The Basics

Award Booking Anxiety – Which Flight Now?!

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Written by Charlie

Award booking for flights can be both fun and also cause anxiety at times when you are stuck and not able to book that perfect flight! But, in the end, I got everything I wanted for a little cash and miles!


If you have been in the award booking game for a little while, you know that if you have great flexibility, you will normally have better access to the awards you actually want. Furthermore, it can also help if you wait until closer to departure as well for that perfect award to open up. But, it can sometimes create some award booking anxiety in the process!

Award Booking Anxiety

I have to be in NY very soon and I had kinda booked my award ticket a couple of weeks ago. Fast forward a bit and I began rethinking some of the awards I had already plus something new hit my schedule and since I will only be in NYC for about 30 hours, I to make the schedule tight to fit everything in.

– Quick note: I actually had originally planned to book paid business class on Turkish Airlines from Greece to JFK since Turkish never penalizes you with a minimum stay requirement (especially like a Saturday night stay like the US airlines require for the cost to stay low).

Plus, I could book using Membership Reward points out of my Business Platinum account and get a 50% rebate since it was a business class ticket. When credited to Aegean, it would add up to quite a haul towards my next business class award – 1/3 of the required miles, as a matter of fact.

But, the electronics ban eliminated Turkish as an option since I am traveling with more electronics than I care to check so I had to go looking elsewhere – enter the “award booking anxiety.”

Initial Awards

Europe to the US

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Lufthansa Business Class | This was my first seat booked – but not what I will be flying!

For my outbound, I booked business class (there wasn’t even economy available!) using Aegean miles – total was 45,000 miles for the one way business class ticket. So, outbound done – right? 🙂

US to Europe

No business class open on the return on the Turkish Airlines flight I needed so I booked economy on Turkish Airlines from JFK with United Airline miles – 30,000 miles. I really wanted to find business for the return, since I would hit the ground running, but at least I had my return!

US flights

Next, I had to take care of my flights from NYC to upstate NY. Amex Business Platinum 50% rebate to the rescue! I booked business class on Delta for just $20 more than coach and that gave me elite access (I am no longer a Delta elite) and was able to get 50% rebate on the points I used. Total price for 2 one ways in points? Only 13,000 Membership Reward points for a roundtrip first class ticket on a regional Delta jet. The access and baggage were more of importance to me than the seat but I will take that too!

Award Booking Anxiety Sets In

Europe to the US – Round 2

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My new flight – Lufthansa First Class! | Photo from Lufthansa

Ok, I should have been happy with it but then I got my 250,000 mile windfall! I decided to change my Aegean award from business to first class on Lufthansa since I haven’t flown Lufthansa first class in 4 years and also have not flown the “new” first class. Also, it would only be a $22 change fee and no increase in the taxes/fees plus an additional 15,000 Aegean miles. Win! Lufthansa first class booked for 60,000 miles!

US to Europe – Round 2

I ended up finding an award that would take me from western NY to Chicago and that would put me on Turkish business all the way through. I decided to use Aeroplan miles for this since there were no fuel surcharges and Aegean does not let you have more than 1 connection. Also, Aeroplan only requires 57,500 miles for that itinerary while United would require 70,000 miles (and a close-in booking fee of $75). I booked that so I had my business class ticket back to Europe!

US Flights – Round 2

But, now I was departing from Rochester with a different flight and would no longer need my Delta tickets. I started watching some tickets and also planned on doing a SDC (same day confirmed) with Delta for $75 to move my Delta ticket to an earlier flight. That is, unless I could get a ticket for cheaper than that! I stuck a pin in the US flights and started to settle in with my new itineraries.

Award Booking Anxiety Goes Up

US to Europe – Round 2

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This is what I am flying back to Europe – Turkish Airlines Business class

This morning, Turkish finally released business class tickets on the original flight I needed! Yes! Now, while I have booked Aeroplan tickets before, I never had actually cancelled/changed one before. I thought it would be like with other sites that I could go ahead and do it online. From what I saw, it seemed I could cancel and then rebook. But, it turns out you need to rebook with an agent. The problem? The Aeroplan call center did not open for another 5 hours!!!

And, guess what? I had just cancelled my Aeroplan award so now I did not even have that flight left! This is where my award booking anxiety took off! I needed that final Turkish Airlines leg for my return and I could not rebook until Aeroplan opened.

What to do? I could book it with United but really did not want to pay 70,000 miles for this. I could also book with Aegean for 45,000 miles but I had this cancelled Aeroplan award that I would need to use within a year and I didn’t want to deal with that. So, I waited, and waited, and waited.


Finally, Aeroplan opened and I was able to grab the seat I needed. Now I was finally done! I tell you, it feels good but I also know that award booking anxiety is real and it actually can help make the final resolution a little sweeter when it is done. 🙂 Thankfully, I have every flight I wanted and am glad I get to fly Lufthansa first to the US and Turkish business back (since it gives extra time for sleep being a 10+ hour flight).

Do you ever get award booking anxiety when flights start to disappear or you get stuck with miles not posting fast enough? 🙂

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About the author


Charlie has been an avid traveler and runner for many years. He has run in marathons around the world for less than it would cost to travel to the next town - all as a result of collecting and using miles and points. Over the years, he has flown hundreds of thousands of miles and collected millions of miles and points.
Now he uses this experience and knowledge to help others through Running with Miles.


  • I had high anxiety on an Aeroplan award in Sep 2014 when I left for my first int’l award trip in First (TUL-ORD-EWR-BRU-MAD). Minutes before boarding the first leg that tower fire at ORD happened. Flight cancelled to ORD. I didn’t call Aeroplan to cancel my ORD-EWR portion. Got to EWR via DFW but they couldn’t find me in the system anymore. Aeroplan couldn’t help. UA gave me my seat (whew) and in BRU same problems. Put me in coach on UX (Air Europa). Ugh. But was glad to get to MAD. Then, no luggage until 4 days later. Call Aeroplan immediately if first leg (or any) is cancelled.

  • Couple of years ago I was planning our anniversary trip. Able to booked one ticket on CX in F, 10 months out. For the next 9 months and two weeks, my daily anxiety built as I monitored BA site for another seat to open. Can’t tell you how relieved and excited I was when it finally said Available. (Best seat/bed in the sky, BTW – better than SQ suite and even JL F.)