Planning travel can sometimes feel like a part-time job—one involving twelve browser tabs, three price trackers, and a slow unraveling of your patience. KAYAK seems to have noticed. Just in time for the FIFA World Cup 2026 and the travel frenzy expected around host cities like Toronto and Vancouver, KAYAK has launched Ask AI, a new conversational planning tool designed to make travel booking feel a lot less chaotic.
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Think of it as traditional travel search…with a brain
Rather than bouncing between tabs comparing flights, hotels and rental cars, Ask AI lets travellers plan trips through a chat-style interface while live results update alongside the conversation. Ask about hotels near a stadium, compare flights between host cities, or map out a multi-city itinerary without restarting searches every time your plans change. And for anyone who has ever spiralled while trying to coordinate flights around tournament schedules, that sounds suspiciously appealing.
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A smarter way to plan
What makes Ask AI interesting isn’t just that it uses conversational AI—it’s that it combines it with real-time search functionality. You’re not getting vague travel inspiration or chatbot fluff. You’re getting live pricing, bookable options, and traditional filters working alongside a more intuitive planning experience.
According to Matthias Keller, Chief Product Officer at KAYAK, the idea grew out of how travellers are already behaving—using AI to begin planning, but still relying on conventional search tools to make decisions. Ask AI aims to collapse those two behaviours into one seamless process. And frankly, it makes sense.
Launching into a World Cup boom
The timing isn’t accidental. KAYAK data shows flight searches to Canadian World Cup host cities are already climbing, with Toronto up 19 per cent year-over-year and Vancouver up 5 per cent. Hotel prices are also rising sharply across host markets, with Canada seeing increases of 55 per cent. In other words: procrastinators, beware. To complement the new planning tool, KAYAK is also launching a World Cup Trends Dashboard, giving travellers real-time visibility into shifting prices, rising demand and destination search trends.
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The bigger picture
There’s a broader story here beyond football tourism. Ask AI signals how travel search is evolving—from keyword hunting to something more conversational, responsive and personalized. And if it can spare travellers from juggling ten tabs while trying to book a flight to Toronto, a hotel near the stadium and a rental car that doesn’t cost as much as a midfielder transfer fee, all the better. For World Cup travellers especially, it may prove to be the digital co-pilot they didn’t know they needed.
Feature image by Tony Schnagl
