Thankfully, the days of assembling heavy space-hungry plastic envelopes filled with printed confirmations of all bookings and associated documentation are long gone. This is thanks in part to itinerary management apps capable of organizing fragmented bookings into an organized electronic package. I’ve used five different itinerary apps from time to time and on three trips in 2014 conducted a comparison test of three popular creations – Kayak, TripIt and WorldMate. Kayak “My Trips” consistently emerged head and shoulders above the rest as my favourite itinerary management app.

How an itinerary management app works

Essentially, booking confirmations are forwarded via email to an itinerary management website’s dedicated email address (e.g., or In the case of TripIt, a user can choose to activate the auto-import feature that scans an email account for travel confirmations on a regular basis. The bookings are then organized and categorized into separate trips and displayed in an attractive readily accessible format. All details can be readily edited or notes added by accessing the user’s online account. The beauty of this kind of travel app is that all itinerary details are stored in one place within easy reach on a mobile device.

Kayak accurately processes all bookings

The major strength of “My Trips” is that there isn’t a booking Kayak can’t process. Once I forward bookings to, I can rest assured Kayak will get them right, and correctly merge them into the right trip. This is a major time saver, and where Kayak has the edge over the more popular TripIt and WorldMate. There’s never a need to figure out how to resend a booking in a different format and I rarely have to spend time editing what Kayak has processed.

Past trips remain in an itinerary management app

A major disadvantage of TripIt and WorldMate is that they only seem to be able to recognize “supported booking vendors” or “supported providers.” As such, these apps may be useful to business travellers who customarily fly with major carriers, reserve vehicles at easily recognizable car rental agencies or book accommodation at brand-name hotels. However, for those who stay in hostels or family-owned guesthouses, book independent tours or use a variety of transportation options, Kayak is a much better choice.

For example, if I plan to stay in private accommodation, I will draft a very short email with the name, address and telephone number of my host and send it to Kayak. This is sufficient for Kayak to add this “booking” to my itinerary. WorldMate can’t process this kind of email as it didn’t originate from a “supported provider” and therefore, it needs to be manually entered. TripIt will add it as a Note in Unfiled Items. The same holds true for hostel bookings. Kayak inserted my booking at Planet Traveler in Toronto correctly, WorldMate couldn’t process it at all and TripIt added the email (but not the attachment with the booking details) as a Note.

A RocketMiles booking of a brand-name hotel was processed by both Kayak and WorldMate but TripIt was only capable of adding a Note. Surprisingly, an Expedia booking of an apartment in Amsterdam could not be processed by WorldMate, and a bike-and-barge tour in the Netherlands could only be processed by Kayak. Similarly, the “Love Letter Train Tour” by the Mural Arts Program in Philadelphia could only be processed by Kayak.

TripIt also doesn’t fare well when it comes to selecting an accurate name for a trip. For example, I sent my Aeroplan itinerary for a trip to Taiwan to all three sites. Kayak and WorldMate both selected “Taipei Trip” for the name of the trip whereas TripIt chose “Toronto Trip.” Toronto is the first of three stops on the way to Taipei.

Unfortunately, the poor performances of Tripit and WorldMate render these apps useless for my purposes.

User-friendly interface

Kayak’s user interface is simple and efficient, especially on the iPad app. Each trip is presented as a clean looking short scrollable list with each booking displayed with its date, a descriptive icon (e.g., plane, train, bed or car) and a short description of each activity. Beside an icon of an airport runway is the layover time between flights.

Itinerary displayed in itinerary management app

Tapping on a booking reveals further information including a map, departure and arrival information and booking details. A “taxi view” of each accommodation booking displays the name and address in large print to show to a taxi driver or helpful local.

Taxi view in Kayak itinerary app

Calendar synchronization

In the Trips Settings, Kayak provides helpful instructions on how to establish a feed with a traveller’s calendar. Within a couple of minutes, the Calendar app on both my iPad and iPhone is fully populated with all my bookings and key details. For example, with the contact information associated with an apartment booking included, I can visit the website to confirm amenities or contact the host on arrival – all from within the Calendar or Kayak apps.

Email alerts

Kayak’s email alert feature is very efficient. The 24-hour check-in alert is a timely reminder to check in, select a seat (or confirm seat selection) and obtain a boarding pass. It provides a very handy direct link to the airline’s web check-in page to do so.

Kayak 24-hour check in email

The flight delay alert not only keeps me updated on possible flight delays, but the email notification includes helpful information. For example, prior to leaving my Dead Sea hotel for the 45-minute drive to the airport in Amman, I had several hours’ notice of an expected delay of my flight to Istanbul. The email contained my flight number, booking confirmation number, revised flight details and the contact telephone number for Royal Jordanian Airlines that I could call from within the email. To obtain this service with TripIt, I would need to upgrade to TripIt Pro that comes with an annual fee of $49.

Another convenient feature is the email alert advising me of terminal and gate numbers (including changes) of connecting flights. Before disembarking, I know where I’m headed, which is especially useful with tight connecting times. Again, this service with TripIt would require an upgrade to TripIt Pro.

Kayak gate change emailSharing with others

“My Trips” allows me to automatically share any new trips with a designated person or people. When sharing my itinerary with others, I can keep parts of my trip private. This feature is especially useful when planning a trip with travel mates, or when visiting someone who could benefit from knowing my travel plans.

Booking documentation

A fantastic feature I really appreciate is Kayak’s ability to save the original email and attachment of each booking. With Kayak, I always have a digital copy of the documentation confirming the booking. This is especially useful when I need to reacquaint myself with details of a booking, or for verification purposes when communicating with the service provider. While I keep copies of these bookings in my email system and Dropbox folder, it’s a helpful timesaver to be able to quickly access them from within the itinerary management app.

Kayak includes original booking confirmation in itinerary app

Features of Kayak app on iPhoneAnd there’s more…

“My Trips” is not the only feature of the Kayak app. The app has the capacity to make bookings for hotels, flights and cars and I appreciate that these are separate from my itinerary. I can activate the Flight Tracker feature to see if my flight is on time or enable Price Alerts to be notified when prices change. Airline baggage fees, packing lists and a currency converter are additional features. The app also supports Passbook for storing boarding passes.

Using Kayak “My Trips”

Some travellers like the auto-import feature of TripIt. I found it to be both a blessing and a curse and eventually disabled it. How it works is that TripIt scans an email inbox several times a day and automatically populates an account with any bookings it finds. This might be desirable for work-related travel but in my case, it added to my workload for a couple of different reasons. One is that I often book travel many months in advance and during the period leading up to the trip, flight times or seat assignments invariably change. The result was that amended versions of the original itinerary were sent to my inbox and a conflicting version added to my itinerary. This would require an intervention on my part to delete the incorrect one.

In addition, I often travel with other people who would send me their itineraries and related bookings. TripIt recognized all of these emails as travel plans and populated my account with multiple versions of different bookings. Having to manually edit what TripIt had posted was labour intensive and convinced me that I prefer a system where I can manually forward each booking, and to do so a few days before each trip.

With all emails stored in a trip-specific folder in my email account, and all attachments saved to a trip-specific folder on my computer, my role in setting up an itinerary is simply a matter of forwarding emails from my email address to and then verifying the accuracy of the bookings at the Kayak site.

Kayak packs a huge punch for a free app. For those who prefer an ad-free experience for 99 cents, Kayak PRO includes airport terminal maps as an added feature.

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