Thrill of Booking Award Tickets - Why I Do It

If you know me even just a bit, you are probably aware that I am crazy about three things - aviation, travel and doing both of those in style while paying just a tiny fraction of what it normally costs. I amass thousands of reward points and frequent flier miles through combination of new credit card sign-up bonuses and some creative spending on those cards. And when the time comes to use the miles to book award tickets, it is hard to describe how excited I get. Another batch of cards that have served their purpose

It is a rush to see how much can I stretch those award tickets. A thrill of searching for itineraries that go beyond a simple round trip. An excitement of stuffing so many stops on the itinerary that the airline computers give up trying to price it. Then calling the airline to get it set up manually and hear the agents expressing their excitement or disbelief (usually both) that it is actually valid - it's a change from the mundane for them as well (some are even willing to bend the rules slightly to make it happen)!

My masterpiece - the round-the-world itinerary

My round-the-world itinerary above could of been much duller - after all, technically, only five stops are allowed, but I was able to set up my flights such that I spent almost a day in Cairo, Dubai, Seoul, and Panama City for no extra cost besides a few bucks in additional taxes! In fact, the entire itinerary above only costed me $368 flying in business class!

But that was not even my first "award-hacking" (I should probably trade mark that). I accidently discovered this hobby when I was booking a round trip award flight to Europe in 2009. Cedar Rapids to Amsterdam and back was going to cost me 50,000 Northwest miles. But I wanted to travel in Europe too, so on a whim I tried to price a multistop itinerary:

Adding Paris, Marseille, Milano and connecting through NYC for free!

In the end, I booked the trip to Amsterdam with a flight to Paris and then another flight from Milan back to Amsterdam and a stop in New York City on the way back. All for the same 50,000 miles and extra ~$100 in taxes. There were too many segments for computer to price it so I had to wait for Northwest to manually issue two separate tickets to cover all of these flights.

And I was hooked!

Then this past fall I had the dilemma of trying to get to Kiev from Barcelona and  then later on coming back to Frankfurt. Sure, I could get a round-trip ticket for 25,000 miles - but I also wanted to revisit Oktoberfest in Munich and check out Vienna on the way. After some soul award-searching, I had the ticket booked: Barcelona to Munich, five days for Oktoberfest, Munich to Vienna for a day and then onto Kiev for a couple of months. Later on, I even squeezed in a day stop in Istanbul on the way back to Frankfurt! All that for the same 25,000 miles.

Barcelona - Munich - Vienna - Kiev - Istanbul - Frankfurt

My sister also had to come to Kiev for a couple of weeks, so we booked her a round-trip ticket between San Francisco and Kiev for 60,000 miles. But being the great brother I am (and because this stuff is like crack for me now) I offered her to rework the boring Kiev - Frankfurt - San Francisco return leg into an exciting tour of Europe. In the end, I surprised myself with what I was able to stuff into her itinerary: day stops in Vienna, Prague, and Zurich with a few days in Paris plus more day stops in Munich and London. Once again, all for the same 60,000 United miles!

She was a bit more boring reasonable than I am and opted for less stops and more time in Paris and London. Her final ticket looked like this:

Return leg: "free" stops in Prague, Munich, Paris, and London

So where am I going with all of this? Am I just showing off?

Well, sure, there is some of that :) Who wouldn't want to travel more for the same price?

But beyond showing off, I wanted to show that it is not a just one-time fluke (apparently, there are some people out there that don't think this is actually possible, ahem, Aleksey's coworkers). This can be done again and again for anyone that wants to stretch their award miles to the fullest!

In my next few posts I will show you how crazy and exiting [!] it can get trying to figure out a complex itinerary that still conforms to the rules (even if some agents don't think it does), takes me hopping around frigid Arctic for days, including a visit to the north-most city on the planet, and allows me to hit up multiple events in three separate parts of the world. All for the cost of a round trip ticket!

Europe 2013: End of the World party in Oslo, Arctic hopping, Mediterranean with my parents and TBEX Toronto

And while I am at it, I will also reveal more details about a service I am launching to help others do the same. Frigid Arctic hopping is optional (but highly recommended)!

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

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Tips & Tricks, Traveldimaaward