Some people are spontaneous about travel. They wait till the last minute, don't over plan, and let the details evolve organically. That's not me. I am a planner, mostly because I like the sense of calm that the details are worked out well in advance, and partly because I just love planning trips and dreaming about future adventures. In the points world, generally it is more advantageous to plan well in advance, because award flight and hotel availability shrinks as the travel date gets closer.
As I have learned and honed my skills at earning and using points, I have yet the need to look at international flights. But that is changing. Every 5 years my wife and I take an anniversary trip; a trip I usually spend a couple years conjuring, planning, researching, and booking. In 2023, it will be 20 glorious years of marriage for us, so this year I have begun planning it. We decided on a more relaxed paced trip this time, spending half our time in Tuscany and half on the Amalfi Coast in Italy. Now, I know airlines typically open up their schedules 330-365 days in advance, so I did practice award searches all spring, readying myself for when our dates would open up in August 2022. This post will cover how I searched, what I planned to do, and how those plans were completely upended. Plus, how flexible, diversified points helped save the day.
The plan
They say when using points that flexibility is key, because there is often limited availability when looking for free flights using points. If it was a Venn diagram, there would be three main aspects to finding the perfect flight: low miles required (often called saver level), finding the right airports/dates/times, and the flight duration (how many stops/length of layovers). The goal would be to find where they all intersect on the diagram, but it often
requires a compromise in one area, especially when talking about international flights, in order to find a good award flight. In other words, if you want a cheap award ticket, it's doubtful a perfect, one stop itinerary on your exact dates from your home airport will fall in your lap. But with some research and a little luck, getting as close to that ideal is possible.
The parameters for my search were this. I will be starting in Indiana and winding up in Italy. My dates were pretty set based on having our kids watched, but our cities were flexible. I looked at every airport i could reasonably drive to and came up with the following list
From:
Indianapolis (IND)
Chicago (ORD)
St. Louis (STL)
Louisville (SDF)
Cincinnati (CVG)
To:
Rome (FCO)
Florence (FLR)
Naples (NAP)
That allowed me lots of options to look at. Note that I was fine driving to these places, but it would have also been feasible to "position" to another east coast airport in NYC, D.C., Boston, etc. Positioning is buying a separate ticket to get from your home airport to a big hub in order to (usually) find cheaper award ticket availability from the big city. I could have also theoretically looked at flying into big European airports such as Paris, Amsterdam, or Munich and then found a cheap, separate flight to Italy. But for this trip, I didn't want to mess with the hassle and potential complications of 2 separate tickets, so I looked to book a flight the whole way.
Two resources you can use when planning and strategizing award flight are Wikipedia and Flight Connections. If you find the home page for any world airport on Wikipedia and navigate to Airlines and Destinations, it will show you all the non stops from that airport and who flies them. This can give you ideas for which airlines and routes to begin searching.
Flight Connections free version is somewhat limited but achieves a similar outcome in a more visual manner. You can filter by airport to see all non-stops or put in any city pair to see what all your options are between those cities.
The other caveat to my search was that I wanted to fly in business class on the outbound flight. I have never flown up front, would never pay to do it, and thought it would be a great way to start our trip and get some sleep on the overnight flight to Europe. So with all those parameters, I went to work practicing searches on various websites.
Searching
I have miles/points in the following ecosystems:
United Mileage Plus
Chase Ultimate Rewards
Capital One Miles
I heave earned these points through a mix of credit cards sign up bonuses and spend on various credit cards. In anticipation of this trip, I got a United business credit card when the sign up bonus was 150K miles, thinking that booking through United to Europe would be my most logical option. I have mentioned before how valuable Chase Ultimate Rewards are due to their flexibility, and it's a great ecosystem to earn points in for beginners. I got a Capital One Venture card in 2019 when the sign up was 100k miles, not with a specific use in mind but because the SUB was so attractive and also to diversify my points (more on this later). So with those points, I looked at my transfer partner chart to see where I could use these points. As you know with airline alliances, you don't necessarily need points that transfer to a specific airline, because often you can book that airline with a partner. So looking at the chart, with United, Chase, and Capital One, I looked at booking through the following airlines.
This is the tedious part of award travel. Often times you need to set up a free account with various airlines in order to search awards and it takes some time to get a feel for how/where to best navigate the nuances of each airlines' search function. But in general, United is a good stop for searching Star Alliance airlines, British Airways for One World, and Flying Blue or Virgin Atlantic for Skyteam.
On British Airways for my city pairs, I could only find:
This has decent flight times and points, but with all British Airways flights that stop at London Heathrow, the fees and fuel surcharges ($899) are outrageous.
On United, i was looking at several options for my outbound flight. These flights from IND-FCO had great flight times and was the shortest drive I would have to an airport, but were very high in points for business.
This United Non-stop from ORD-FCO was a great flight but a longer drive to Chicago and lots of points required.
Then I stumbled across this flight. Lufthansa is a well known German airline, and they just began a Nonstop from STL-FRA (Frankfurt) this year. I didn't have points with Lufthansa, but as a member of Star Alliance I could book Lufthansa flights with United or Air Canada. I settled on this flight:
The drive to STL wasn't terrible, the flight time with a connection through FRA to Rome wasn't bad, and most importantly, the points were pretty good. In May when I was looking at sample flights, United had it bookable for 77K points plus $42 per person in business class. On Air Canada, another Chase transfer partner, it was only 70K points but $93 in taxes. My plan was, since I already had points parked at United, I would book through them even though it was slightly more points than Air Canada, after all I got a credit card and earned points with United for this very purpose.
That was May, 2022. Now all I had to do was wait for my summer 2023 dates to open up and I would be ready to scoop up this Lufthansa flight, assuming nothing more attractive materialized.
Plan B
What I didn't realize was, looking at sample flights in April and May to Europe is totally different from what may be available during the peak summer travel season. So as my June 2023 outbound date opened up this July, this is what I found (hint, not much). I was hoping that the high point totals I had been seeing may be lower right when the dates became available, allowing me to snatch up the limited supply of saver awards. But all the flights above and others I was looking at still had very high points total for business seats. But, I thought, at least I have my trusty Lufthansa flight STL-FCO:
That's right, not there. Lufthansa, at this point, is not releasing award space for that flight to its partners, so I was out of luck on that one. I could only find United flights for that city pair, and at crazy high points. What I was finding through United was, as of now, there was not really any convenient, cheap points business flights to get me where I wanted to go. I suspect that over the the next year, specifically this winter, that may change and award availability may open up. I could just wait it out, but again, that's not me. I'm not a gambler, so hoping and waiting wasn't a risk I wanted to take, so I kept looking. Back to the transfer chart.
I knew that Emirates, a Dubai based airline, was a transfer partner of both Chase and Capital One and has a non stop flight from JFK- Milan (MXP). I found business class seats at 72.5K points plus $102 as below. Not bad.
But that would require positioning to New York from the Midwest, then taking a train from Milan to Tuscany, not ideal. So I turned to Air France. Flying Blue is the rewards program for Air France and KLM, two huge European airlines but not ones ever on my radar. Chase and Capital One both transfer to Flying Blue, so I searched on Air France. I found this flight that checked most of the boxes.
It had a relatively short travel time, it flew into Florence instead of Rome (closer to Tuscany), and most importantly, it was only 65K points plus $205 per business class ticket, less points (though more $ in fees) than I was seeing through any other program. Plus I read good things about Air France's business class product on the Boeing 787-9. So although it would require a longer drive to Chicago, the positives outweighed that. As they say in sports, the best ability is availability, so I decided to pull the trigger on this flight.
I was prepared to transfer my Chase points to Flying Blue to book the flight, when I paused. As I mentioned, I had Capital One points that have been sitting patiently in my account, waiting to be used. So when I checked my Capital One account, I noticed there was a transfer bonus. From time to time, credit card issuers will offer a bonus to transfer points to specific programs. In this case, during August, Capital One was offering a 20% bonus to Flying Blue. So now, I only needed to transfer 55K points to Flying Blue to get the 65k points per person necessary to purchase the business class ticket. Considering I was seeing ECONOMY seats for that point total with United as well as business seats on other airlines in the hundreds of thousands of points, this was a steal.
Conclusion
Since starting in points, I had never booked an international flight with points, let alone a business class ticket up front. Although looking at international one-ways from a cash perspective is often deceptive, since one-ways are often highly inflated with cash as compared to a round trip flight, I should note that this flight was going for $3246.
Once I subtract the $205 I paid in fees for the award ticket, I got a value of 5.5 cents per point on this redemption ($3041/55000).
What I learned researching this flight was that flexibility and diversification was key. Being able to search and transfer points to multiple airlines as well as having points in multiple currencies allowed my to pivot my plans when the flights I thought and hoped to find just didn't materialize on points, and to strike when a transfer bonus arose.
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