Warning: this is one of my longest posts ever!
Introduction
Every winter, I need a break from the dreary Chicago weather. So over the winter holidays, we head south. We’ve had a lot of fun over the past few winters!






For winter 2017-2018, we’ve decided to return to Argentina: Mendoza (for six days/five nights) and Buenos Aires (for two days/one night). We like taking 2-week winter vacations, but this year it will be shorter because we’ll be spending Christmas with family in Tennessee.
Getting to Argentina is expensive, so we decided to use our miles and points for this trip even though the winter holiday season is usually a difficult time of year to redeem miles and points. And even though we didn’t have any flexibility with respect to (1) the date we needed to leave the US, (2) the date we needed to go from Mendoza to Buenos Aires, and (3) the date we needed to come back to the US. And even though we’re traveling from a small city in Tennessee rather than our usual airline-hub-city, Chicago.
And did I mention that I wanted to fly in business class in both directions, which is harder to find because fewer business class seats are released than economy seats?
At least I’m only planning for two travelers; if I were planning for a large family, I think I’d be tearing out my hair.
So, how did we do this?
The Journey South
Flights from Tennessee to Mendoza require at least three legs: one to an international hub, one from the US to Santiago or Buenos Aires, and one to Mendoza. (To be fair, that’s true of Chicago too!) I started by going to Wikipedia to find out where I could go from Tennessee. (If you check an airport’s Wikipedia page, the airport’s destinations are listed by carrier. While it’s not 100% accurate, it’s a good place to start figuring out possibilities and it’s one of my favorite travel resources!) I found four cities we could fly to from Tennessee that also have direct flights to South America:
- NYC
- Houston
- Dallas
- Atlanta
We had some flexibility with respect to which airline to use because we had enough Chase Ultimate Reward points (that transfer to United) for two business class saver award tickets one way and enough American Airlines miles for two business class saver award tickets the other way. But we didn’t have any way to put together points for two business class tickets on Delta or its partners, so flying through Atlanta was out!

To get from Santiago or Buenos Aires to Mendoza, we only needed 4500 British Airways Avios points per person to get tickets on LATAM. We weren’t looking for business class seats on that leg (actually, I don’t think there are any!), so I figured that getting this ticket wouldn’t be too difficult.
The most direct routes I found were Tennessee-DFW-SCL-MDZ (on American/LATAM) and Tennessee-IAH-SCL-MDZ (on United/LATAM). There is a LATAM flight from JFK, but that would require transferring between either Newark or Laguardia to JFK. So I really wanted to connect in Texas.
In late December 2016, I started to monitor availability for business class award tickets (well before tickets for my date were to be released) to see if there were any patterns on when airlines released these tickets. Sadly, I found that neither American nor United were releasing their Texas-SCL flight at saver levels for the month of December 2017. Ugh. I really prefer to fly the most direct route possible, but I also knew that I was trying to find saver award tickets to a warm-weather destination during a popular time of year.
Okay, if we couldn’t go in the most direct manner possible, what were the other options? Using AA miles, if we made our way to NYC, there was availability on LATAM’s flights from JFK to SCL. Using UA miles, if we made our way to Toronto (either through Chicago or Newark), there was availability on Air Canada’s YYZ-SCL flight. But I really didn’t want to fly north in late December: that seemed like an invitation for the weather gods to screw us up!
United partners with Copa and Avianca, both of which were more likely to avoid bad weather and regularly released business-class award tickets to Santiago at saver levels using United miles. But Avianca’s options involved more connections, longer layovers and the total travel time would be more than 40 hours from Tennessee to Mendoza!
Which left me with Copa as the most likely possibility: Copa was regularly releasing award tickets for the month of December 2017 and the total travel time between Tennessee and Mendoza was about 30 hours (including an overnight in Santiago, Chile — which means a proper night’s sleep in a proper bed!). The downside: Copa’s business class is a bit like domestic first class in the US: recliner seats (not lay-flat), small planes, few “bells and whistles.” Here’s a pretty accurate review. On the upside, we flew Copa in business class when we went down to South America in 2013-2014 and we really enjoyed the lovely service.
So when I found availability on Copa for my desired date for 55,000 United miles per ticket, I grabbed two seats. We’re flying from Tennessee to Dulles Airport first thing in the morning, then IAD-PTY-SCL, arriving in Santiago around midnight. We’ll spend the night in Santiago, then fly out to Mendoza the next morning. I also found the SCL-MDZ tickets for my desired date without too much difficulty for 4500 BA Avios points.
Total points for two passengers to get to Mendoza: 110,000 United miles and 9000 British Airways Avios.
Schedule-wise, this is the best option for us. Copa has three flights daily from Panama City to Santiago and we’re scheduled to fly on the first one. If there’s a delay, there are two more flights we can take to Santiago and still catch our LATAM flight to Mendoza.
Copa’s business class product isn’t the greatest, but it’s certainly more comfortable than economy and we’ll be flying during the day. I always prefer to sleep in an actual bed whenever possible, so getting to Santiago late at night, crashing in the airport hotel, and then heading off to Mendoza the following morning means I’ll be much better rested for my first day in Mendoza.
From Mendoza to Buenos Aires
This part of the plan is not working and it’s driving me a little crazy. After getting tickets to Mendoza, I thought the hardest part would be getting tickets back to the US. That, it turns out, is not the case! LATAM hasn’t released any award tickets from Mendoza to Buenos Aires on my desired date. I’ll keep searching because these award tickets are a bargain: just another 4500 BA Avios points per person. In contrast, the tickets typically cost about $200 each for a one-way, intra-Argentina journey!

From Buenos Aires to USA
Since we spent most of our Chase Ultimate Reward points on converting them to United miles for the tickets going down, my search for tickets coming home was limited to AA miles. Searching at AA’s website for award tickets to or from South America is not helpful completely useless because it does not include LATAM, it’s major partner in South America, in its search results. (Why? Don’t know. It’s very annoying.) But BA’s site does include LATAM, so I used BA’s site to search for availability.
My options were also limited by the fact that we plan on bringing home multiple cases of wine in our Wine Checks, so I didn’t want to switch planes too often. Unfortunately, there are no direct flights from Buenos Aires to Chicago. The most direct routes on OneWorld airlines seemed to be (in order of my preference based on schedule):
- EZE-DFW-ORD
- EZE-MIA-ORD
- EZE-JFK-ORD
Unfortunately, the first option is only flown by AA, which has been very stingy with its release of business class award tickets. To my knowledge, no business class saver award tickets have been released for the month of December 2017! In monitoring the release of tickets for the month before our desired date, the second option wasn’t readily available either and usually required a long connection in Lima, Peru.
Happily, availability from Buenos Aires to JFK on LATAM was consistently great! Unfortunately, the reason why it was third on my list is that there aren’t many flights between JFK and ORD. But perfect is the enemy of good! So when LATAM released EZE-JFK tickets on my desired date for 57,500 AA miles per ticket, I called AA and grabbed them.
To get home to Chicago from JFK, American has had zilch. But Delta has economy tickets for 5,000 points each. My hotel status with SPG gets us one free checked bag each. My other award ticket option is to keep monitoring AA availability, hope that something turns up, and, if so, book that with Avios points. (If JFK-ORD had been available when I booked the EZE-JFK leg, I could have ticketed the whole trip for 57,500. But if I try to add it now, I’ll incur a change fee. Not worth it!)
If I wait and nothing turns up, I may just need to bite the bullet and buy this leg too. The price for domestic first class ($230) is quite tempting. Even if I do that, I’m still pleased that I managed to nail down the long, trans-continental legs with points, in business class, with a tolerable schedule, over the winter holidays!

Total points spent (so far) to get from Buenos Aires to JFK: 115,000 AA miles. I’ll need to spend another 10,000 SPG/MR, or 9000 Avios points, or cash to get from JFK to ORD.
Accommodations
I seem to have no problems accumulating hotel points, especially IHG points. So I’ve booked us in the Santiago airport hotel, a Holiday Inn, for the first night using 20,000 IHG points (instead of ~$250). Not the best redemption value in the world, but it’s really convenient and we stayed there the last time we were in Santiago on our way to Mendoza, so we know what to expect.
There are options in the city of Mendoza as well as further out into the various wine regions. The last time we were in Mendoza, we rented a fabulous 2-bedroom house within walking distance of the city center. This time, we’ve decided to stay out in the Uco Valley, about 90 minutes south of Mendoza. SPG has a new property there, Auberge du Vin, which was (until March 7, 2017) a Category 3 hotel that cost only 7000 Starwood points per night. Even better, we’ve decided to stay there for five nights, so the fifth night is free! Total cost for us is 28,000 Starwood points (instead of ~$1000). (NOTE: This points bargain is over because on March 7th, the hotel got bumped up to Category 5 and now costs 12,000 points per night.)
There are lots of options in Buenos Aires but I didn’t spend much time thinking about where to stay because we’ll only be there one night. We’re staying in the San Telmo neighborhood at the Anselmo and we’re actually paying for this one! The rate isn’t bad (~$150) while the Hilton points cost is high (50,000) — no brainer! — and we’ll have some time to explore a new-to-us neighborhood in Buenos Aires before leaving.
Conclusion (TL;DR)
Yes, I’m very proud of myself. 🙂 While this booking isn’t the toughest out there (someday I’m going to book us for New Zealand and Australia during the holidays!), it’s not a cake walk either. This is the FIRST time I’ve gotten business class, saver award, international tickets in each direction over the winter holiday season. (I spent a ridiculous number of United miles to get to Mexico in 2013-2014 and a tolerable-but-not-great amount of AA miles to get to Aruba in 2016-2017. The rest we paid for in cash because we didn’t decide on those destinations in time to make award bookings.) I made a few compromises (Copa instead of an airline with lay-flat seats, an extra connection going down there, and we may need to pay for two short legs), but overall, I’m pretty happy.
Yes, I obsessed over getting these seats. Yes, I had a lot of fun doing so. But the time spent actually wasn’t bad: once I figured out the release patterns, I talked to Chris about the kinds of compromises he was willing to make and it was easy to pull the trigger when tickets for our dates got released. Even now, monitoring the Mendoza-Buenos Aires and the JFK-ORD legs isn’t that time consuming. It takes me three clicks on BA’s website (they save my most recent searches) and I check whenever I think of it. If I don’t get these flights on points, it’s not the end of the world.
We’ve spent over 280,000 points and miles on this trip (so far) and I’m happy with the value we’re getting out of these points. Earning hundreds of thousands of points takes time (we don’t often churn through credit card offers for huge bonuses), but points are meant to be spent. We’re rebuilding our points balances and soon we’ll have enough again to think about the next pair of business class tickets that I want for the summer of 2018!