Thrill of Booking Award Tickets - The Rules

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As I have mentioned in Part 1 of this mini series, I get a kick out of booking award tickets. To recap - I amass quite a bit of airline frequent flier bonuses by using my credit wisely (see Free Eurotrip for my Parents) and when it comes to redeeming those miles for free flights, I try to squeeze as much value out of them as I can. As an aviation geek, I love flying on different aircraft and different airlines. As a traveler, I love being able to use some little known tricks to drastically increase the number of cities I can explore in addition to my actual destination. As a very tall guy, I love the extra space and amenities of the modern business class travel. Combining all of these is not trivial by any means and a few people have recently asked me how am I able to pull these off. In this part of the mini series, I will go over the basics of booking an award ticket with United Airlines. Knowing these rules, I will show you how I normally search and book the flights. Then next week, armed with rules and techniques, I will walk you through how I used this knowledge (and lots of persistence) to put together my latest masterpiece itinerary - a round trip to Europe that will allow me to attend Chris Guillebeau's End of the World party, hop through the Norwegian Arctic including visiting the north-most city on the planet, thaw out while spending some time with my parents in the Mediterranean, and then attend a travel blogger conference in Toronto on the way back. All of that squeezed into an itinerary priced as a simple round trip ticket!

Tulsa - Chicago - Toronto - Dusseldorf - Munich - Oslo - Tromso - Longyearbyen - Tromso - Trondheim - Bergen, Barcelona - Lisbon - Newark - Toronto, Toronto - Chicago -Tulsa

United Airlines Award Travel 101

Before I start describing how I was able to set up this itinerary, it would be helpful to mention some of the rules for award travel when booking through United Airlines:

  • Round trip ticket between US and Europe costs 60,000 miles in Economy and 100,000 miles in Business (these are the cheapest 'Saver' awards)
  • Flights can be operated by United as well as other Star Alliance carriers (Air Canada, Lufthansa, Scandinavian SAS, TAP Portugal, and so on)
  • Round trip itinerary may contain a destination and a stopover (essentially, two destinations)
  • Round trip itinerary may contain a single open jaw (flying into one city, flying out another one)
  • Round trip itinerary may contain up to 16 flights (actual limit depends on the routing)
  • Stops less than 24 hours between connecting flights are not considered destinations
  • Itineraries that contain more than ten flights must be priced manually by an agent (more on that later)

Star Alliance is by far the largest airline alliance in the world (other two being OneWorld and Sky Team) and United website allows searching award seats on almost all of Star Alliance members, making it much easier to look for available seats online.

Now let's look at a few examples to illustrate the rules above.

Destinations, Stopovers, and Open Jaws

Terms 'stopover' and 'destination' are sometimes used interchangeably and could be confusing. Heck, many of the United reservation agents misread the award rules because of this. Essentially, they are the same thing - stops on your itinerary that are longer than 24 hours. What makes things confusing is the fact that stops between connecting flights are sometimes called stopovers as well and the distinction is very important when booking with United.

So, I will not use the term 'stopover' - you either have a destination (stop more than 24 hours) or a connection (stop less than 24 hours). A round trip ticket to Europe allows to have not one, but two destinations!

A round trip ticket also allows to have an open jaw - flying into one city and flying out of another one (you get between the two on your own). So essentially, a round trip ticket now turns into a ticket that allows you to visit (and spend as much time as you want) in three different cities instead of just one!

Let's see how this works:

A traditional round-trip between Origin and Destination

A valid "round-trip" itinerary for a United award - origin and three destinations with an open jaw between two of them. Cost: same as above!

More Stops with Connections

As I have mentioned, I will refer to stops with less than 24 hours between flights as connections. It is normal to have connections in your itinerary when you change planes. What is not normal is to intentionally space out the flights as much apart as possible (but less than 24 hours) to essentially get more free stops on the way!

Yes, one day is not an ideal time frame to visit any city, BUT I think it is a pretty darn good deal compared to the other alternative - not visiting at all. Especially when it does not cost you anything! (except for a few extra $ in taxes)

Here is an example of the trip I set up for my sister last fall:

Regular plane changes in Newark (C) and Frankfurt (C) and one-day connections in Prague (S1) and Munich (C2)

Her original destination was Kiev with simple plane changes in Frankfurt along the way. I reworked her itinerary to get her almost 24 hours in Prague and Munich and added an open jaw between Paris and London so she could spend a few days exploring each.

I have used this little known rule to spend a day in Cairo, Dubai, Seoul, Panama City, Vienna and Istanbul. Was one day enough to check out those places? Aside of Cairo - definitely not! But I am still glad I did it because otherwise I would not have visited them at all!

It is worthy to note here that it gets tricky to set up many one-day connections in a row because the time between the flights must be less than 24 hours, but still enough for you to explore the city and sometimes there are only a few flight options to fly in/out. This is usually the hardest part to line everything up!

Flying Business Class

There is really nothing special about booking Business class itineraries - all same rules apply. The only real difference is the fact that there are even less Business class seats available to be booked using miles so it can get tricky to find availability. I would also like to clarify straight away that I do not care much for flying Business class itself - I have flown on private jets before, so I do not find Business class all that exciting. However, being 6'8" (2.04m) I really do appreciate the legroom on the long haul flights so I am willing to throw in some extra miles and effort for that!

I enjoy my legroom in Business class!

Wrap Up

So hopefully I was able to explain the rules that I use to my advantage when booking some crazy award travel itineraries. In the post tomorrow, I will walk you through how I actually booked my trip to Europe for this spring while taking advantage of all of the above. Here is how my itinerary looks when put in terms I have discussed in this post:

My itinerary "deciphered" - destinations in Bergen, Barcelona and Toronto with connections in Oslo, Tromso, Trondheim, and Lisbon

So I have a few regular connections (C) where I just change planes and five where I will actually have almost 24 hours to explore the city (Oslo, Tromso twice, Trondheim, and Lisbon), three destinations (Bergen, Barcelona and Toronto on the way back) and one Something Else (I will cover that later).

Now that you know the theory, stay tuned to see how it works!

[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