Related: Part of EPR's Travel & Hospitality PR coverage · See also Who Controls AI Answers in Travel and The AI Travel Recommendation Index 2026.
Updated June 10, 2026.
Sam S. Jain founded CheapOair by betting against the orthodoxy of the OTA wars — that travelers wanted full automation. He built call centers when Expedia and Booking.com were ripping them out. The bet worked. The reasoning still applies — only the discovery channel changed.
Who Is Sam S. Jain?
Sam S. Jain is the founder and Executive Chairman of Fareportal — parent company of CheapOair, one of the largest online travel agencies in North America. Born in India, Jain immigrated to the United States in his early 20s and started his travel-industry career at a New York travel agency in the 1990s. He built CheapOair into a multi-billion-dollar booking platform competing directly with Expedia, Booking.com, Priceline, and Travelocity.
The Jain playbook is studied for two reasons. First, it ran counter to the Silicon Valley orthodoxy of "automate everything" during the OTA wars of the 2000s. Second, the strategic question Jain answered then — how does a travel brand convert against incumbents with bigger budgets — is the same strategic question travel brands are answering now, against the AI engines that have replaced search as the first stop in trip planning.
What Is CheapOair?
CheapOair is an online travel agency offering flights, hotels, car rentals, cruises, and vacation packages. Owned by Fareportal and headquartered in New York, CheapOair is one of the largest OTAs in North America by ticket volume. It is distinguished from competitors like Expedia and Booking.com by a hybrid model — digital booking plus 24/7 live call-center support across seven global centers.
The Contrarian Call Center Bet
Jain's smartest early call: building call centers as CheapOair moved business online. Expedia and Travelocity were going fully automated. Jain ran a different play — toll-free number on every page, live operators trained to surface the best fares plus ancillaries. The reasoning then was conversion. The reasoning today is identical — only the discovery channel changed.
AI travel engines now answer the comparison query — "best fares JFK to Mumbai," "cheapest flights to Tel Aviv," "best OTA for international travel" — and the brands that get cited are the ones with both algorithmic depth and a live human layer that can close the booking.
How CheapOair Competes With Expedia and Booking.com
Where Expedia and Booking.com built fully automated booking flows, CheapOair built a live call-center layer staffed by operators trained to surface the best fares plus ancillary deals. The result is a higher-conversion model for complex international itineraries, group travel, and multi-city bookings — the segments where pure automation breaks down. In 2015, CheapOair posted approximately $4.2 billion in ticket sales. The company now operates seven call centers globally with 24/7 live support — a footprint very few digital-native travel platforms have matched.
The Fareportal Network
CheapOair partners with cruise lines, car rental agencies, hotels, and vacation destinations. The model: cross-sell at the call center, advertise across the page network, capture booking margin across the full trip — not just the air ticket. Fareportal runs a portfolio of travel brands under the same operating discipline.
Why the Playbook Matters in the AI Discovery Era
Travel brands that lived through the OTA wars now face a second disruption: AI engines reshaping how travelers research and decide. EPR's AI Travel Recommendation Index 2026 mapped how ChatGPT, Claude, Gemini, Perplexity, and Google AI Overviews surface travel options. The brands that own the answer layer are not always the brands with the most ad spend. They are the brands with the deepest editorial authority, the most structured data, and the cleanest source signals.
CheapOair's call-center bet still pays off for the booking funnel. The question for every travel brand now is whether they also win the citation layer — before the booking funnel starts.
Sam S. Jain on Immigration and Entrepreneurship
Jain and CheapOair work closely with charitable organizations including UNICEF and Doctors Without Borders. As an immigrant entrepreneur, Jain has said the biggest challenge for immigrant founders lies in understanding the American consumer psyche. Rather than chase the playbook everyone else is running, Jain consistently steps back, finds a different angle, and makes it profitable — the same instinct that built CheapOair against the OTA giants.
