a large white building with a fountain in front of it

Madrid & Istanbul Logistics


As I was writing this yesterday, AA sent out a Travel Waiver notice for the massive Winter Storm about to hit New England. Unfortunately I had already written most of the post below, so I decided to leave it.

Instead of the routing below, after 5 or 6 phone calls to AA (each with a 45 minute wait), I convinced an AA Agent to put us on British Airways and let us have a 23 hour Layover in London, and then continue on to Madrid.

Since there was no Award Availability on BA, the Agent put us on the Flight basically as a Revenue Ticket, so we will be earning Miles going to London! Plus since it isn’t an Award Ticket anymore, we didn’t even have to pay the annoying London Airport Tax!  Not bad for 40,000 AA Miles & $135!


As I talked about yesterday, I had quite the experience dealing with Alitalia after they canceled our Flights.

After finding out about Winter Storm Nemo, I am even happier I am not flying Alitalia.

Via AMEX, I ended up getting my money back and opted to book an Award Ticket to Madrid.

Earlier in the month, I had covered Off Peak Awards on US Airways and American Airlines.

If you haven’t heard about them, I highly suggest taking a quick read because for 35,000 – 40,000 Miles you can get to Europe in the Winter!

US Airways was fully booked for Off Peak Awards, so I looked at American Airlines.

American Airlines

For the itinerary, I had 2 main goals:

  • Get an Off Peak Award for 40,000 Miles
  • Stop in NYC to visit my Cousin who just had a Baby

With that in mind, I began piecing together the Itinerary.

Originally with our Alitalia Flights, we were scheduled to depart on Saturday, so we were going to fly via Southwest to NYC on Friday Night so I could visit my Cousin.

Well when we switched our ticket to American, you are allowed to have a 23 hour Layover free of charge.

So in my case, as part of the Award, I booked an AA flight from Chicago for Friday Evening after work, planned to stay in New York Friday Night, see my Cousin Saturday Afternoon, and then fly onward to Madrid out of JFK Saturday Evening.

With this new routing, I saved my Southwest Points, and got 23 Hours free in NYC!

For the flight to Madrid, we were able to book a direct flight from JFK on AA.

Coming back from Madrid, availability was really bad. The reason for this is that One World doesn’t have as many Hubs in Europe as Star Alliance does. To make matters worse, if you connect your Flight via London, you get hit with a hefty Departure Tax, even if you don’t leave the Airport.

So while I wanted a Direct Flight back to Chicago, I didn’t want to go thru London because the Taxes would be around $250 each (or close to the price we were going to pay for the round-trip Alitalia ticket).

I set an alert on Expert Flyer and began checking everyday for anything to open up on AA.

Last week, finally a MAD – JFK AA Flight opened up, so I jumped on it and put a hold on it while I called Alitalia and eventually AMEX.

After AMEX returned my money, I went ahead and booked the Chicago -> New York -> Madrid -> New York Flights.

Obviously I don’t live in New York, so it may seem kind of stupid to stop in New York but there is a method to the madness.

There were no New York -> Chicago AA Flights available on President’s Day when we come back, so the option was to stay over night and get a Flight the Morning. That didn’t really sound appealing!

So instead, what I did was book a Southwest Flight from LaGuardia to Chicago, that will get us home on the 18th. We will just land in JFK and then take a cab to LGA, which isn’t a huge deal.

Similar to United, AA allows you a Free Stop Over, however it is limited to your Gateway City (ie. the City you first fly into), which in our case it was New York. MileValue covered it in detail here.

Since I have family in Manhattan, I knew I would be back again sometime this year, so instead of ending the Flight in NYC, I simply added in a 7 month Stop Over in NYC and then tagged on a Flight back to Chicago sometime in September (I can change the date for free since it is so far out).

Whenever I decide to go to NYC, I can just book a One Way on Southwest to get there, and then I will have a free AA flight back!

All in all, the Itinerary looks like this:

February 8

Chicago -> New York (LGA) on AA

February 9

New York (JFK) -> Madrid on AA

February 18

Madrid -> New York (JFK) on AA

New York (LGA) -> Chicago (MDW) on Southwest

Sometime In September

Chicago (MDW) -> New York (LGA) on Southwest

New York (EWR) -> Chicago (ORD) on AA

In total, for 2 tickets to Madrid it cost me 80,000 AA Miles + $271.60.

The Southwest Flights will cost around 14,000 Pints.

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As you can undoubtedly see, $150 or about 45% of the $271.60 is just non-sense Close-In Ticketing Fees.

Without that $150, we would have paid around $60 each in Taxes.

Although it sucks having to pay more for the Close-In Ticketing Fees than the actual Taxes, in this instance I am more than happy to pay it to avoid having to fly Alitalia.

Overall, with the AA Off Peak Awards, we got a pretty phenomenal deal because a Revenue Ticket to Madrid including the 23 Hour Stop Over, would be around $1,300 and doesn’t even include the Free One Way back to Chicago in September!

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Istanbul Flights

Normally with all Flights I take, I always check Kayak.com first to see what the average price of a Ticket is.

If the cost is close OR less than 1 Cent per a mile, then I opt to just pay for the Ticket out of pocket. Thankfully that normally doesn’t happen too often!

For Istanbul I did a quick search and pulled up the following:

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Normally, with a Flight that costs $300 it makes more sense to redeem 25,000 Miles for an Award, rather than pay out of pocket. (This is just personal preference, others may disagree)

However in the EU, there are tons of low cost Carriers like EasyJet, Ryan Air, etc., so I figured it was worth a shot to see if we could fly those. Unfortunately Turkey is not served by those Carriers : (

I talked to my Friend Chris and he recommend SkyScanner.net for cheap European Flights.

Lo and behold, an almost identical Flight on SkyScanner was only $239, instead of $300 on Kayak!

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Although it was nice to save $60, it also complicated the decision whether to use 25,000 Miles for an Award Ticket or pay $238 out of pocket. 

When you are trying to buy Miles, you want to shoot for under 1 Cent Per a Mile, but when redeeming Miles, you want to go as high over 1 Cent per a Mile as you can.

In this case, the CPM for redeeming an Award Ticket was $0.009, which is terrible!

So in the end, as much as I HATE paying $238 out of pocket for Airfare, I know that those exact same 25,000 United Miles are worth substantially more than $238.

So in the future, I could for example use those same 25,000 United Miles for a Domestic Flight to San Francisco which costs $488!

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As convoluted as this sounds, by spending $238 now and saving my 25,000 Miles, I will actually be saving money over the long run because I will put those Miles towards more expensive tickets.


New York

Last Fall when Club Carlson had their Stay 1 Night, Get 1 Night promotion, I made the case that it was a phenomenal deal because you could essentially use those Free Nights at properties that were $400 a night.

I went ahead and did 2 different Paid Stays at Radisson LAX when I was out in LA. These were real stays and not just mattress runs. I paid around $80 for each stay, which got me a Night at the Hotel (which I needed anyways) + a Free Night Certificate.

When I realized that we needed a Hotel in New York for our 23 Hour Layover, I burned one of the Radisson Free Night Certificates.

So instead of paying $283 for a Hotel Room in New York, I paid $80 back in November, got 1 night in LA and now and now am getting a FREE NIGHT in NYC!

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When I went to Madrid in 2010, my Friend Chris and I ended up staying in Hostels for about $40 each a night.

This time around, I am going with 2 Women and there will be 3 of us, so I figure it is about the same price to split a Hotel Room.

When I started searching for Hotels, I did the normal SPG.com, Hyatt.com, etc, search for Awards.

Unfortunately I didn’t see anything too appealing.

I did remember that Radisson has quite a few Radisson Blu properties, so I checked those out too but didn’t find anything especially worthwhile.

I headed back over to Kayak and started looking at Hotels but since everything is in Euros, everything was a bit pricey.

I wasn’t really sure what the Hotel game plan was going to be until Gary posted a phenomenal Hotel Deal 2 weeks ago.

Basically if you were a USAA Member, you could log in and book Hotels via their Hotel Partner for 40% OFF ANY HOTEL!

Thankfully I was already a USAA Member as I had used them for Under Age Car Rentals, not to mention that it is free to join, so I hopped right on the deal.

I saw the deal after it had been posted on Gary’s site for 24 Hours, so the prices had already gone up a bit and they had added some minimum spend restrictions, but we still got a great deal.

For Madrid, we booked the Westin Palace Madrid, which as you can see below is simply stunning!

a large white building with a fountain in front of it

a large glass dome with a chandelier and a couch

The price on Kayak was $274 a night, not including Tax.

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Via USAA, we paid $653.40 for 3 Nights including Tax. 

That comes out to $218 a night, or a savings of 28% once you factor in the Tax.

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For Istanbul, I still have Hyatt Diamond Status until the end of February from SMD4, so we were going to either do the Park Hyatt Istanbul or Grand Hyatt Istanbul, but they were both quite pricy.

Unfortunately those 2 properties were not part of the USAA sale but the W Istanbul was!

Kayak had the W Istanbul at $256 a night for 4 nights, via USAA we ended up getting it for $158 a night or a 39% discount.

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The only thing that kind of stinks is that we were planning on using my Friend’s SPG Platinum Status (by tagging him on as a “guest whose flight was delayed”), so we could get a Free Suite Upgrade, Free Breakfast, Free Internet, etc, BUT apparently Elite Benefits do not apply to 3rd Party Reservations, which is really stupid!

Can you imagine if Airlines did that? Sorry you booked your United Ticket on Expedia, so even though you are a 1K, you won’t earn any Miles or get any Elite Benefits on this Flight…

I did some research online on how to circumvent the 3rd Party Booking Policy. I am not sure if it is going to work, but we will see…


Although it was a major hassle dealing with Alitalia, with this Winter Storm Nemo approaching, I am EXTREMELY GLAD I got out of those tickets!

With AA Off Peak Awards, I really think we got a steal especially now that we got booked on British Airways and will earn Miles on that Flight, plus get to spend 23 hours in London!

Although this trip isn’t going to be as cheap as I would have hoped since we are paying out of pocket for Hotels and Istanbul Flight, that USAA discount really saved us since got some fairly reasonable prices at some really nice Hotels.

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  1. In regards to the Westin, $218 per night is awesome… however, if Cash and Points were available, would that have been a better value? Thanks

  2. Turkey actually is served by a bunch of low cost carriers including TK's own Anadolu Jet, Pegasus Airlines, AtlasJet. Some of them use Sabina Gocken instead of IST-Ataturk for their Istanbul flights though.

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