11.25
I travel quite a bit and my favorite site to use is Kayak. It has a lot of features that make it the easiest to use and best airfare search out there. Within the last year, Kayak implemented a feature that allows you to search for airfare using flexible dates. Many times I’m traveling somewhere and I just want the lowest fare within a 3 or 4 day window. Perfect, I don’t have to load up 8 windows and toggle back and forth to find the lowest airfare.
I live in Salt Lake City, and every year I travel to somewhere far away from SLC for a few weeks of vacation. In this case, I’m traveling to Saigon (Ho Chi Minh City) right after Christmas. I’m somewhat flexible on my dates since it is a vacation, so I decided to give the flexible dates feature a whirl to find me the lowest airfare.

The expected result is that this will produce the same results as searching for SLC -> SGN departing on Dec 26 and returning on any of the following days: Jan 09, 10, 11, 12, 13, 14 or 15.
Here are the prices broken down by day on the results page:

The results seemed odd. Why would Jan 12 be ~$700 cheaper than returning Jan 13? And returning Jan 11 would be almost 3 grand? That didn’t seem to make sense, so I did a regular search on Kayak departing Dec 26 and returning Jan 13. Below is the result for that search.
The actual cheapest roundtrip airfare for that itinerary: $1565. A difference of about $500.
I did a search departing on Dec 26 and returning Jan 11, the one that should cost almost 3 grand. Actual cheapest cost: $1678. That’s a difference of about $1300.
That’s a massive price difference for those days.
Shouldn’t the prices be the same whether I use the flexible dates feature or search for the days individually? Clearly they’re not.
So what’s going on here?
After some sleuthing it became apparent what was going on. Whether or not this is entirely Kayak’s fault is up for debate, but what happens is that when you search for a flight departing on let’s say Dec 26 and returning Jan 12, you get exactly that result. Kayak goes and searches all the travel websites with those parameters. When you choose the flexible dates feature, it does not, in fact launch parallel searches and aggregate the results as expected. Instead, it takes the results of your base search dates (Dec 26 -> Jan 12), and then asks the travel websites if any of the results are also available on other days. Since itineraries are often bundled together when you search for them by 3rd party companies like cheaptickets.com, what you get is the cheapest available itinerary that is available on your base date and available on one of your flexible dates. Usually the only places that have identical itineraries from day to day are the actual airline websites, so the prices are almost always higher using the flexible dates feature. From a user perspective it doesn’t make any sense, but from Kayak’s perspective it makes sense since it saves them from having to perform extra searches (searches cost them $$$). Kayak should seriously consider revamping this feature to actually perform parallel searches, or make it clear that the flexible dates feature is not the same as searching for the days individually.
Summary:
Using Kayak.com’s flexible dates feature does not give you the same results as searching for your itinerary on the days individually. Often it will be more expensive, sometimes a lot more expensive.
Update:
Kayak’s CTO says improvements are coming to the flexible dates feature. He also says they’ll try to make the user interface more clear on this issue.