• Tommy Obenchain
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  • Why I Still Book Flights the Old-Fashioned Way (Sometimes)

Why I Still Book Flights the Old-Fashioned Way (Sometimes)

Points, perks, and peace of mind—here’s when booking direct still makes sense👇🏼

Friends,

With all the tools, search engines, and third-party booking sites out there, it’s easy to forget just how solid an airline’s own website can be.

I don’t mean to sound nostalgic. Booking through airline portals can still feel clunky. Some of them look like they haven’t been updated since the Obama administration. But here’s the thing: sometimes it really is the smartest move—and not just because of loyalty or points.

For me, the process usually starts with Google Flights. It’s still the fastest way to scan for lowest fares, see alternate airports, and map out date flexibility. But once I’ve found what I’m looking for? I almost always go book it directly through the airline’s site or app.

Here’s why:

1. Loyalty is real—and it starts with credit
If you care about elite status (and I generally do), booking directly with an airline is the way to go. Many carriers only credit elite-qualifying miles and dollars when you book direct or through an approved agency. OTA bookings? You’ll often still get the miles—but not always the credit that actually gets you status.

That counts if you’re chasing upgrades, free bags, or priority boarding.

2. When things go wrong, the airline can actually help
One of the biggest headaches when booking through OTAs is what happens during IRROPS (industry shorthand for irregular operations: delays, cancellations, rebookings).

If you booked through Expedia or Priceline, the airline might send you back to them to fix it. But if you booked direct? You’re their customer. That means gate agents and call center reps are often more empowered to help.

And when you’re stranded somewhere or are faced with an unexpected schedule change, that distinction is material. It’s equally material with more trivial items like making a fast change, pre-selecting a seat, or checking upgrade options.

3. Sometimes the best fares are hiding in plain sight
Not always—but sometimes. Airlines do run direct-only sales, especially for flash promos or route launches.

This is fairly niche, but can be worth it in many cases.

4. When I don’t book through the airline
Of course, there are times when I will not use the airline portal.

If I’m piecing together a multi-airline itinerary (especially on different alliances), or hunting down a unique carrier or obscure route (think Mongolian Airlines from Istanbul to Ulaanbaatar), I’m probably using a search engine or specialty OTA.

Same goes for mixed-cabin fares that don’t show up properly on most airline sites—like when you can fly lie-flat to Europe but connect onward in economy for half the price.

So I’m not anti-OTA. I’m pro context. Or something like that.

Bottom line
I use whatever tool fits the trip. But more often than not, that looks like searching smart (Google Flights) and booking smart (direct).

Airline portals are worthwhile—especially when status credit, service, or post-booking flexibility matters.

Fly well.

NEWS

Some US carriers are charging more for solo travelers, and Gary Leff has the scoop.

Official press release for American’s innovative OSS program.

More on AI pricing.

Fly well.