Within the hobby of points and miles, positioning flights are very important. When you are taking advantage of a great international award ticket booking, it may not be to or from your home city. When that happens, you’ll need to book a separate flight to position to where the award ticket leaves from (or arrives to).

This is not the same thing as a connecting flight that is part of the award booking. For example, when we flew to Kenya, my wife, our younger daughter and I all had a flight from Atlanta to Chicago and our older daughter had a flight from Boston to Chicago included in our award tickets booked through American Airlines. That’s an included connecting flight that comes with some protections. Of course, in that instance, had we somehow missed our connection in Chicago, it would have been pretty tough to get all the way to Nairobi, but it would have likely been possible as there is at least one American Airlines partner (British Airways) that could have got us there. We really wanted to take the Qatar Airways flights that we had booked from Chicago to Nairobi via Doha though. One way we were able to insure that we would catch our Qatar Airways flight from Chicago was by including fairly early connecting flights to Chicago and having a long layover at the American Airlines Flagship Lounge. If our early flight had been delayed or canceled, there were other flights to Chicago that American could have placed us on to get there in time for the evening Qatar Airways flight.

When my wife and I met our younger daughter at Newark for our Ireland trip, we took a separate flight on Delta from Atlanta to Newark to position and meet our daughter (who was already in New Jersey) before we all started the Ireland award ticket together. We did something similar in reverse on our return when we landed in Philadelphia. These were true positioning flights. If something had happened with our Atlanta to Newark flight, we ran the risk of missing the transatlantic award flight from Newark. We arrived around 2pm and our flight to London (connecting to Dublin) left around 6pm. Looking back now, I think this was a bit risky. While we obviously could have grabbed a later flight to Newark on Delta or even United, there is a risk in waiting until the day of travel. Delta had no obligation to get us to Newark before our separate British Airways ticket and we could have missed the trip if something happened like the current mess at that airport with lots of daily flight cancellations. On the return, the risk was lower as even if our flight from Dublin to Philadelphia was delayed, we could have grabbed a later flight home to Atlanta or even flown home the next morning. Yes, there may have been an additional cost in cash or miles, but we would not have jeopardized the whole trip.

So, what are some useful tips for positioning flights?

• Worry more about outbound flights than return flights. It’s a good practice to book one way award tickets so you can be flexible if your plans change a bit without messing up the other part of the trip. The outbound positioning flight places a lot more pressure on the overall trip. If you miss your return positioning flight, you can figure something out (possibly even when in the air on the way to the positioning airport). If your outbound positioning flight gets delayed or canceled, it could risk your whole trip.
  
• Book a backup outbound positioning flight. Don’t repeat my potential mistake from the Newark example above. You can use US-based airline programs to make backup plans as award tickets are completely refundable right up until boarding and cash tickets can be canceled for a credit (except basic economy tickets).
  
• Don’t cut it too close either way. My general tolerance for return positioning flights is about two hours. That gives us enough time to get through Global Entry, get bags (if necessary) and go back through security for the domestic flight. For outbound positioning, I like to plan at least four hours, although I usually plan for a bit longer, especially if I have lounge access.
  
• If necessary, book an overnight layover. When we first planned our Southeast Asia trip for 2024, I had booked Washington-Tokyo-Ho Chi Minh City award tickets on ANA. The Washington-Tokyo flight left at 11:30am. There was no way I was going to risk flying up from Atlanta that morning so I booked an evening flight the night before and a reservation at the airport Hyatt Regency. I ended up canceling all of this when we rescheduled the trip and got all the points and miles refunded. Usually, when the outbound award ticket leaves later in the evening, I don’t bother with this, but many people like it as a way to start their vacation early plus it can be a good use of expiring hotel free night certificates from Marriott or Hyatt.

For my YOLO solo trip in July, I have both an American and a Delta flight to Chicago O’Hare booked for my positioning flight to pick up my Emirates GameChanger flight. Not only would I be very upset to miss that flight, it could jeopardize several other award bookings that I have following on soon after that flight. I have an American flight (booked using 9k Alaska miles in first class) at 11am and a Delta flight (booked with Delta SkyMiles) at 1pm. If the American flight is on time, I’ll go ahead and cancel the Delta flight as we’re taxiing out at Atlanta. If there’s bad weather or some sort of mechanical delay with American, I can always cancel that one and take the Delta flight. Either way, I’ll have lounge access on arrival in Chicago to pass the long layover before my Emirates flight that evening (thanks to my British Airways Gold status for American and my American Express Platinum card for Delta). This is how I am self-insuring my expensive award ticket – by having two possible ways to get to Chicago early in the afternoon.

Meanwhile, the day before, my wife is flying to Washington to meet our younger daughter for their group trip to Poland. While I have booked them an award ticket from Washington Dulles late that evening on Lufthansa, she is flying to Washington Reagan early in the afternoon, arriving about eight hours before their flight to Europe. The two of them will then meet up and head to Dulles later in the day. In this instance, I haven’t booked a backup option because there are two airports she can fly into and multiple airlines that can be booked at the last minute if there’s some sort of issue with her current flight. I’ll be available to help her if there’s any issue with her flight. I guess I am her self-insurance in this situation.

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