[Hoja Verdes]

Don't just blindly choose the least expensive flight, you always need to compare price to total trip duration. Trip duration is the total time the trip will take, including stops, plane changes, and layovers, from the moment your first flight departs until the moment your final flight arrives at your destination.

For example, I was looking at flights from ATL to San Jose last week and noticed that there were 3 flights in the same general price range, i.e. $450, $500, and $600. If you're not careful, you might see that they all depart about the same time and blindly select the $450 flight due to price alone. But upon closer inspection, I saw that the total trip duration of the $450 flight was a whopping 20 hours!! Whereas the other two flights, only $100-$150 more (respectively) were both about 6 hours total. I think it goes without saying that spending an additional $100 is well worth it when compared to sitting in airport terminals for an extra 8 hours to/from your vacation.

Also be aware of the same thing on your return flight, as well as what time the flight leaves San Jose. I can tell you from experience that many times I've seen a flight that leaves at 10am on a Sunday and thought to myself "ahh, that's plenty of time to wake up that morning and still have a good time Saturday night." Then when that morning rolls around, once you factor in getting to the airport early in a foreign unfamiliar city, you find that not only are you having to wake up at 6am Sunday morning, but you're also getting a little anxiety starting at about 11pm on Saturday night b/c you know you have to wake up in 7 hours. Instead, I'd recommend booking a return flight no earlier than about 2pm if possible. That way, you can enjoy yourself Saturday night, sleep late, take your time packing up and getting something to eat, and still make it to the airport at noon. Sure, you may get home late at night, but I'm usually more likely to sleep on an afternoon/evening flight than I am on one early in the morning. Tend to be less hungover as well, or if you're like me, you can just start drinking again and don't feel like a degenerate drinking on the early flight.

[pavyracer]

Booking a 20 hr flight instead of a 6 hr flight to save a few bucks is a -EV play.

[sickler]

Booking a 20 hr flight instead of a 6 hr flight to save a few bucks is a -EV play.

Time is money

[BetterBizness]

Booking a 20 hr flight instead of a 6 hr flight to save a few bucks is a -EV play.

how about if you have an escort waiting for you in Each city? Still -EV?