AI / MACHINE LEARNING

KAYAK Introduces AI Mode: Conversational Travel Search, Just in Time for Holiday Planning

KAYAK has launched KAYAK.ai, an AI-powered conversational travel search tool that simplifies trip planning through natural-language interaction, offering real-time results and setting a new standard for personalized, loyalty-driven travel experiences.

(Image Source)

GLO

From Keywords to Conversation

As the holiday travel rush approaches, KAYAK is rolling out a powerful new tool designed to simplify the planning process. Called KAYAK.ai, the platform steps beyond traditional search bars and lets users engage in natural-language conversations to discover flights, hotels, and full itineraries — all with real-time pricing and tailored suggestions.

Travel search has long relied on rigid filters and manual input, which often made trip planning feel more mechanical than exciting. With KAYAK.ai, users can simply ask questions like “What’s the best nonstop flight from London to New York in December under £500?” or “We need a family-friendly beach resort, flights from Manchester, early July, budget £1,200 for four.” In response, the AI uses data from hundreds of providers and real-time analytics to deliver curated results in an easy conversational format.

Key features include:

• Real-time pricing rather than outdated or cached data.

• Conversational follow-up, allowing users to refine their search naturally (e.g., “Show only rooms with free breakfast and pool”).

• Continuous evolution, as KAYAK describes the tool as a living test lab whose features will roll out to the full site once refined.

• Business travel integration, with KAYAK for Business set to receive AI-powered capabilities later in the year.

Why It Matters for Holiday Planning

The timing of the release is no coincidence. As travelers prepare for peak holiday season, many face rising prices, limited availability, and tighter planning windows. Traditional multi-step search processes — flights, hotels, cars, and reviews across multiple tabs — often lead to frustration. KAYAK.ai aims to streamline all of that into a single conversation.

For travelers, the benefits are clear:

• Speed – No more juggling tabs or filters; one query delivers everything.

• Flexibility – The system understands open-ended requests like “Best long-weekend getaway from Glasgow for two under £800.”

• Confidence – With live pricing and verified provider data, users can trust the results.

• Exploration – You don’t have to know your exact dates; simply say “sometime after Christmas” and the AI will suggest options.

For KAYAK, this also positions the company to capture travelers earlier in their planning journey. Instead of waiting until users know exact dates and routes, KAYAK can now engage at the inspiration stage — when intent is forming and loyalty can be built.

Challenges and Considerations

As with any new AI-driven tool, KAYAK faces a few key challenges:

• Accuracy and trust – Travelers expect real-time data to be consistent across search, booking, and checkout.

• User familiarity – Some users may still prefer the comfort of traditional search bars.

• Privacy and loyalty integration – Merging personal data, frequent flyer details, and loyalty rewards into conversational AI will require strong safeguards.

• End-to-end automation – While conversational discovery is live, full booking automation is still developing.

What to Expect Next

KAYAK.ai is expected to expand rapidly over the coming months, with goals to:

• Add multilingual and regional support.

• Integrate adjacent services like car rentals, insurance, and activities.

• Enable complete bookings directly within chat.

• Incorporate personalization and loyalty recognition for returning users.

• Extend the tool to corporate travelers seeking faster, policy-compliant bookings.

Global Loyalty Organisation Take

From a global loyalty perspective, KAYAK.ai represents a turning point in how travelers interact with booking platforms and rewards ecosystems. Conversational AI transforms the search process from a transaction into a dialogue — and that’s where brand loyalty is truly built. By meeting customers at the earliest stage of planning, KAYAK positions itself as a trusted travel companion rather than just a price aggregator.

For loyalty organizations worldwide, the opportunity lies in integration: connecting points systems, elite benefits, and personalized offers into a conversational interface that feels effortless. Those who adapt quickly will strengthen engagement and emotional connection with travelers; those who don’t risk becoming invisible behind the AI intermediaries that now shape the modern booking journey.

Source: KAYAK