The IT Nerd

KAYAK today introduced Ask AI, a new conversational travel planning experience designed to help travellers search, compare, and book trips more easily, as interest surges ahead of this summer’s World Cup.

Building on KAYAK’s mission to make travel search more personalized and conversational, Ask AI is an industry first that lets travellers start planning their trip in a chat—while flight, hotel and rental car results update live alongside the conversation, combining the ease of AI with the power of a traditional results page.

Launching just as travel interest ramps up around the World Cup, Ask AI arrives at a time when travelers are planning more complex, multi-city trips. KAYAK data already shows a 12 per cent increase in flight searches to Canadian host cities, including Toronto seeing a 19 per cent increase and Vancouver seeing a 5 per cent increase compared to last summer, with prices and availability expected to shift quickly in the months ahead.

Plan Your Trip with Ask AI
Whether you’re travelling to one match or several, Ask AI helps you move from inspiration to booking in one continuous experience. Search for hotels near a stadium, compare flights between host cities, or build your full itinerary—all without switching tabs.

With Ask AI, travellers can:

• Ask questions using natural language and refine their trip in real time
• Chat while results update live alongside the conversation
• See up-to-date prices and bookable options from hundreds of travel partners

No restarting searches or juggling tabs—just a faster, more intuitive way to plan and book travel.

Tracking World Cup Travel Trends in Real Time

KAYAK is also launching a new dashboard to track how fans are planning trips around the World Cup. Powered by KAYAK’s search and pricing data, it highlights rising travel interest, shifting prices, and the destinations seeing the biggest spikes in interest.

Early trends show:

• Toronto is emerging as Canada’s top host city, with flight searches up 19 per cent year-over-year outpacing Vancouver’s 5 per cent increase 
• Hotel prices are climbing across all host markets: up 55 per cent in Canada, 36 per cent in the U.S., and 119 per cent in Mexico
• Outside of U.S. and Canada interest, Germany and the UK are the regions searching most for travel to Toronto and Vancouver. 

Together, Ask AI and the World Cup Trends Dashboard help travelers plan and compare trips with real-time data, making it easier to make informed decisions as prices and interest change.

Methodology 

Based on flight and hotel searches made on KAYAK in the period between 12.5.2025 and 4.12.2026 for travel between 6.10.2026 and 7.20.2026. They were compared to searches made in the period between 12.5.2024 and 4.12.2025 with the travel period between 6.10.2025 and 7.20.2025. Percentages for changes in searches and pricing are approximate. 

KAYAK, the world’s leading travel search engine, today launched AI Mode, a natural-language search experience that combines KAYAK’s data with ChatGPT to deliver smarter, contextual results, right from the home page. KAYAK is the first major travel site to let users plan complete trips by typing questions directly into a search box.

How to Use AI Mode

• Click the “AI Mode” icon on KAYAK from your desktop or mobile browser to get started.
• Type travel-related questions the way you’d say them to another person.
• Get real-time results as KAYAK compares the latest information and prices from hundreds of travel providers.
• Discover, compare, and book flights, hotels and cars—all in one place.

Travel Demand Heats Up for the Holidays
The debut of KAYAK AI Mode comes at the perfect moment for holiday travel planning, as KAYAK data shows that mid-October through early November is the prime window for scoring the best holiday travel deals.

Prompt your Way to Holiday Savings with KAYAK
To help the AI-curious, KAYAK suggests these festive, holiday-themed prompts to reveal instantly actionable trip ideas – whether it’s a snow-globe-worthy village or a New Year’s Eve bash. Try one in AI Mode or come up with your own to see where it takes you:

• NYC hotels within a half mile of Rockefeller Center for one night, Dec. 23rd
• Cheapest Caribbean destinations for a 7-day trip
• Rent a car from ORD with room for 6 people + lots of Christmas presents and payment at pickup
• Flights from BOS to London for 2 adults, 2 kids, and a baby, Dec. 20 – Dec. 27
• How much would Kevin McCallister’s New York experience cost?
• I want to party for NYE – where should I go?
• You’re in a Hallmark movie. Find me a quintessential winter village for under $600 for flight and hotel.

For tips on writing the best travel prompts, visit KAYAK’s blog.

Today, KAYAK, the world’s leading travel search engine, is dropping a new suite of AI products to help make travel planning decisions faster, easier and more intuitive. These innovations are the result of extensive training of ChatGPT’s AI model on KAYAK’s proprietary database of billions of consumer travel queries. 

At the forefront of today’s release is KAYAK PriceCheck, a new patent-pending price comparison tool. Anyone with KAYAK’s app can upload a screenshot of a flight itinerary from any site, and KAYAK will quickly check hundreds of sites to verify they’re getting a great price.

Also launching today is Ask KAYAK – the company’s latest AI-driven innovation designed to improve and personalize the search experience.  Ask KAYAK lets travelers use simple text entries to search and refine their results. 

Wondering where to go with your family for spring break that’s less than 3 hours from NYC and will cost less than $300 per person? Just Ask KAYAK and you’ll get family-friendly destinations a short-distance away that fit your budget.

Travelers will also see a chat box in the results page where they can input their specific hotel, car or flight requirements. For example, they can enter “United, nonstop, morning departure, <$500” and quickly see their results. Ask KAYAK starts rolling out today and will soon be available to all users in the US, UK and Canada with more markets to follow.

But wait, there’s more. KAYAK is also introducing the following new ways to make travel planning easier:

• Check the scores. Our Provider Quality Scores gives travelers greater confidence when booking a flight by rating providers against a set of quality factors (like price accuracy, customer service, fee transparency and customer satisfaction). Scores are for Online Travel Agencies (OTAs) only.
• Compare ticket options to get what you want. View all of your options even more easily, like what is and what is not included in your flight ticket, when deciding between a basic economy, economy, premium economy or business class ticket for your US domestic flight. 
• KAYAK Trips – now with live updates. With a new simplified itinerary view, KAYAK Trips keeps all your travel plans in one place – no matter where you booked. Now, not only can you build your itinerary through automatic inbox syncing, but you can also get real-time travel updates on your home/lock screens (on iOS).
• Passwords are so 2023. Passkeys are a more secure and user-friendly way to sign in to KAYAK. In fact, since implementing passkeys and ditching passwords, KAYAK reduced the average time it takes users to sign-up and sign-in by 50%. 

There’s a lot of great stuff happening at KAYAK. Learn more about the features announced today HERE. 

After a controlled rollout in April, all ChatGPT Plus subscribers can take advantage of the KAYAK plugin and use AI to power personalized recommendations for travel.

With KAYAK data released last week showing overall flight searches up a whopping 77 per cent in Canada*, this new and more conversational way of planning your next trip becomes a convenient way for Canadians to plan their summer vacation early and expand their chances to find the best flight, hotel and car deals.

Using KAYAK’s plugin is easy, simply type into ChatGPT: “Plan a trip for me from August 1 through August 4 to Orlando, Florida with a $1,500 budget for a family of 2 with a rental car” and voila! Flight, hotel and rental car options are mapped out in seconds and ready to book. 

Methodology

*Flights: KAYAK considered round trip, economy flight searches between 1/1/2023 – 3/31/2023 for travel dates 5/20/2023 – 9/5/2023. For YoY comparison, the same search and travel dates were used in 2022. Prices are in CAD and are on average and subject to change. Destinations were removed based on certain search thresholds and travel advisories in place.

According to a new survey from KAYAK, despite how eager Canadians are to file their taxes (32%) and get their refund sooner, nearly a quarter (24%) have admitted to not spending their tax season on anything fun – and this year can be the year to change that. As Canadians look for the best way to invest their tax refunds, it’s important to remember that there’s no better investment than the one you make on yourself. 

In fact, despite earlier data from KAYAK revealing the growing number of Canadians (27%) eager to take advantage of workcations this year, only 1 in 9 (11%) plan to use their tax return to take a trip or vacation.  

These behaviours differ from our neighbours down south, with KAYAK revealing interesting comparisons between how Canadians and Americans plan to use their tax return*: 

• Half of Canadians (50%) use their tax refund to pay off debt (i.e. credit cards, loans, bills) compared to 41 per cent of Americans 
• More Americans have used their tax refund in past to take a trip (16%) compared to only 9 per cent of Canadians
• 1 in 6 Americans who expect to get money back for their 2021 returns are enthusiastically planning to spend it on travel, compared to only 1 in 9 Canadians

Canadians on a tight budget shouldn’t rule out the possibility of investing in themselves this summer. For those looking to escape and make the most of the season (and their tax return), KAYAK has compiled a list of the most affordable roundtrip destinations for Canadians by city to help take their next trip without breaking the bank**:

To help Canadians looking to splurge on their wanderlust, KAYAK also launched an interactive tax refund calculator to show the ways that Canadians can consider reinvesting in themselves this year. I’d be happy to put you in touch with a KAYAK spokesperson who can discuss these tax return trends and speak to how Canadians can best use their tax refunds to plan their next trip.

*YouGov Methodology:

This survey has been conducted using an online interview administered to members of the YouGov Plc panel of individuals who have agreed to take part in surveys. All figures, unless otherwise stated, are from YouGov Plc. Canadian survey: Total sample size was 1005 adults. Fieldwork was undertaken between 4th – 14th March 2022. The survey was carried out online. The figures have been weighted and are representative of all Canadian adults (aged 18+); U.S. survey: Total sample size was 1084 adults. Fieldwork was undertaken between 16th – 17th February 2022.  The survey was carried out online. The figures have been weighted and are representative of all US adults (aged 18+).

**Methodology: KAYAK considered searches originating in Canada for international travel from 5.27.22 through 9.5.22 (all prices listed are in USD).

According to a new survey from KAYAK, more than one quarter (27 per cent) of employed Canadians plan to take a workcation (i.e. working remotely from a different location) in 2022. This trend is even more prominent amongst Gen Z’s (aged 18-24), with 38 per cent planning to take a workcation this year. To capture this growing demand for blending the flexibility of remote work with leisure travel, KAYAK is launching an interactive “Work from Wherever” Guide to help those interested in taking a workcation find the best place to go based on their personal style.

Who needs a workcation

According to the survey, one quarter (25 per cent) of employed Canadians feel burned out from their current job and the same amount (25 per cent) have fantasized about quitting their jobs. To support those looking for a change of scenery to reignite their day-to-day motivation, KAYAK’s new tool is here to help. 

Featuring data-driven insights on the most popular destinations to work remotely, KAYAK’s “Work from Wherever” Guide aims to help personalize where to workcation in 2022. From the average price of a flight, hotel and rental car to the internet speed and compatible timezones, KAYAK took a number of factors into account to determine the best place to workcation based on Canadians’ personal and professional needs.

The guide also features a sweepstakes where one lucky winner will receive two, Economy, round-trip Air Canada flight tickets for anywhere the airline flies, plus $7,400 in gift cards to put toward their own workcation.

Where to workcation 

From European favourites like Lisbon (Portugal) and Barcelona (Spain) to Central American hotspots like Santa Teresa (Costa Rica) and Bocas Del Toro (Panama), metropolitan cities with nearby beach escapes (for quick weekend trips) are where Canadians are searching to travel in 2022.

Whether you’re considering a workcation now or in the future, KAYAK has additional tools to help you plan your trip confidently. Check out KAYAK’s Travel Restrictions Page which provides country level details on vaccination rates as well as KAYAK’s recent partnership with CLEAR offering an easy way to show proof of vaccination before traveling internationally.

** Remote employees should check with their employers for any immigration, tax considerations, etc. when debating whether to work remotely from another destination **