Why You Should Never Assume SkyMiles Are Worthless: My Recent Success Booking Low Level Awards

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It doesn’t take a lot to convince me to go on a trip – especially when you say the word Madrid and face me with an imminently expiring Hyatt suite award. My best friend Lori lives in Madrid and I usually visit a couple times a year, not only to see her but to revel in the awesomeness that is Spain. I love the food, culture and overall “chillness” that Madrid has to offer – coupled with almost unrivaled nightlife and general affordability (at least in comparison with other European capitals). So recently a couple friends expressed interest in going to Madrid and I had a weekend open in May, so we decided to make a long weekend out of it.

One of my favorite places in Madrid, Retiro Park.
One of my favorite places in Madrid, Retiro Park.

My struggle though is that I’ve been to Madrid more times than I can count and I really like seeing new cities. I also had an expiring free suite night at almost any Hyatt in the world from applying for the Chase Hyatt Visa, so I wanted to max out the value. I love Park Hyatts and have stayed at several in Europe, like Paris and Istanbul, but I had never been to Milan and hear the Park Hyatt there is pretty swanky. So I made a compromise – two nights in Madrid and two in Milan, which met no resistance whatsoever.

Park Executive Suite at the Park Hyatt Milan.
Park Executive Suite at the Park Hyatt Milan.

The next step was booking the flights. I have a lot of Amex Membership Rewards and Chase Ultimate Rewards points, so I figured I’d end up transferring Amex points to British Airways Avios with the current 35% transfer bonus and booking non-stop Iberia flights or maybe even British Airways/Aer Lingus/Air Berlin flights or using Chase Ultimate Rewards points to transfer to United miles for any combination of Star Alliance flights either non-stop from Newark on United or via Germany/Switzerland/Austria/Belgium. You get the picture – there were lots of choices.

Transferring Amex points to Delta didn’t even cross my mind because I assumed no low-level availability would exist for two people on my dates since I wanted to travel with my friend from New York.

For several days I played around with ExpertFlyer and United.com trying to work out availability, but nothing was coming available for our days, except maybe a couple wonky routings like New York-Toronto-Frankfurt-Madrid on the outbound. No thank you. Too much can go wrong and with such a short trip I wanted to make any connections as limited and bearable as possible.

I set a bunch of ExpertFlyer alerts for United and Iberia nonstops, but over the course of a week nothing opened up. Seeing as the trip is less than a month away, I was itching to get something booked which I could later optimize, but even the most basic routings were unavailable on my dates.

For the heck of it, I loaded up Delta.com and to my astonishment there were two low-level awards on my most desired departure date on Delta on a newly configured 767 with lie-flat beds (1/2/1 seating on the seating chart vs 2/2/2. My heart started racing – could this be true? I’ve been burned by Delta.com’s fantasy availability before, so I quickly went through a dummy booking and placed the awards on hold. Holy moly!

For the return, Alitalia had 1 seat available on a Sunday and one on a Monday for Milan to JFK. Monday was the desired date, but I figured I would book myself on Sunday and then set an ExpertFlyer alert and switch for free (since I am Delta Platinum) if the Monday flight ever opened up. In the meantime I’d continue checking the Delta non-stop on the same date, though I really want to try out Alitalia’s new business class on their A330 (I flew their 777 to Miami last year and while the seat was antiquated the service, food and amenities were really nice).

My Business class seat on Alitalias 777 when  I flew it last
My Business class seat on Alitalia’s 777 when I flew it last year to Miami.

I put both awards on hold for 2+ days, which Delta.com allowed me to do since I didn’t have enough miles in my account, and before they came due for actual ticketing Alitalia opened another seat on Monday. Score!

I changed my return to Monday and ticketed both seats. Delta allows you to have a stopover or open jaw, so for each of us I added in flights on Air Europa from Madrid to Milan to get us in between. I booked economy for now since there was nothing available in business class for the times we wanted, but I’m confident something will open up.

I want to try out Alitalia's new Magnifica business class.
I want to try out Alitalia’s new Magnifica business class.

So overall the tickets each cost 100,000 SkyMiles and $74.60 in taxes and fees and I get to experience lie-flat beds on both Delta and Alitalia, and have all flights included for the trip. Just out of curiosity, I looked up what a similar itinerary (minus the Air Europa flight) late in May would go for and it came out to the princely sum of $6,800 (not that I’d ever pay anywhere close to that!) so I feel even better about persevering until I found low-level availability on the flights I wanted.


Oh, and I was able to ask Hyatt to extend the expiration on my suite night, which was supposed to expire at the end of March, and apply it for the Saturday night in Milan, when suites were going for well over $1,000 USD. Overall, I’m happy as a clam and can’t wait for the trip.

So, next time you’re planning travel, don’t discount Delta, even if you’ve had issues with them in the past. And if anyone has any Milan recommendations, I’m all ears!

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