Booking A Complex Reward Flight Introduction

It all starts with an idea: ‘It sure would be cool to visit Paris‘ or ‘I wonder what Jakarta traffic is like at the end of January‘ or ‘I have the holiday blues… I think I need to fly somewhere‘. While most people would dismiss those ideas relatively quickly, a travel hacker will naturally pull out all the tools to see how they can turn those thoughts into action – preferably on one award ticket with minimum taxes and fees. This is exactly what happened to me. Paris came to mind as somewhere I’d like to visit, and before I knew it, I was booking a complex reward flight with an open-jaw and stops on three different continents.

A Simple Idea Can Quickly Turn Into This

A Simple Idea Can Quickly Turn Into This

So, what started as a trip to Paris for a couple days ended up being another Aeroplan mini-round-the-world redemption with a stop in Jakarta and and open-jaw in Seattle. The entire redemption cost 155,000 Aeroplan miles and $237 in taxes and fees, in addition to a connection flight on a separate award ticket with Alaska from Seattle to Vancouver. My preferred flight times weren’t available with Air Canada to add to the mini-round-the-world, so I opted instead to use 5,000 Alaska miles and $5.60 in taxes/fees bring me home at the end of my journey.

I wanted to share some basic insight into the madness behind booking a complex reward flight, and outline the steps and thought process involved when I set out to book a trip like this.

  1. The Idea. As mentioned above, it all starts with an idea, which is usually a destination. In this example, it was Paris. My first step was to see if award availability was decent between North America and Paris. It was . On to the next step.
  2. Check Hotel Availability. Before I invest too much time in this, I want to quickly check hotel availability in Paris. Some markets are known to have very expensive hotels (Paris, London, New York etc), while others require a lot of advance notice to book preferred dates. After a quick look, I decided availability was good (though expensive), and I would proceed with flight searches.
  3. Choose a Preferred Airline. After I’ve found basic availability for flights and hotels, it’s time to nail down the routing. I usually decide by choosing which airlines I want to fly. I knew I wanted to fly the transatlantic on United, since i haven’t reviewed one of their most popular business class products – the Boeing 787. Also, I’ve really been wanting to fly Turkish Airlines, so I started the search with that in mind.
  4. Plan Routing/Stopovers. To plan the routing, I considered where I might like to have a stopover, and used my knoweldge of maximum permitted mileage and Aeroplan reward policies to find a destination far enough away to allow for a routing that can take me to my preferred destinations. Usually I choose Singapore (I love Singapore) as the turnaround point, but this time I wanted to try something else. ‘I wonder what the traffic is like in Jakarta at the end of January‘….. Jakarta it is!
  5. Find the availability. I always start with the tough segments first. On this trip, I knew the transatlantic segment would be the most difficult, and was able to find United availability fairly easily coming home. Then I searched for the Transpacific segment, and finally the Jakarta to Paris segment along with any positioning flights.
  6. Book the Flights. Because I was booking a complex reward flight, the Aeroplan online tool was basically useless, as I wasn’t able to get my preferred flights to populate. If you’ve found your segments, don’t drag your feet here. I’ve had award availability change between finding the space and calling in. Thankfully that wasn’t the case this time and the friendly agent processed my ticket, congratulated me on a seriously bizarre routing, and collected my $30 telephone booking fee.
  7. Book any Positioning Flights. On this particular itinerary I wasn’t able to fly from Paris to Vancouver without some really awful flight times. Instead, I decided to open-jaw in Seattle on my way home and buy a separate ticket using Alaska Miles. Always wait until your main award is booked before booking any applicable positioning flights.
  8. Book Hotels. Unless I’m booking fully flexible/refundable hotels, I always wait until after the flights have been booked to secure a room. Hotel availability is much easier to find than flights, and I had taken a quick look at availability before route planning and knew space wouldn’t be an issue.
  9. Research Everything To Death. This is the step where I take to FlyerTalk and research every flight, airline, airplane, hotel, city, etc that I’ll be visiting. This is by far the most stressful and time consuming part of the process. After all, how else will you know exactly what seat is best on a United Boeing 787 in business class or your upgrade chances at the Prince de Galles in Paris?! If you prefer to be surprised, simply ignore this step and sit back and relax and wait for your dream trip!

Booking A Complex Reward Flight – Details Of My Trip To Paris

I’m leaving in a few weeks and wanted to share the flights and hotels I’ll be reviewing, and give some insight into why I selected each airline/property.

The Flights:

Segment 1: Vancouver to Taipei – EVA Air Boeing 777

I’ve flown EVA Air before and consider it one of the best business class products in the sky, and comparable with some other first class products on other airlines. Brad had a chance to fly with them too, and couldn’t find anything to fault. I love EVA Air for their genuine service, comfortable reverse herringbone seat, and first class amenities (such as the coveted Rimowa amenity Kit).

Booking A Complex Flight Reward - EVA Air Business Class

Booking A Complex Reward Flight – EVA Air Business Class

Booking A Complex Reward Flight - Rimowa Amenity Kit

Booking A Complex Reward Flight – Rimowa Amenity Kit

Segment 2: Taipei to Jakarta – EVA Air Airbus A330 Business Class

I flew a relatively short EVA Air business class flight from Singapore to Taipei, but it was operated by the long-haul Boeing 777. This flight will be on the Airbus A330 used for flights within Asia, and will feature a slightly less competitive 2-2-2 configuration with angled-flat seats. I don’t expect it to be groundbreaking, but still leaps ahead of what’s offered on similar distance flights within North America….

Segment 3: Jakarta to Istanbul – Turkish Airlines Boeing 777 Business Class

This is an airline I’ve wanted to fly since I got into travel hacking. All of the reviews I’ve read indicate Turkish offers one of the best overall business class products, with catering by Do & Co (the same company that caters the Lufthansa First Class Terminal), and a lounge in Istanbul that blows the competition out of the water. Interestingly enough, Turkish has a less than ideal 2-3-2 configuration on their 777’s, though I understand the cabin is rarely full and most of the middle seats stay empty.

Segment 4: Istanbul to Paris – Turkish Airlines Airbus A330 Business Class

This is another exciting flight for me, as I get to experience the same business class hard product on the relatively short flight from Istanbul to Paris. Anyone who’s flown business class within Europe knows that it’s usually terrible. Most airlines only offer economy seating with the middle seat blocked off, which is hardly premium. This Airbus A330 will feature the same seat found on the 777, but in a 2-2-2 configuration.

Segment 5: Paris to Washington DC – United Airlines Boeing 787-8 Business Class

While I normally wouldn’t actively look for United Airlines space, this was actually a route I was really interested in flying. I’ve flown the United Airlines Polaris Business Class on the 777 with the new seat, but unfortunately a bunch of the 787’s won’t be getting the new hard product, so I wanted to know just what to expect if flying this configuration. Many of my award booking clients want to go to Europe, and United often has decent availability, so I’m taking one for the team. Although they certainly aren’t groundbreaking anymore, I’ve heard that the business class seats are actually comfortable enough for a medium-haul flight and I’ve noticed service has been slowly getting better on United. Here’s hoping I get a great flight crew!

Segment 6: Washington DC – Seattle – United Airlines Boeing 737-900 Business Class

Not much to say about this flight, except it will probably be terrible. Domestic first class is hardly worth getting excited for, and at almost 6 hours, this isn’t exactly a short flight!

The Hotels

Jakarta – The Ritz-Carlton Pacific Place

I was originally planning to stay in Singapore, but the Marriott properties left me longing for me so I decided to check out nearby Jakarta. Jakarta is actually a pretty cool city, though traffic can be a nightmare. I stayed at recently re-opened Four Seasons Hotel on my last stay and had a fantastic time. Jakarta is great because 5-star hotels can usually be had for about the price of a Holiday Inn in North America. I booked the Ritz-Carlton Pacific Place for 30,000 Marriott Reward points per night, which includes full lounge access. Quite a deal!

Ritz-Carlton Jakarta Pacific Place Standard Room - 786 square feet

Ritz-Carlton Jakarta Pacific Place Standard Room – 786 square feet

Paris – The Prince de Galles, a Luxury Collection Hotel 

The Paris hotel market is really something. Expect to pay well over 1,000 Euro per night for a 5-star property in a good location. Thankfully Starwood and Marriott have a decent selection of properties in the city, though I find most to be overpriced for what they are or in an area that wouldn’t be convenient for tourism. The only one sticking out at me was the Prince de Galles, which was asking a whopping 35,000 SPG points per night for a room that was selling for approximately 700 Euro. Alternatively, I decided to redeem for my first Cash+Points hotel for 15,000 SPG points per night plus a copay of $275. The hotel looks stunning, and is located in one the best areas of Paris, right next door to the famed Four Seasons Hotel (rates were $1,700/night there).

Cash+Points Redemption In Paris

Cash+Points Redemption In Paris

Booking A Complex Reward Flight Bottom Line

As a travel hacker, nothing is more satisfying than booking a complex reward flight and finding luxury hotels around the world for a fraction of the retail price. Though it can be daunting at first, booking reward travel gets easier with practice, and can actually be quite an enjoyable experience. A word of caution though – always make sure you have the proper insurance coverage for your trip. The recent storms on the east coast and thousands of flight cancellations reminded me that no matter how good of a planner I am, sometimes there are factors out of my control. It doesn’t take more than a couple of irregular operations on an itinerary like this to throw everything into chaos.

If you like the idea of stretching your points and miles further, but would prefer someone take care of the steps listed above, consider our affordable Concierge Award Booking Service and have our travel experts do all of the hard work for you! Our Concierge service includes all aspects of reward travel planning, with our experts available 7 days/week to answer any questions related to earning and redeeming points!

Either way you do it, booking a complex flight reward is often more rewarding than a simple itinerary, and can open up more destinations at a fraction of the price!

What’s your experience booking a complex flight reward? What steps do you take when planning your award travel?