In a March appearance at Oxford Union, Chesky said he wants Airbnb "to one day redefine how we fly." Then he added, "The funny thing about flying is, no matter how successful you are in life, you are reminded how much of a mere mortal you are, [so] that's another area we really want to invest in."
The flight-booking space is tough, with lower margins than hotel and car rentals, and airlines tightly controlling inventory. But it could be a natural stepping stone to the greater online travel agency market, where Airbnb can try to preserve its incredibly fast growth story as it pursues an eventual IPO.
"In the flight-booking area in general, the obvious [thing missing] is also one that plagues hotels, which is, everything is the same; there is no differentiator," said Douglas Quinby, senior vice president of research at Phocuswright. "The airlines have tried hard to differentiate by adding different types of fare bundles or services, but right now the shopping experience across airlines is commoditized and price-driven."
Big online travel agencies are moving in on Airbnb's turf as well. In the most recent quarter, Priceline's Booking.com offered roughly 650,000 "alternative lodging" properties — many which include multiple listings — an increase of more than 50 percent from a year before. Priceline's valuation of $89 billion is bigger than both Marriott and Airbnb combined.
Expedia said its alternative lodging subsidiary, HomeAway, experienced 30 percent growth in the most recent quarter. It has 1.4 million listings.
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Airbnb is considering different options for breaking into the market, including acquiring an online travel agency.
"They bring their massive base of users to the arena — that's big," said Dennis Schaal, executive editor of Skift, an online hub for travel news and research. "They could bring a local flavor to flights, combining them with a stay at an Airbnb, but the flight business is hard. You have to build a customer service department, deal with canceled flights and rebooking passengers. Does Airbnb really want to get into that? It'll take their focus off their core business as well."