Hipmunk’s founders launch Flight Penguin to bring back Hipmunk-style flight search

Hipmunk’s founders are building a successor to their now-defunct flight search service.

The startup was acquired by SAP-owned travel and expense platform Concur in 2016, and its CEO Adam Goldstein departed in 2018. But Goldstein told me he and his co-founder Steve Huffman (also co-founder and CEO of Reddit) were still disappointed when Concur shut the service down at the beginning of last year.

“Over the years, there were millions and millions of people who used it and loved it,” Goldstein said. (I was one of those people — even before I knew what he was working on, I started out our call by telling Goldstein how much I miss Hipmunk.)

So the pair seed funded a project called Flight Penguin, with Goldstein serving as the new company’s chairman. And he said the actual product was built by former Hipmunk developer Sheri Zada.

The Flight Penguin interface will be very familiar to old Hipmunk users, with a visual layout that makes it easy to see the timing of flights and length of layovers. And just as Hipmunk allowed users to organize results by “agony” (so that the top results aren’t just cheap flights with inconvenient timing or ridiculous layovers), Flight Penguin allows them to sort their flights by “pain.”

Image Credits: Flight Penguin

But this isn’t just the old experience with a fresh coat of paint — it’s also meant to improve on Hipmunk in a few key ways. For one thing, it allows users to search by Chase Ultimate Rewards Points (as well as U.S. dollars, with the goal of adding more currencies and rewards programs in the future).

And the product itself is a Google Chrome extension, rather than a traditional flight search website. The extension actually presents a full, standalone web experience (rather than an overlay on another website), but Goldstein said this approach is still important, because it allows Flight Penguin to pull its data “through the frontend instead of the backend,” giving it the most up-to-date information. This helps to avoid situations where a flight or price shows up in search results but isn’t available on the airline’s or other seller’s website.

In addition, Goldstein said Flight Penguin will show “all the flights.” In other words, it won’t be making any deals with the airlines to hide certain flights or prices, and it will also show airlines that don’t normally make their flights available on other search platforms.

“There are actually many, many flights available but consumers don’t see them because travel search sites work out these deals,” he said. “We’re choosing not to play that game.”

That has the obvious benefit of offering more comprehensive results, but also the disadvantage that Flight Penguin will not be able to collect affiliate fees for flight purchases. Instead, after a 30-day trial period, it will charge users $10 per month. (This is an introductory fee and will likely change in the future.)

Goldstein acknowledged that this is probably “not going to be a mainstream product that 50 million Americans use,” but he’s hoping that it can attract a significant subscriber base of frequent travelers who “value their time and care about the flight booking experience.”

“What we learned from Hipmunk was […] the way business has traditionally been done in online travel worked for consumers in an era with lots of competition between airlines and travel agencies,” he added. “In a world where there’s much less competition, you’re basically becoming an agent for the people you’re working with, and it’s hard to build a business model around providing a great user experience. That’s why we’re saying that we’re going to opt out of this game and play by our own rules.”

Flight Penguin is currently accepting signups for its waitlist, but Goldstein said the company is simply using this to bring users on-board in a controlled fashion, and that it plans to move people off the wait list pretty quickly.