One of the risks that many frequent travelers take is that of combining multiple flights for a single trip. I feel like this is more of a thing for people using miles and points, just due to the flexibility that miles and points give you in being able to position yourself to a different place than your home airport. These flights are often called “positioning flights”, and the risk you run is that if something goes wrong with your positioning flight, it can cause very bad consequences to the rest of your trip.
(SEE ALSO: Connecting flights on different airlines: When it’s a bad idea)
I’ve ran into this several times, including on my first ever business class flight, which was on Aer Lingus from Boston to Dublin (RIP Avios Boston sweet spot), which ended up being completely cancelled. While this wasn’t a true positioning flight, it did mean that we missed out on the one day we had scheduled in Dublin.
A European Adventure
I recently returned from a trip with my dad and sister to Europe. As the “miles and points guy”, I was responsible for all of the flights on the trip, and I had booked the 3 of us using Alaska miles in American Airlines business class from Dallas (DFW) to Frankfurt Germany (FRA). I figured this would also give us a chance to check out the amazing Capital One Lounge in Dallas. Because we all live in different cities, I had to book the tickets separately.
From Houston, it was no problem to get to Dallas, as there were tons of American flights available, even though at first I ended up getting an Alaska partner error saying “we’re sorry, we’re not able to confirm space on these partner flights”.
My sister lives in Sacramento, and I was having trouble getting anything workable from anywhere in California to connect to this DFW-FRA flight, even though there were tickets available on the long-haul flight. Eventually, and with only days before the trip, I decided to just book her on a flight from Sacramento to Cincinnati, and she could stay with me and we would fly to Dallas together.
Booking A Positioning Flight
I used United miles to book her flight, and I decided not only to book it for the day before, but to book it for TWO days before.
- Our flight from Cincinnati to Dallas to Frankfurt was on October 4th.
- I booked her flight from Sacramento to Cincinnati for October 2nd. The flight went through Chicago and left at 2pm, arriving in Cincinnati around 11:30p.m.
My thinking was that this would give us a bit of extra time in case something went wrong, and we wouldn’t have to worry about things going sideways in case there were problems with her flight. Plus, that would give her a bit of time before having to fly again, and everyone was excited to see their sister / aunt / sister-in-law.
Flight From Sacramento Cancelled
I didn’t really think that there would be trouble, but I wanted to hedge against devastating downstream consequences. And as it turned out, it was a good thing that I did!
I had been tracking her inbound flight, which arrived to Sacramento okay, but then there was a maintenance issue. She only had about a 50 minute connection in Chicago, and as the delay increased, it became more and more likely that she would miss her connection. Sure enough, it ended up being that they canceled the flight entirely.
She had a few options, but ended up deciding to take a redeye to Newark and then onto Cincinnati the next morning, arriving to CVG around 11 a.m. That was fine since I had booked her an entire extra day of buffer time, but it would have been pretty bad had I not, since we would have missed our 8 a.m. flight from Cincinnati to Dallas. And since these flights were on different airlines, I’m not sure if United would have flown her to Dallas instead of Cincinnati? I probably would have been on the hook to get her there myself, and even though I had paid for her ticket with the Capital One Venture X card, I don’t think the Venture X trip delay insurance would have applied, since she’s my sister and not an immediate family member.
So I was glad to not have to worry about that!
The Bottom Line
Booking positioning flights can be an important strategy in maximizing the value of your miles and points, but it is not without risk. Whenever I am booking positioning flights, especially on different airlines, I always try to give myself as much time as possible. That way, if (WHEN) things go wrong, you have enough time to get things fixed without it causing disastrous issues with the rest of your trip.
Have you ever been bitten by a canceled or delayed positioning flight? Leave your thoughts in the comments below
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
I often build in overnight stops for positioning flights, particularly when it’s just me. My wife hates having an overnight in D.C. then another in Doha, then another in Bangkok on the way to Cambodia for example and it’s tough to blame her. Unfortunately the alternative is often spending 6-8 hours in a lounge, which makes even a nicer lounge seem tiresome.
One thing I always try to avoid domestically is taking the last flight of the day to my destination unless I’m willing to not arrive until the following morning.
Yeah – that’s a great point. Taking an earlier flight in the day definitely feels like it increases your chances of making it there the same day
I do the same thing out of paranoia that there will be trouble on the positioning flight… I’d rather spend a night at a hotel than have to deal with a cancelled/delayed flight on a separate ticket as my positioning is usually with Delta or Jetblue and the longhaul is with ANA.
When I flew out of Boston for Tokyo on JAL, I would Uber the night before and stay in the airport Hilton since I’ve missed other flights trying to get to Logan from the suburbs due to traffic/construction, etc. during the daytime.
Flying out of JFK, I’d go the night before for a 10AM the next morning.
Same with ORD, but it’s not ideal since the flight is at 5:45PM and I have to check out of the hotel by 11AM.
The Hilton ORD at the airport offers day rates, which might help. Sometimes my wife and I will take a very early flight in then stay at the Hilton for a solid four hour nap. It’s nice not to have to rely on shuttles to get back to the terminal.
Reminds me of the nightmare scenario I had a few years back.
Flying UA from STL to IAH on one ticket and then SG to Europe, same day flight with a 4 hour layover. What could go wrong?
UA flight from STL to IAH was delayed, delayed, delayed and then the crew timed out. Flight was cancelled and no other way to get to IAH on time.
I ended up getting a UA flight the next day to ORD and then on to Europe. Lost a day of the trip but at least the LH flight was in F on a 747. That part was great but the rest was pretty stressful.
I’m going to the Maldives next April and leaving out of DFW. Needless to say, we are flying in the day before.
You’ve nailed it! Positioning flights do come with added risk, especially for travelers using miles and points. It’s a great reminder to plan carefully, as delays or issues with one leg can have a ripple effect on the rest of the trip. Very insightful for frequent travelers!