Frequent Miler on the Air · Monday, August 10, 2026
The team discusses whether to book non-points-savvy travel companions in economy or business class, or the cheapest/nicest rooms. Greg explains his approach is usually to match what he's paying, whether cash or points, but acknowledges that significant point value upgrades might be considered if the flight is long enough.
“Well, it depends. It really does. Um, if I'm traveling with my wife and kids and we're going to Europe and, you know, if I'm paying cash for a business class ticket, then it only makes sense that they would have business class tickets. And if I'm paying cash for an economy ticket, then they get an economy ticket.”
“Now if I'm trying to use points to book us all, then I have to take into consideration how many points it's going to cost me. Um, and, and what the value is. So, um, if I have a lot of points and it's a significant upgrade from economy to business, then I'll do it. But if it's a situation where, you know, it's a very short flight, or if it's a situation where, you know, it's not that big of an upgrade, then I'll just book everybody in economy.”