goal

At the beginning, there were two things I wanted to accomplish with this itinerary - attend Chris Guillebeau's (The Art of Nonconformity, The $100 Startup) End of the World party in Oslo on April 7. We will be celebrating Chris' accomplishment of visiting every country in the world (he saved Norway for last)! As if that was not exciting enough, I have always wanted to visit Scandinavia so this was a good reason to finally do that.

After Scandinavia, I will spend some time in Europe on my own before meeting up with my parents in May to travel through Paris, Rome and Barcelona with them.

Getting to Oslo

Even though United has direct flights to Oslo and Stockholm, it turned out to be quite and adventure getting there.

I had very tight constrains - the party starts at 7pm on April 7th and I could not leave until April 6th. So I had to cross the Atlantic on the 6th. I started with one way award ticket search between Tulsa and Oslo:

Not looking promising with no availability that whole weekend

Well, the easy way did not work.

As I mentioned before, the hardest part is usually finding availability on transatlantic segment so that's what I tried doing next. Denver, Chicago, Newark, and Washington (United hubs in US) to hubs and major cities in Europe - Frankfurt, Munich (Lufthansa), Zurich (Swiss), Vienna (Austrian), Paris, London, Manchester, Madrid, and Barcelona.

After quite a bit of time searching, I came up with exactly zero options. Seemed like there were just no available business class seats to Europe that weekend. This by itself was very disheartening since there ALWAYS seems to be space as there are a ton of flights especially between Chicago and Munich/Frankfurt. Bummer!

Then I remembered that TAP Portugal is part of Star Alliance so I checked Lisbon. Hurray! I found myself a Business class seat! Next was the search for flights from Lisbon to Oslo and my excitement did not last long - none of the options would get me there before the party. That's another bummer.

Then I kicked myself as I remembered about Air Canada (also a Star Alliance member) and quickly search for flights from their hub in Toronto finding a flight to London on 777-300ER. Their ExecutiveFirst product seemed pretty good, but Heathrow could be a nightmare for connections.

Air Canada flight from Toronto to London Heathrow

I also remembered that Dusseldorf is becoming one of Lufthansa's big focus cities. So after more searching, I had another option - Lufthansa A340-600 flight from Toronto to Dusseldorf:

The only flight options for crossing the pond that weekend

Next, it was time to search for one way availability between London, Dusseldorf and Oslo. Going through London, I could continue through Brussels or Zurich but would be cutting it close. Dusseldorf seemed like the best option as I could connect through Munich and get to Oslo with a few hours to spare before the party.

Dusseldorf to Oslo connecting in Munich

Another benefit of going through Dusseldorf would be avoiding Heathrow (including its hefty fees) but the drawback was having to depart Tulsa for Chicago at 6 am in order to make the Air Canada connection to Toronto. But I would still get there with plenty of time before the party so I had my first (26 hour) leg figured out!

Tulsa - Chicago - Toronto - Dusseldorf - Munich - Oslo. Whew!

Setting Up Return Leg

My parents would be returning from Barcelona so I figured I would see if I could come back with them. A quick one way Barcelona - Tulsa search confirmed that. I was actually surprised to see that all three of us could go Barcelona - Munich - Chicago - Tulsa in Business class since having three seats in Biz on four consecutive flights is not a common occasion. But I wasn't complaining!

Because of the rules that allow for two destinations and an open jaw on the award ticket to Europe (see Part 2), I knew I could also join them on Rome to Barcelona flight connecting through Zurich, so the final itinerary looked like this:

First iteration of the full itinerary

This was a valid routing because my first destination would be Oslo, followed by an open jaw segment, picking up again at Rome. Barcelona would the be second destination.

Booking Over the Phone

As I mentioned in Part 3, as useful as United award search is for looking up these segments, it craps out rather quickly when trying to book something as complex as this so I had to call their Award Desk.

Just as I thought I had it all figured out, for some reason, their computer was not showing availability on Toronto to Dusseldorf leg. I waited in suspense while she was checking things out. I guess I won't be able to avoid Heathrow after all!

The agent came back and (quite rudely) threw me over to the Online Desk because "it [website] shouldn't show things differently from what we have here". Ugh! But at least they didn't say 'no'!

With the Online Desk buried somewhere in India, it took me a while to get the itinerary set up with those guys (but they did find availability on the flights I needed). Not being very up to speed on award rules, they did not sound very optimistic that it would price out. But I kept at it for forty minutes, spoon feeding them all of the dates and flight numbers.

To their amazement (and my amusement with their amazement), it did price out, meaning that it was a valid itinerary. Just as I expected, the total came at 100,000 miles (same price as a regular round trip ticket would cost!) and about $270 in taxes and $25 phone booking fee (I knew I will be able to get rid of that later). Not bad for the all-business class itinerary!

So mission accomplished? Well, far from it actually!

Stretching It Out

So I had both of my goals accomplished - I will leave on April 6, get to Oslo with a few hours to spare before the party, then join my parents on the flights from Rome to Barcelona and then from Barcelona all the way back home. What else could I ask for, right?

Well, as good as it felt to crack this nut, I immediately got the itch - the itch of realizing that while I was taking full advantage of two destinations + open jaw allowance, I was not maximizing the benefit of having up to 15 stops on my itinerary. Sure, I had connections in Chicago, Toronto, Dusseldorf and Munich on the way there and then again Munich and Chicago on the way back, but these were just plain old connections. I was not using any of them to spend the 24 hours in a city to check it out - what a waste!

As I mentioned in Part 2, I love to take advantage of the rule that connections less than 24 hours are not considered destinations and if I can time my flights right, I could spend up to a day in any connecting city. I have used that before to check out CairoDubaiSeoul, Panama City, Vienna and Istanbul essentially for free.


Because I was planning on coming back with my parents, it would not be an option to stop somewhere on the way for a day. So I could only tack on the connections on my Tulsa to Oslo segment. Furthermore, as much as I would of liked to check out Toronto and Dusseldorf on the way, I could not because I had to be in Oslo on the 7th for the party. So the only option was to go somewhere after Oslo.

Where should I go? I decided on Bergen - it is a very scenic city on the west cost of Norway that I planned on visiting anyways. The train ride takes about eight hours and costs over $100 each way, so I figured why not just fly there for "free" the day after the party (remember, if I was to count Oslo as a connecting city, I could not spend more than 24 hours there). I would save time and money getting to Bergen this way, spend a few days there and then take the train back to Oslo to spend more time there.

There were a few flight options that would get me out of Oslo before the 24hr cut off, so I called back to add one of them to my itinerary:

Oslo - Bergen leg added to the itinerary

It took another good thirty minutes on the phone while they were working on pricing the itinerary so I went ahead and asked that the phone booking fee ($25) was waived because of the time I have spent on the phone both times as well as because I was getting the error on the website. The guys obliged so I got myself an extra leg  and $25 less in fees!

This was a good start, but I knew I could do better. And I did! More on that tomorrow.

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


Tips & Tricks, Traveldimaaward