Flight Booking Strategies
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Use point.me for powerful award ticket searches
Search gateway cities and look for mixed-cabin awards
Use Google Flights and search "multi-city" when booking paid flights to Europe
We'll admit it... We're spoiled when it comes to flying. We haven't done a flight over 6 hours in economy class in a very long time. So, how do we do it without breaking the bank? Before you read this article, make sure to check out our info about the best credit cards to earn points and miles. Once you've done that, read on!
Use point.me for award travel searches
Our favorite tool for doing award ticket searches is point.me. The launch of point.me's search engine came at a fortuitous time for us, as we were just about to start our epic adventure. Point.me returns results for most of the major airline reward programs all in one place rather than you having to go search each airline program one-by-one. This is really helpful if you're using our strategy of accumulating transferable points. We'd otherwise have to run upwards of 20 different airline website searches to get the same results. As of right now, you can only search one day at a time, so we find it helpful to do our point.me searching on our laptops so that we can have multiple browser tabs open and searching for a few days around the time we know we want to travel. So far, we found our business class flight from Miami to Santiago, our business class flight from Europe to South Africa, and our business class flight from Guayaquil to Lisbon all by using point.me. It's well worth the annual fee for us. They currently have a starter pass for $5 where you can search for 24 hours and test out their capabilities.
Point.me also offers a concierge service. For $200 per passenger, they will do all the searching legwork for you and present you with options to use your points and miles. This can be great if you're not a big do-it-yourself-er or if you have a complex itinerary (extra fees may apply with complex bookings). Stephen's parents used the concierge service for their big three month trip to Asia and Australia. We told a friend who had posted on Facebook about his frustrations trying to use his miles to go to Spain about point.me. He decided to use the concierge service, he was super happy with what they were able to find for him, and we had the satisfaction of seeing all his pictures posted on Facebook during his trip. When paid business class travel is upwards of $10,000 for long flights (especially to Asia), a $200 fee for having a professional figure out how to use your miles is well worth it!
Search gateway cities to find better award availability
This is becoming less useful with some airlines that are now using "married segment" award inventory where a flight from Miami to Madrid through NYC is available, but not just the flight from NYC to Madrid (We're looking at you American Airlines). Often it's the "local" segment (typically in the US) that is not available for booking. For example, when we needed to get from Jordan to Minneapolis to share Thanksgiving with Stephen's extended family, we knew that Royal Jordanian is a partner of American Airlines where we have a lot of miles built up from when Eli was traveling for work. We couldn't book the flight all the way from Amman to Minneapolis using American miles without a crazy routing with 3 stops, but we searched all of the North American destinations that Royal Jordanian flies to. We found the best combination of those flights available for an award ticket with a separate purchase of a short flight with cash to get us to Minneapolis when we wanted to be there. The total cost was 70,000 miles each plus $357 for the connecting flight... not a bad deal for 11 hours in business class (plus about 2.5 hours in coach and a 4 hour layover... which turned into a little longer due to weather).
Also, it's worth seeing if the short connecting flight segment is available as an award in economy vs. business class. Some airlines will show this for you (and point.me shows you this option when available), but we've called up customer support and had them look for us. We did this with our flight from Guayaquil to Lisbon when Iberia changed the time of our connecting flight from Madrid to Lisbon to even later than it was originally. There was an earlier connecting flight without business class availability, but there was economy availability for an award. The helpful agent at American (whose miles we were using) was able to book the better connecting flight in economy and have it covered as part of our original award cost.
It can also be helpful to do gateway searching on point.me as well, but get your feet wet with some regular searching using their site first before digging in to power searching.
Book roundtrip flights to Europe if you're paying in cash
This is really not true anymore for flying domestically in the US, but for flights to Europe (and sometimes Asia), it is almost the same price to fly one-way from the US as it is to fly round-trip if you're paying cash. This includes "open jaw" tickets when you fly into one city on the continent and fly out of another. The best way to search for paid flight tickets is by using Google Flights. If you want to search "open jaw" tickets, select the multiple city function on your Google Flights search.
Also, if you know you're traveling frequently back and forth, round trip business class is often cheaper Europe to the US than US to Europe (no idea why, but it is).
If you run into payment problems, book through an Online Travel Agency (OTA)
While we're going to be in Africa, we're flying some lesser-frequented airlines. Kenya Airways has a US website, and you can book tickets through it (at least theoretically). However, we couldn't get any of our credit cards to work to actually purchase the ticket (and we tried them ALL). Instead, we booked through the online travel agency associated with our Capital One Venture X card (so we got the $300 travel credit) and we got tons of extra miles for the purchase.
We wouldn't typically recommend that you use an OTA if flying just within the US as it can be a hassle in case of a cancelled or rescheduled flights, or when there are irregular operations due to weather.