Hipmunk Co-Founders Debut Next-Gen Flight Search Tool to Skirt Online Travel ‘Collusion’

Think of it as an online travel confessional, and a make-good project. The co-founders of flight search engine Hipmunk, a darling of Silicon Valley and flight power users until its demise last year, have debuted a next-generation flight search tool that seeks to sidestep the partner “collusion” that is rife in online travel.

Hipmunk co-founders Adam Goldstein, an angel investor, and Steve Huffman, who’s the Reddit CEO, provided seed funding for Flight Penguin, and vow to take zero money in commissions or incentives from airlines, online travel agencies or anyone else — except subscribers to their new $10 per month service.

Don’t look for a functional website or a mobile app; the Flight Penguin link above merely goes to an informational landing and registration page. Flight Penguin will operate by design as a Chrome extension, taking a page from a browser-based plug-in that metasearch pioneer Sidestep likewise initially offered more than two decades ago.

One of the reasons for the Chrome extension is that users perform the searches on airline, online travel agency, metasearch, and consolidator websites from their own computing devices, and not from servers in a Flight Penguin office. In this way, subscribers using Flight Penguin can search and retrieve fares on Southwest Airlines, for example, even though most online travel players are barred from doing so and would trigger a cease and desist letter from the prickly airline if they did.

Flight Penguin provides users with so-called “deep links” so they can book the flights on the airline or online travel agency websites.

Goldstein told Skift the use of the browser extension means there is no middleman so it avoids the frequent online travel problem where a metasearch site might display a fare, but when users click over to a supplier partner, the fare may be higher or the flight no longer available.

As with Hipmunk, which was founded in 2010 and sought to show the flight options with the least “agony,” or “suckage,” as they originally wanted to label it, Flight Penguin tries to enable travelers to fly “pain-free” with the most convenient or comfortable flights that have the best value.

In a mea culpa of sorts, Goldstein acknowledged that online travel sites distort the way they show flights to users based on the commissions and incentives they receive, and Hipmunk was guilty of some of the same practices.

For example, many metasearch sites agree to airline mandates to show only one airline fare per grid — no side by side comparisons — and frequently won’t show a lower fare even if it’s available, Goldstein said.

As it did during the early days of Hipmunk, Flight Penguin takes a shot at Kayak. The Flight Penguin landing page states, “It’s time to put Kayak on ice. Take the pain out of flight search. Built by some of the same people who built Hipmunk, Flight Penguin is now available as a Chrome extension.”

The person responsible for writing most of the Flight Penguin code is Sheri Zada, who worked as a Hipmunk developer for nearly four years.

There is a waiting list to get access to the Flight Penguin Chrome extension so we couldn’t try it ourselves before writing this story. But Flight Penguin sent us a screenshot of a Dallas to Boston search for an April 12 flight.

Among the most convenient flights that Flight Penguin displays in its search results for this query are a variety of American Airlines flights from Dallas for $246 that land in Boston in the early afternoon or late evening.

We decided to compare it to a similar search on Kayak, and you immediately notice how Kayak’s search results are cluttered with ads from Delta and Walt Disney World, for example.

Below a Delta advertisement, the first result Kayak shows is a $66 Spirit fare from FareScan, but the Dallas to Boston flight has a not-so-convenient stopover in Orlando.

In another dig at rivals, Flight Penguin states: “Unlike other travel services, Flight Penguin won’t sell you to the highest bidder. Our results are unbiased and uncorrupted.”

Incidentally, why is the tool called Flight Penguin? Goldstein said the founders wanted a recognizable logo, and thought it would be funny because penguins can’t fly.

In 2016, SAP-Concur acquired Hipmunk, and vowed to use it as the basis for a business fare search tool. That development took place for some time, but SAP mothballed the site early in 2020, and refused the pleas of Hipmunk’s co-founders to reclaim the brand and technology.

Goldstein said Sunday that Flight Penguin grew out of a “crying session” among former Hipmunk employees after the shutdown, and some of the ex-staffers decided to build an improved successor.

Goldstein said the meeting attendees thought it would be important to give those “millions” of former Hipmunk fans the opportunity to use an unbiased flight search tool when travel recovers. He said that is especially important today because of airline and online travel agency consolidation, including the fact that some online travel agencies also own metasearch businesses, and thus exacerbating opportunities for bias.

Flight Penguin users can perform flight searches and view results for paying with cash or Chase Ultimate Rewards points. Goldstein said Chase cardholders tend to overlap with the former Hipmunk base, and that Flight Penguin plans to add other cards and points at a later time.

The Chrome extension, which does some international searches but is skewed toward domestic U.S. queries for now, has been in beta among friends and family for a couple of months.

Flight Penguin likely has only a handful of employees, no publicly named executives, and is really a side gig for Goldstein, who serves on boards and does angel investing, and his peers. Huffman is busy running Reddit. There is no venture capital funding, and not much of a marketing budget, either.

There are no plans at this juncture to scale up Flight Penguin with a massive search engine marketing campaign. Goldstein said its backers and fans aren’t sure whether it would succeed as a viable business, and and want to see how things evolve.

He acknowledged that the subscription service, with a 30-day free trial and then $10 per month, skews toward frequent travelers, and thus limits its potential base. If you take at least five flights per year then a subscription would be worth the money, Goldstein said, noting that if you fly once or twice annually than it probably wouldn’t be.

But one thing that’s clear: the Hipmunk crew is back, taking shots at Kayak, and they are doing their own thing.

Photo Credit: A file photo of a couple in coach class on Hawaiian Airlines. Flight Penguin intends to help subscribes search and book the most convenient flights. Hawaiian Airlines

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