New Kayak Best Time To Book Tool (2023)

How To Use Kayak Best Time To Travel Tool (2023)

Can Kayak Best Time To Travel help you save money and make the best decisions when you plan a trip? Let’s find out! Last week I wrote about Skyscanner Savings Generator, a beta tool allowing users to get insights from historical data. Now Kayak has come up with its competitor but implemented it much better.

Kayak has been losing terrain against Hopper (launched in 2007), a digital travel agency with AI-powered price watches and notification tools. A significant portion of Hopper’s growth can be attributed to its innovative flight prediction capabilities, which tell you when to travel and when to book.

Kayak Best Time To Travel Tutorial

Know when to book your next trip.

That’s how Kayak advertises the new tool. To start using the tool, you need to input your home airport, final destination, and trip duration (so far, there are only a few pre-defined lengths). The tool recommends the most optimal month for the trip based on various factors such as cost, crowd density, and weather.

Once you select your preferred travel month, the tool proposes more precise periods within that month and even provides a detailed analysis of average, minimum, and maximum flight prices for every month throughout the year! That is very cool; see my examples below.

How to use the new Kayak Best Time To Travel Tool (Tutorial)

1. Enter your Origin and Destination

Use the two fields on the landing page to enter your home and destination airport. Note that the tool is only working for round trips so far. In my case, I tested out from Stockholm to New York.

Kayak Best Time To Travel Tutorial 3

2. Select your trip duration and hit Search

From the dropdown menu, select if it is a 4, 7, or 14-day trip. According to Kayak, these pre-defined lengths are what people are most used to and what moves a significant volume of searches.

Kayak Best Time To Travel Tutorial 2

3. Find out which month to go.

Kayak’s tool will recommend the best month to go to your destination and why. Typically it’s due to lower airfare, decent weather, and better hotel prices.

In my case, the recommended month was October.

Kayak Best Time To Travel Tutorial 4

Below is more information about the average flight, hotel prices, and weather. Interestingly, flight prices were cheaper in September in my New York example, but the whole combo was cheaper in October.

Kayak Best Time To Travel Tutorial 5

When you click on the boxes, you get even more information about the average prices and how they change over time.

Kayak Best Time To Travel Tutorial - Average flight prices.
Kayak Best Time To Travel Estimated Flight Prices

They also display weather information per month, which is good to have at hand when planning.

Kayak Best Time To Travel Tutorial - Weather information
Kayak Best Time To Travel – Weather information

4. Narrow down your dates.

Scrolling a bit more, Kayak shows suggestions on exact dates for when to book flights. In my case, it suggested booking from October 6th to 9th.

Kayak Best Time To Travel Tutorial - Nail down your dates.

Then, it will also display a timeline with all potential options and the price differences. You can directly search for flights on Kayak.

Kayak Best Time To Travel Tutorial - Flight prices over time.

5. Understand when to book.

Once you’ve found your potential travel dates and itinerary, Kayak also gives advice on exactly when you need to book (how far in advance). Understanding when to book is really important and one of the most common questions from travelers. Should I book now or wait for a sale? What if prices go down?

The innovative part of Hopper, when it was launched, was that it was the very first tool that advised on when to book flights based on real data. It also gave users a benchmark of average prices, and it was really clear to understand if you were booking a cheap or expensive ticket. With time, other tools added this benchmark, such as Kayak, Google Flights, Expedia, and

In my example, Kayak says I should book the flight by August. It also offers me to set up price alerts to monitor changes.

Kayak Best Time To Travel Tutorial - Understand when to book.


That’s pretty much it. When ready, you can start finding hotels and flights using Kayak’s metasearch.


One aspect I like is that Kayak is being very upfront about the kind of data they use and how the process it. As a data scientist, this is very much appreciated.

Kayak’s recommendation on which month to travel is calculated based on the presented four factors: average flight prices, popularity, average temperature, and average precipitation. Flight prices, popularity, and precipitation constitute inverse factors; the less, the better. Average temperature optimal values are taken as the median for the destination, and a difference is calculated for each month from this reference point. The smaller the difference, the higher the month moves in the recommendation. Flight prices and temperature factors are weighed double as much as popularity and precipitation. December is excluded due to ambiguous prices and popularity patterns around Christmas travel. In case of unavailable data for any of the aforementioned factors, the recommendation is estimated based on the rest of the available factors.

The best time to book insights are estimated from Kayak’s internal historical search data. Search data from the past year is aggregated for each day difference between the date of departure and search date from 0 to 183 days (about 6 months ahead is the earliest we consider), taking the bottom 10 percentile of hotel prices and flight prices of economy class. The minimum prices and corresponding day difference is identified to approximate the best times to book flight tickets for the specific route and hotels for the specific destination city. The underlying dataset is updated weekly. In case of missing insights, the route or destination city in question have less than 40 data points per day difference.

Prices are estimates based on an analysis of current and historical minimum roundtrip prices for one traveler. Prices include monthly averages and the greatest and least percentages in intervals of ten for each trip length. With this data, they try to forecast future minimum price trends – these estimates are subject to change and should be interpreted as a rough directional guide.

Kayak ChatGPT Plugin

Recently, Kayak joined hands with OpenAI to launch a plugin that assists ChatGPT users in completing bookings for travel itineraries suggested by the chatbot. I tried this plugin, read more about it here.

The first implementation still sucks because it fails at solving complex queries. Still, it is a good start and opens up for really great innovation


I’ve been in love with Kayak since the first time I used it, and I have been consistently using the app to arrange my trips, track flights, and even monitor price changes. I remember that Kayak was one of the first apps to support the Apple Watch and has always been striving for innovation.

The Best Time to Travel tool is a great addition. When you are planning a vacation, there’s usually a lot of information missing about your destination(s). You can search for landmarks, places to eat, and recommendations, but you are missing the market data. That’s why finding the perfect time for booking is so hard.

Kayak solves this problem by digesting and sharing their own data. They have pre-processed millions of data points and summarized them beautifully and intuitively. While it might not fit everyone’s plans, they have covered much of the curve with the most common use cases and searches.

Overall, a great initiative from Kayak, bringing the power of data closer to the users, helping them make more informed decisions.

What’s your experience? Let me know in the comments below.

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