Hipmunk incorporates many of Kayak’s features, including alerts, along with a welcome dose of humor (it rates flights in terms of “Agony” — a combination of price, number of stops and total travel time). It also searches Amtrak routes when applicable, and Airbnb listings when you conduct a hotel search. Its flight search interface can be slightly confusing (sometimes it’s hard to tell which airline you’re selecting), but its other benefits make it a viable option.
I researched a long-weekend trip from New York City to Chicago from May 26 to 29 using those three sites, as well as individual airline sites. Travelocity offered a fare of $338 for a flight leaving Kennedy Airport around 7 a.m. on Delta and getting back into La Guardia on Spirit Airlines at 9 a.m. on Monday. (For the Spirit-averse, there was an option to bring you back into Newark on United for an additional $6.)
Kayak’s lowest advertised flight was on Delta for $362, a notable difference. (Kayak also offers “hacker fares” — flying different legs of a round-trip flight on different airlines — but I couldn’t even find the flight that Travelocity offered me on Kayak.) Hipmunk’s lowest advertised flight was an all-Spirit flight from La Guardia to O’Hare and back for $372.
Things got interesting when I searched on the airlines’ websites. The Delta flight Kayak offered me was the same price on the Delta site. With Spirit, though, things were a little wonky. The Travelocity flight that had one Delta leg and one Spirit leg cost just $269 if I booked the individual legs on the Delta and Spirit websites, respectively: saving $69. There was also a big difference with the Spirit flight Hipmunk offered: If booked directly on the Spirit site, the same flight cost $65 less.
It’s important to note that Southwest and its system, which allows for many nonstop routes other airlines don’t offer, won’t show its prices on the major search sites; the airline notoriously disallows third parties seeking to monitor its fares. In this scenario, that meant I had to go to Southwest’s site to find a round-trip package for an impressive $296, which includes two checked bags and no change fees.
Flights are travel sites’ bread and butter, right? Wrong. Hotels are where the money is. A 2013 Forbes article noted that an astounding 97 percent of Priceline’s revenue came from hotel bookings. Booking.com, which is owned by Priceline, is a big revenue driver and is able to do an enormous volume, as the company doesn’t act as the merchant of record. It simply connects guests with hotels and takes a fee.
Let’s get back to our long weekend in Chicago: Hotel selection is a bit more subjective, as more criteria are involved. I searched for a room for two at a four-star property downtown. Travelocity’s first nonsponsored recommendation was a room with a king bed at the Hard Rock Hotel Chicago, a decent choice, for $149 per…