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Kayak was founded in January 2004 by Paul M. English and Steve Hafner, a co-founder of Orbitz, under the name Travel Search Company Inc. It became Kayak Software Corporation in August 2004 and launched its site in February 2005. Unlike an online travel agency that handles bookings and customer service, Kayak set out to be a metasearch engine that pulls fares from other sites. In December 2007 it raised $196 million from General Catalyst, Sequoia Capital, Accel Partners and Oak Investment Partners and bought its rival SideStep. It then expanded in Europe, buying the German search site Swoodoo in 2010 and Austria’s checkfelix in 2011, and in January 2011 shut SideStep down and redirected its traffic to kayak.com.

In December 2011 Kayak said it would not renew its advertising on the TLC reality show All-American Muslim after a campaign by the Florida Family Association; chief marketing officer Robert Birge said TLC had not been upfront about the nature of the show. Kayak went public on the Nasdaq on July 20, 2012 under the ticker KYAK, opening at $26 and closing its first day at $33.18. In May 2013 Priceline.com, now Booking Holdings, bought Kayak for $2.1 billion. Kayak now operates in 30 countries and about 20 languages.

• Under Booking Holdings, Kayak added Momondo, Cheapflights, HotelsCombined and the Brazilian company Mundi.
• Kayak launched voice search on Amazon Alexa in 2016.
• It released a ChatGPT plugin in 2023 and added AI recommendations and price checking in 2024.
• Southwest Airlines fares were added to Kayak in 2024.
• A chat-based Kayak.ai beta launched in April 2025, followed by a conversational AI mode built into the main platform in October 2026.