The other day, a coworker of mine mentioned that he wanted to fly to New York next month. Since I am well known around the office as the miles and points guy, he stopped over to chat about it. He said that he had about 22,000 American miles, since he had signed up for a US Airways card a few months ago with the 50,000 bonus on the first spend (and those since had been converted over to American AAdvantage miles)
(SEE ALSO: What I’m doing now that American and US Airways miles have combined!)
Step 1: Look at availability
He didn’t have any specific times that he was looking for, so I pulled up aa.com, and looked at CVG-JFK routes
The good news is that there is tons of low-level availability throughout November and December, and most of those dates even have availability on American’s once-daily nonstop flight from CVG-JFK.
Step 2: But wait… there’s more!
You’ll remember that I said that he only has about 22,000 American miles, and a roundtrip award flight on American costs 25,000 miles, so he didn’t really have enough miles to book the flight. But then I remembered that Cincinnati is on the list of airports for American’s Reduced Mileage Awards for the next 4 months!
(SEE ALSO: The 62 airports where you can fly anywhere in the US for under 8,000 miles)
Because he has the American Aviator Red card, he is eligible for a 7,500 mile discount on a roundtrip award. Reduced Mileage Awards can’t be booked online, so I told him he’d need to call.
I also told him to make sure that the award cost 17,500 miles and $11.20 and that if they tried to charge anything more than that, to hang up and come get me. I’ve learned that with people who aren’t used to miles and points, that it really is a good idea to spell that out, since oftentimes, especially with phone agents, they like to come up with random fees to charge.
In this case, it turned out that was a good idea – he came back a bit later and told me they tried to charge the 17,500 miles plus $86.20. I had forgotten about the $75 close-in booking fee!
While there are a few ways to get around paying the $75 close-in booking fee, in this case it would require he have Alaska miles or British Airways miles, which he doesn’t have, so I suggested that since he was flexible on his dates, he just pick dates that were further than 21 days out
Step 3: It could have been even cheaper!
15,750 American miles (he’ll get a 10% rebate on his 17,500 miles due to having the Aviator card) is a pretty good deal, but it actually could have been cheaper. Since CVG-JFK is fewer than 650 flown miles, this would be a perfect time to use British Airways Avios.
It would be 4500 Avios one-way from Cincinnati to New York (or Chicago, Philadelphia or Washington DC), or 9000 Avios roundtrip. He actually already has some Chase Ultimate Rewards from a Freedom card, but would need a premium card like the Chase Sapphire or Chase Ink to be able to transfer them to British Airways. We talked through doing that and he said he was definitely interested, but wanted to go ahead and book the ticket with American miles now, rather than wait for a Sapphire.
The bonus from the Sapphire would be enough for close to TEN one-way flights, and is definitely a card worth getting for someone with his travel patterns.
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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 
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