One of the blogs I follow (Thread Tripping) recently had a post about different itinerary managers.  These managers offer a convenient place to keep all of your reservation information and dates.  I had no idea there were options other than Tripit so I signed up for all of them and gave them a try.  I imported my next three trips: a weekend in San Diego, my Honeymoon, and a ski trip to Utah.  It included a variety of air and hotel types including a Southwest booking for two people on points, which turned out to be the most difficult to import because of the way Southwest generates two confirmation numbers for one email.  Here are my thoughts and the one I’m going to be using going forward.

UPDATE: 2/21/17:  This post has become pretty popular since I put it up a year ago so I took the top two (TripIt and Kayak My Trips) and have done an updated and more in-depth comparison which you can read about here:  TripIt vs. Kayak My Trips.

Lets start by discussing some features that all of these sites share.  The biggest is that you simply forward a confirmation email to them and they automatically parse the email for the information and add it to your account.  They all also have the ability to manually add data but I can’t see how that would ever be useful if the email thing works.  It is worth noting that this email parsing is extremely complicated since it needs to be able to work with any email over thousands of companies; unfortunately, it doesn’t always work.  They also all have the ability to merge multiple trips together which is useful if you first send it the flight there and then the flight back with nothing in between and it assumes you have two trips.  Each of them has an app available for Android and iOS, which makes it much easier to use on the road.  Finally, they also all have the ability to share your itinerary with others which is both nice and expected at this point.

TripIt

We should start with TripIt since it’s the most widely known one and gets recommend a lot.  TripIt correctly added everything I sent at it.  When emails included multiple travelers it handled it perfectly including multiple loyalty numbers, confirmation numbers, and ticket numbers.  Unfortunately, it doesn’t handle layovers as well as I’d like and often split a simple one stop flight into two flights and makes the layover info harder to find.  it correctly finds the aircraft type but doesn’t include terminal information.  For hotels, it correctly found the loyalty number, confirmation number, and room type.  My biggest gripe with TripIt is that it often orders things in a weird way.  If you are flying into a city and then staying in the hotel there, it will often order it as hotel then flight or sometimes flight then hotel then flight.  if you’re checking out of one hotel and into another, it will sometimes mix these up as well.  Thankfully you can manually edit the times for these which usually fixes the order, but shouldn’t be necessary.  Tripit has some cool collaboration features (when they work) that make it easy for multiple people to add to a trip together or just add viewers to the trip that can’t edit.  It also allows you to connect with other TripIt users and see their plans.  Kinda creepy but I’ve found it useful a couple times and they make it easy to understand how to make a trip private.  TripIt doesn’t handle automatically adding things like tours and events very well and mostly works on Hotels, Flights, and Cars; though you can always manually edit them.  My final complaint is that TripIt is just ugly.  It has lots of ads on the side (often very colorful and moving) and has tons of wasted white space in the middle of the information.  It also wastes a lot of space trying to give you directions and weather info between each event.  Honestly TripIt, I have apps for travel and weather already so I’m not going to be using yours.  You can delete the travel but not the weather if you want to clean things up.  They also seem to want to sell you other services for TripIt pro but I don’t find it worth the extra money.

Pros:

Handles multiple travelers well
Good Collaboration Features

Cons:

Ugly – moving ads and wasted space
Doesn’t get terminal info
Weird ordering of events

WorldMate

WorldMate correctly read in all of the reservations I sent at it and made the trips as you would expect.  Based on the buttons at the top of a trip, WorldMate seems to mostly work for Flights, Hotels, Car Rentals, Public Transportation, and Meetings.  It doesn’t offer an easy way to add other things like tours.  For flights, it has a checkin button to make it easier to checkin before a flight, but I couldn’t test this since I don’t have a flight for a few weeks.  For the hotels I imported, it didn’t include the loyalty number, the room type, or the confirmation number.  However, on the flights, it did include the terminal info, ticket number, confirmation number,  price, and aircraft type.  The negative here was that it didn’t include layover info and only included the ticket number and confirmation number for one of the people flying not both.  We were given two different confirmation numbers for one of the flights since it was an award ticket on Southwest and it only put in the info for mine.  On trips when we had only one confirmation but two ticket numbers, it still only included mine.  The share feature can share your itinerary over email with somebody but lacks any kind of collaboration.  You can add your linked-in information and it will tell you when you are traveling near somebody you’re connected with that also uses WorldMate.  I’d rather have Facebook integration personally but want the ability to choose who I share my travel info with.  This gets into the creepy and dangerous category if you aren’t careful.  This also assumes they use WorldMate and since it gets the least attention of these four, chances aren’t good.  My final though on WorldMate is that it is just ugly and full of ads.  It looks more like they want to advertise and convince you to buy a flight from them than it does provide a good experience.  The sad thing is that it still looks better than TripIt.

Pros:

Gets terminal info and aircraft type
Button for easy check-in

Cons:

Limited event types
No Collaboration
Didn’t get all ticket and confirmation numbers
Ugly with lots of ads

TripCase

TripCase is another one that gets recommended a lot, probably because it is built by Sabre and many workplaces use it.  When moving from TripIt to TripCase the first thing I noticed was how much cleaner it was.  It doesn’t have all the adds on the side, except for it’s own stuff, and is a much better use of space.  I like how it has the most needed info available at a glance but you can click details to get more info.  It does this much better than TripIt and WorldMate.  I also like that you can manually add directions or weather between events, it doesn’t auto add them.  However, TripCase failed to import a Southwest flight, probably because it contained two travelers with two different confirmation numbers.  It also failed to retrieve a lot of info from the hotel: no confirmation number, loyalty number, or room type.  When it did pull in a flight, it didn’t get the ticket numbers or the loyalty numbers.  TripCase has no collaboration features though it does allow you to share your itinerary.  It didn’t get the terminal info for our flights or even suggest there was a layover but did get the aircraft type.  TripCase also gets lots of complaints about not handling cruises well, if that is something that matters to you.

Pros:

Looks nice and clean
May be good for companies using Sabre

Cons:

Doesn’t always work
Doesn’t include useful info

Kayak myTrips

Kayak auto imported everything perfectly, even the tricky ones.  It handled the multiple traveller/confirmation numbers almost as well as TripIt though in a slightly different way.  I think for this very tricky ticket I like the way TripIt showed it, but for every other flight I’ve put in, Kayak is better.  it correctly got all of the ticket numbers, confirmation numbers, and loyalty numbers.  Unfortunately, Kayak doesn’t include information about terminal and gate numbers or aircraft type.  However, it does show the layover time well and include links to maps of the terminals, which was unique.  It correctly found all of the information about the hotels such as room type, number of guests, confirmation number but didn’t include the loyalty number.  Kayak is almost as pretty as TripCase but is just as clean and doesn’t include ads.  It works well for adding in unique events like tours and scuba trips.  It also has good collaboration tools to allow others to view or edit the trip.

Pros:

Very clean and readable
No ads
Worked best for importing
Good collaboration tools
Terminal Maps

Cons:

Doesn’t give hotel loyalty numbers
Doesn’t show terminal or gate info
Doesn’t have aircraft type

Conclusion:

From now on, I’ll be using Kayak.  Kayak and TripIt were the only ones that have the features I want and work all the time.  Of those, Kayak looks a lot better and I like the way it organizes data better.  I wish it included a couple more things but I can live without those in exchange for working all the time.

What do you think?  Do you have a favorite not listed here or think I missed the mark completely?  Leave a comment below and call me out on it, I’m always looking for the best products.

UPDATE: 2/21/17:  THIS POST IS OUT OF DATE.  Since writing this almost a year ago, Kayak and Tripit have been updated.  You can read a new comparison of those two on the new post here:  TripIt vs. Kayak My Trips.

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