One of the downsides of living in a city with a smaller or midsized airport is that it can be tricky to get all of your flights departing out of your home airport at a reasonable cost (in either cash or miles). I live in Cincinnati, which is a decent sized city with a fairly large airport, so sometimes I can book out of CVG with no problems but sometimes I can’t. So what I find myself doing on many trips is booking the “main” part of the trip, and then separately booking a positioning flight from CVG to my international gateway.
For example, on my wife and my first class trip around the world, we got our outbound trip out of Cincinnati, booking CVG-ORD-NRT-HKG-SIN all on one ticket with AA miles (before the devaluation) flying on AA, JAL and Cathay Pacific. On the way back, we used Alaska miles to book SIN-DXB-JFK in Emirates First Class, but because of Alaska’s strange partner booking rules, could not add a JFK-CVG flight on AA on the same award ticket. So we used 4500 British Airways Avios to book that final positioning leg
When my son and I went to Stockholm, we got a cheap cash fare from Newark to Stockholm, and then used United miles to get from Cincinnati to Newark. One important thing to notice is that when you’re on multiple tickets like this, if your connecting flight is late / delayed, you are generally NOT protected against missing your (usually more important) connecting / international flight, like you would be if it were all on one ticket
Forgetting to book positioning flights
However I have found myself occasionally FORGETTING to book the positioning legs on some tickets! Last May, my wife and I booked a trip to Peru in lie flat business class seats.
Again, we needed positioning flights one way.
- IAD-LIM-CUZ using Alaska miles on the outbounc
- CUZ-LIM-IAD/DCA-CLE with AA miles all on one ticket on the return
It actually was not until a week or so ago that I realized that I had never booked our flights from Cleveland to Washington DC! Thankfully miles and points came to the rescue and we used United miles to book CLE-EWR. Even though our CLE-EWR flight was 5 hours delayed, thankfully we had enough buffer time that it didn’t cause us to miss our LAN flight to Lima
Oops! (I did it again)
I was making plans for my other son and my to go to Athens Greece this spring and realized that I had done it again! I had booked a cheap cash fare to Athens out of JFK.
The other day I was looking at some airbnb’s to stay at in Greece (they are so cheap!). If you’ve never used airbnb before, you can get $40 off your first trip of $75 or more by using my link (I get $20)
While I was in the middle of trip planning, I realized that I had no current plan to get from Cincinnati to New York to take my flight to Greece!
Now what?
At least this time, I realized this before the week before our trip! And of course, thanks to miles and points, I have plenty of options
My flight to Greece leaves JFK at 6pm and returns a few days later getting in at 2pm
- I would prefer to fly out of JFK rather than trying to deal with transiting New York airports. As I mentioned above, with connecting flights on different airlines, I am NOT covered if I miss my flight out of JFK
- Similarly I would strongly prefer a nonstop
- AA flies a nonstop that gets into JFK at 2:30pm, and Delta’s nonstop arrives to JFK at 5:59pm. I would feel (mostly?) okay with a 3.5 hour connecting time. It’s too bad that the new Amex Centurion Lounge in JFK won’t be open yet!
- Another option would be to fly in the day before which would give us the whole day in New York to hang out and explore the city.
- On the way back, AA’s flight leaves at 3:30pm (would give me 90 minutes to clear customs) and Delta’s leaves at 6:15pm. I guess I’d think to book AA’s flight, pay with my Citi Prestige card and if I miss it due to connecting, get the Delta flight.
What would you do if you were me?
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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 
Pad your connection time at around 4 hours so CVG-JFK via AA and back through Delta with that buffer inserted so you could do the SkyClub, but you’d be paying extra for your son. That’s what I would do.
Well the connecting AA flight on the outbound gets in to JFK at 2:30 and then our international flight leaves at 6pm so that’s about 3.5 hours. As for the Skyclub, he’s an AU on my Ameriprise Plat (first 3 AUs are free) so he can get in too 🙂
What are your plans in Athens? I am thinking of taking the family there in spring.
I am not sure if there is enough to do there.
Don’t have any plans yet. We’ll be there ~4 days. We may spend the whole time in Athens or we may take a day trip or two somewhere. It won’t be exactly “beach” weather but I’m sure we’ll find things to do. I’ll report back when we’re done
The Athens Natural History Museum is really fabulous ..even for kids and teens and there are loads of other wandering around to do. Fabulous gyros everywhere and easy eating. Not so sure there is four days but we are intentionally traveling slower, getting up later, hanging around sipping wine with college age daughters now so our next visit would be three days/nights.
You might want to look into taking a train to Meteora
Interesting – I’ll add that to my list of possibilities. Looks pretty amazing
Come to NY one day before and 😀