My rookie mistake: not linking flight reservations

My number one piece of advice for booking airfare is to always search for only one ticket, even if you need three or four seats.

Airlines have odd pricing systems. Let's say there are two seats left at $99 and then the next cheapest ticket is $120. If you search for four seats, all four will price at the higher $120 cost.

This is all about how many tickets are left in a fare class or "bucket."

So a trick to save some money is to buy two tickets at $99 on one reservation and the other two at the $120 price on another reservation.

That usually works unless there is a massive schedule change, storm, mechanical problem or some other delay.

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Back in March, I booked a trip on Delta Air Lines from New York (JFK) to Cancun (CUN) for my family for the 2021 February school break. Airlines typically open up flight schedules 330 days in advance and I wanted to get a good mileage flight before others booked during the popular travel week.

(We will see if we actually take the trip based on how the fight against coronavirus goes. But as a Diamond Medallion elite member, I can redeposit my miles for free up to 72 hours in advance — the perfect pandemic insurance policy. The hotel was also booked on points with a flexible cancellation policy.)

For the flight down, I found three tickets together at the same mileage cost. But for the return, it was cheaper to book two reservations. I booked one ticket for my wife at 27,000 miles one way in first class. My daughter and I each paid 47,000 miles for our one-way first class tickets. (Not the best use of miles but the flexibility here is key for me.)

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Normally, I would then call Delta and link the two reservations. That way, if there are any changes, the airline will hopefully try to keep my family together.

Well, blame it on my exhausted, pandemic mind but I failed to do that. There were also some pretty bad wait times at Delta's call center back in March.

Fast forward to September and I got the schedule change email. At first, it didn't look bad. My daughter and my mid-afternoon flight was shifted 20 minutes. Then I looked at my wife's ticket. She was moved to the morning flight.

Oh no.

I called the airline and sure enough the flight was sold out in first class. So was Comfort+.

Delta was able to downgrade my wife to coach. The agent was about to give me back the difference from her 27,000-mile first class ticket and the new mileage price for coach. Then she priced it out: 74,000 miles, one way for coach. So no difference in miles but she was given a $200 travel voucher for a future trip and is still able to move up to first, if a seat opens up for sale.

Bottom line

The splitting up of my family could have been easily avoided. I tried to save money by booking two separate tickets. That was the right call. But then I should have immediately called up Delta to link the reservations together. That would have kept us all together when the schedule change occurred. It's something that I've done countless times but failed to this one trip and it hurt me.