Expedia’s 23-Year Evolution in Online Travel

Pioneering travel technology company Expedia is undergoing a huge change in leadership, as former CEO Mark Okerstrom and former Chief Financial Officer Alan Pickerill announced their resignations Wednesday. Launched in the 1990s, Expedia soon became one of the first successful online travel agencies, acting as a business model for legions of travel sites that came afterward. We take a look back at how the travel agency grew over the years, expanding into nearly every corner of the travel search market.

October 1996 — Expedia was founded as a division of Microsoft.

September 1999 — Expedia was spun off as its own company.

July 2001 — IAC/InterActiveCorp, a U.S.-based holding company, bought a controlling interest in Expedia for $1.5 billion.

August 2005 — IAC/InterActiveCorp spun off Expedia, Inc. This included its group of travel businesses, Expedia, Egencia, TripAdvisor, Classic Vacations, eLong, Hotels.com, and Hotwire.com.

August 2005 — Dara Khosrowshahi, formerly the chief financial officer at IAC/InterActiveCorp, became CEO of Expedia. Barry Diller resigned as CEO of IAC/InterActiveCorp, but retained a controlling interest in Expedia. He remains chairman of IAC, the company he founded.

March 2011 — Expedia Inc. launched its first mobile app, called TripAssist.

December 2011 — Expedia, Inc. spun out TripAdvisor Media Group, retaining its portfolio of travel transaction brands.

December 2012 — Expedia bought a majority stake in travel search engine Trivago for €477 million (about $529 million).

March 2012 — Expedia’s Egencia acquired Via Travel, the largest travel company in Norway.

July 2014 — Expedia acquired Australian booking site Wotif for $658 million.

January 2015 — Expedia acquired online travel agency Travelocity from Sabre Corporation for $280 million.

February 2015 — Expedia acquired travel fare aggregator Orbitz for $1.2 billion.

November 2015 — Expedia acquired vacation rental company HomeAway. This deal included all of HomeAway’s global brands: VRBO, HomeAway.com, and VacationRentals.com

August 2017 — Khosrowshahi announced he would be resigning as CEO. Later that month, Mark Okerstrom stepped in as CEO of Expedia, Inc.

March 2018 — Expedia, Inc. announced that it had changed its name to Expedia Group, Inc.

October 2018 — Expedia bought Pillow and ApartmentJet, two startups that help landlords convert apartments into short-term rentals.

March 2019 — Expedia rebranded HomeAway as Vrbo (pronounced VER-boh).

December 2019 — Expedia CEO Mark Okerstrom and Chief Financial Officer Alan Pickerill resigned.

Sources: Skift, Wikipedia