The single-worst airplane ride I ever took was the red eye out of Vegas on a Sunday night — I left at like 9:00 PM Vegas time and landed in Charlotte at 6:00 AM EST (where I had to drive to work, guh). Of course, it was made way worse by the fact that I sat next to a woman who weighed about 450 pounds and snacked on Cheesy Poofs all GD night long.
But that was kind of unavoidable, unlike other nasty travel issues like delays, etc.
Enter Hipmunk, which has introduced an “agony rating” for various flights.
The iPhone app, which launched yesterday, sorts flights not just by price and departure time and all the normal stuff, but also by “agony.”
It’s a combination of factors that gives a certain flight the “agony rating” including number of layovers, duration of layover, length of flight and whatnot.
Let’s see what a flight to my bachelor party — wanna come??? — would sort out like right now if you were trying to book today, based on price:
$373 is a pretty good cost for a flight from Charlotte to Vegas, but there might be other factors to consider, right?
Let’s see how these flights shake out via the agony meter:

See how totally different that is from when you sort by flight? The cheapest option offered — the $373 US Airways flight — actually ranks as the fifth-most desirable flight because it’s kind of brutal.
My best guess is that’s because you fly out of Greensboro at 5:30 AM (UGH), and there’s a layover in Charlotte for more than an hour.
Scroll a little further down and you can find an option to Vegas for the same price that doesn’t land in Vegas until 9:30 at night and features a brutal two-hour, 44-minute layover in Charlotte.
These are all things we KNOW, but stuff that’s terrible to sort through when you use Kayak or some other search engine.
Hipmunk, though it won’t let you book online — a tremendous drawback — at the moment, takes a list of flights, pretends its using your brain to analyze which ones are terrible, and then sorts the results in pretty color-coded answers.
Hopefully, at some point they’ll offer booking services. Or, at the very least, a rapid chipmunk with aviator glasses who will gleefully murder any fatties who dare to stroll onto a red-eye flight with a crunchy, powder-covered cheese snack.










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