- Tommy Obenchain
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- How I Find Flights (Cash or Points) in 2025
How I Find Flights (Cash or Points) in 2025
A quick look at two tools that save me time, money, and miles—every single trip👇🏼

Friends,
I love planning trips. Not just going on them, but actually sitting down to figure out the best flights, connections, and redemption strategies.
And this is not something new. When I was in second grade I learned you could call airlines to find out the price of fares. In one way or another I have been doing it ever since.
To me, it is like solving a puzzle — and two tools I use constantly are Google Flights and Seats.aero.
Let me break down why both are worth knowing (and using).
Google Flights: This is my go-to when I’m paying with cash or just exploring options. It’s fast, flexible, and lets you do more than just plug in two cities and dates.
Multi-city/destination tool? A serious dream. Want to go from Dallas to Paris, hop over to Vienna, then fly home? Or see the cheapest fares from one continent to another on a given date? No problem — plug it all into one search.
Flexible calendar? It shows the cheapest days to fly across an entire month, which makes it easy to time your trip around the best fare.
Price tracking? You can turn on alerts and get emailed when fares go up or down. I use this one the least, but it sure is neat.
And my favorite: the “Explore” feature. Enter your departure city, and it’ll show you where in the world you can go for cheap. It’s fantastic for everything from finding crazy cheap economy fares to discounted business and first class seats.
Seats.aero: This one’s for award travel. If you use points or miles — even occasionally — it’s a must-have.
It pulls live award availability from dozens of programs (like American AAdvantage, United MileagePlus, and Aeroplan) and shows you which dates still have seats. No more searching site by site — it’s all right there. It’s not always 100% up to the minute, but it’s incredibly efficient for spotting patterns and award space.
Best part? It’s fast and free to use, though they do have a paid tier for more advanced searches. I have only needed the free feature thus far.
Big Picture: I use Google Flights to figure out if I should pay cash. I use Seats.aero to find out if there’s a good points deal. Between the two, I rarely miss out on the best options — even on complicated trips.
If you’re not already using them, I highly recommend giving both a try next time you plan something.
And as always — if you need help figuring out your next great itinerary, I’m just a reply away.
Fly well.
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Links
First new cabin photos of American’s 787-9s.
Incredible write up by Gary Leff on Flight 5342.
Remember, this life you are living has meaning. Thank you for reading. I am grateful you are here and would love to hear from you. If you'd like to write me a note, simply reply to this email. Otherwise I'll see you in the next one.

P.S. If I can ever help you plan your next travel adventure (slash help make your points go farther), I’d be delighted. You can schedule time together here.