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Online Travel Faces the Next Phase of AI Commercialization

Good Sunday morning from Seattle . . . Our weekly Online Travel Update for the week ending Friday, April 24, is below. It was another interesting week at Booking.com (second in a row) as it faces yet another competition law inquiry – this time from Italian competition authorities over the preferential treatment provided properties in Booking.com’s preferred program. AI regulation also features prominently in this week’s Update as regulators press ahead with restrictions on technology based or assisted pricing. Enjoy.

    • Another Week; Another AI Partnership Announcement. The AI arms race continues. This past week featured another newly announced “AI partnership” between an established intermediary and a large AI platform. This week’s announcement came out of TripAdvisor - one of the very earliest intermediaries to announce an AI partnership with Perplexity. This time TripAdvisor has partnered with Anthropic to make its hotel and experiences inventories available to users of Claude. Claude users can now summon TripAdvisor content by identifying Viator or TripAdvisor as their travel partner. When users are ready to book recommended travel, Claude re-directs them back to TripAdvisor to complete the booking. TripAdvisor also announced last week an expanded partnership with Amazon to assist users of Amazon’s Alexa+ to build travel and modify travel itineraries via voice.
    • OpenAI Adopts Familiar Advertising Pricing Model. According to third party sources, OpenAI has adopted a widely used search advertising payment model – pay per click (PPC) – for its AI chatbot, ChatGPT. Pay per click is the same model used by Google and has become the online marketing industry’s standard. What is a ChatGPT generated click really worth? The market will soon tell us. According to several sources, travel advertising is now routinely appearing on ChatGPT with, wait, you guessed it, OTAs, absolutely dominating the platform (Expedia, Booking.com and Airbnb featured in over 80% of the noted ads). What triggers these ads and to what extent are they tied to specific indicia of users’ intent remains to be seen.
    • Booking.com’s Preferred Program Under Scrutiny. To what extent is a program that allegedly values the commissions paid by suppliers over other consumer oriented factors (quality or value) anti-competitive? That’s the question now before Italian regulators. We will keep an eye on this one. Perhaps regulators will also address the question of what value is a program the purports to offer preferred placement if every competitor is effectively “required” to be part of the same program? What does “preferred” really mean?
    • AI Regulation on the Horizon? For some time now my answer to the often repeated question, “What AI regulations apply to my hospitality operation?” has largely been the same. Not many. Outside the possible use of AI systems in certain “high-risk” decision making (almost exclusively in the employment context for most hospitality operators) or such systems’ access and use of personal information, most of the AI regulations (even outside the U.S.) proposed or adopted over the past few years have had little application. That may soon change. Possible changes in the EU and at the state level may introduce a new era of regulation. At the top of legislators’ and regulators’ minds? Algorithmic or technology assisted pricing. While Maryland’s first of its kind anti-surveillance pricing legislation may specifically exempt the kind of widely used loyalty program or membership pricing often used in the hospitality industry, not all states considering the issue may include similar carve outs.

Have a great week everyone.


Tripadvisor, Viator Expand AI Partnerships with Claude, Alexa+
April 24, 2026 via PhocusWire
Tripadvisor and Viator have launched in Anthropic's artificial intelligence chatbot Claude. The companies have also expanded their partnership with Amazon, including a voice search feature in Alexa+.

Capital One Closed Hopper Tech and Employee Deal in April, Focuses on Travel Expansion
April 22, 2026 via Skift
The Hopper tech acquisition, along with that of Discover and Brex, position Capital One Travel to get much more competitive with American Express and Chase Travel in going after luxury and business travelers.

ChatGPT Just Turned On the Pricing Model Travel Advertising Runs On
April 22, 2026 via Skift
Per-click pricing is the advertising auction travel already competes in. ChatGPT just pulled up a chair.

Booking.com Hit With Italy Antitrust Probe Over Hotel Visibility
April 22, 2026 via Skift
This is the second investigation by Italy's regulators into Booking.com's competitive practices.

EU Moves to Tighten AI Regulation, Adding New Compliance Pressure for Hotels
April 22, 2026 via Hotel News Resource
European plans to tighten regulation of artificial intelligence systems could introduce new compliance requirements for hotel operators, as the industry increasingly integrates AI into pricing, marketing, and customer service functions.

Italian Antitrust Opens Investigation into Booking.com
April 22, 2026 via ANSA
The Italian Antitrust Authority said Wednesday that it has opened an investigation into Booking.com for alleged unfair commercial practices.

Maryland Becomes First State to Pass Bill Banning ‘Surveillance Pricing’
April 21, 2026 via 23ABC
Maryland is poised to become the first state in the country to ban "surveillance pricing." The practice refers to companies using a shopper’s personal data, such as browsing history, location, or purchasing behavior, to tailor prices to individual customers.

  • Greg  Duff
    Principal

    Greg is Chair of the firm's national Hospitality, Travel & Tourism practice, which is directed at the variety of matters faced by hospitality and travel industry members, including purchase and sales agreements, management ...

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About the Editor

Greg Duff founded and chairs Foster Garvey’s national Hospitality, Travel & Tourism group. His practice largely focuses on operations-oriented matters faced by hospitality industry members, including sales and marketing, distribution and e-commerce, procurement and technology. Greg also serves as counsel and legal advisor to many of the hospitality industry’s associations and trade groups, including AH&LA, HFTP and HSMAI.

His popular weekly digest, Online Travel Update, offers a global perspective of key trends and issues at the intersection of the hospitality, online travel and technology arenas. Since 2019, Greg has been recognized among JD Supra’s Top Authors in its annual Readers’ Choice Awards for Airlines/Aviation, Transportation and Artificial Intelligence, including being named the content platform’s #1 Author for Transportation in 2021.

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