Please ensure Javascript is enabled for purposes of website accessibility

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.

a map of the world with a route

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.

a man and woman standing on a rock with a valley in the background

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.

cc/o from

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?

Points With a Crew has partnered with CardRatings for our coverage of credit card products. Points With a Crew and CardRatings may receive a commission from card issuers. Responses are not provided or commissioned by the bank advertiser. Some or all of the card offers that appear on the website are from advertisers and that compensation may impact on how and where card products appear on the site. Any opinions expressed in this post are my own, and have not been reviewed, approved, or endorsed by my advertising partners and I do not include all card companies, or all available card offers. Terms apply to American Express benefits and offers and other offers and benefits listed on this page. Other links on this page may also pay me a commission - as always, thanks for your support if you use them

User Generated Content Disclosure: Points With a Crew encourages constructive discussions, comments, and questions. Responses are not provided by or commissioned by any bank advertisers. These responses have not been reviewed, approved, or endorsed by the bank advertiser. It is not the responsibility of the bank advertiser to respond to comments.