Almost a year ago I wrote the post The Best Travel Itinerary Manager and it quickly became my most popular post. In that post I gave my preference for Kayak over the established TripIt for managing itineraries. Since then I’ve used them much more and they’ve both had updates so I thought it might be a good idea to review them again in a little more depth. I’m covering TripIt since it is the entrenched favorite and Kayak My Trips because it is second place in google searches and is my favorite.Lets start by discussing the features both of these programs share. The most important feature is that you simply forward the confirmation email from your hotel or flight to them and it automatically imports it. You can also manually add data, edit data if it is wrong, and merge trips together when they inevitably create separate trips from two one-way flights. They both have apps for iOS and Android that work pretty well. They both have collaboration features that allow you to work with others or share your trip. They both have calendar subscription feature so that you can get your travel in your calendar app on any platform (works perfectly on my iCal app on iOS). They both show the cost of each item in your trip (but only if the email included it). Now, lets look at some of the differences.
Kayak My Trips
Kayak’s has a calendar feature that is actually two calendars – one that is for all your trips and one that doesn’t include any of the trips you’ve marked private. So you could use the first link and then give your boss the second link and he would only have your flight info for business trips, not personal trips.
Kayak also has a link for each flight to the fees for the carrier. This is a nice way to quickly check baggage fees or cancelation fees without searching online. Not really all that useful but doesn’t hurt anything and might be useful every once in awhile.
Kayak has the ability to turn on or off alerts for a specific itinerary. This might be useful if a flight time is constantly being changed by five minutes and you’re tired of getting the alerts (I’m looking at you Delta). But this does highlight that they have trip alerts (available as app notifications, emails, or SMS messages) and TripIt doesn’t unless you pay for the pro version.
Kayak has links to terminal maps next to each of the cities in a flight. And they’re actually really good maps – probably the best implementation I’ve ever seen, certainly better than most airline apps. These are also available in the mobile app, which is great since I never seem to look until the plane is landing.
Kayak makes it really easy to add notes to any travel item. Just click edit and start typing then click save. No page reload required. On TripIt, you have to edit the travel item, then scroll down to “notes” on the next page, then save. And this gives you the ability to accidentally edit one of the important travel details, which is bad. I use this most often when I have a booking reference number from the airline I booked with but also have another with the airline the flight is on that I need to choose seats.
The Kayak app for iOS (and I’m assuming it’s the same for Android) has a button for every item with an address (attractions, events, and hotels) that says taxi view. You can click this and it puts the address full screen on the phone screen. This is great if you need to quickly show the taxi driver where it is, especially you don’t speak the local language. But remember, this only works if the reservation confirmation included an address or you added one yourself. Otherwise it just puts the hotel name and your name on the screen.
Kayak also has one of the best collaborating features I’ve seen. You can add the email address of another Kayak user and share trips with them (and even allow them to edit your trips). That’s not special though, pretty much all itinerary managers do that, including TripIt. The cool part here is that you can also input multiple email addresses to associate with your account. For me that means I put my wife’s email address in there with mine so that whenever Kayak gets an email from either of those email addresses, it puts them in my account. We don’t want to manage a separate account for her and this is easier than her forwarding everything to me to then forward to Kayak. This is a really simple feature but it ends up making life so much easier for households with two travelers but only one planner.
Kayak has check-in reminders for flights so a couple of minutes before 24 hours before a flight, you get an email and an app notification (not sms) to check in. This is important on airlines like Southwest where check-in time determines boarding or on some airlines where check-in time matters for upgrade priority. It’s also useful for other airlines since many frequent flyers get upgraded at the 24 hour mark and you can look at the seat map and perhaps get a better seat. After the 24 hour mark, both Kayak and TripIt have links on the itinerary to check in for the flight and TripIt has a link to get flight status from Flightstats.com. TripIt gets the edge for checkin links but it loses because it doesn’t give you the reminder.
And the biggest feature for Kayak is that you can click a link to view the original email that you sent them for any travel item. This is super useful if Kayak missed something (which they both did fairly frequently) or you need to pull it up to show it to a hotel clerk, etc. I use this feature a lot and I love it. The only negative is that if you send multiple emails for the same item, it only saves the last email.
TripIt
TripIt has a feature to Automatically forward plans. You link an email account and it automatically searches that email account a few times a day and pulls in all your reservations. Personally I find that creepy and I don’t trust them so I don’t use it. Plus, it doesn’t always work they way I want when I sometimes receive multiple confirmations or confirmations I don’t want to include (eg: if I buy a ticket for my mom and have the confirmation emailed to me).
TripIt has stats on your travel for both the current year and all time. I find this pretty useless since I already use FlightDiary.net (discussed in detail here), which gives better stats. But it doesn’t hurt and some people might like it.
TripIt also has social media integration. You can publish your trip to Facebook, LinkedIn, Yammer, or Salesforce and your friends will see the basics of your trip. Again, I don’s use this because I don’t trust them to 1) not steal my data, 2) not have my information stolen from them if TripIt gets hacked, and 3) not accidentally publish data I don’t want published if there is a software error. Besides, it’s usually not a good idea to tell everybody when you’re going on vacation. And when I want to, I can just write the post myself, thank you very much.
TripIt does have some cool network stuff of it’s own though. If you have friends or co-workers using TripIt you can add them to your network and you can see any travel they have public. This is cool when you see a friend will be traveling to Chicago and you recommend a nice pizza place. Or when you realize you’ll be in DC at the same time as somebody and you can plan to get dinner. But I could see it getting real weird to have people following your travels and even weirder if you forget to make something private.
TripIt also has a comments feature that I really liked. You can quickly add comments to the trip using a box near the bottom of the trip below all the ads. This is really only useful if you want to have a conversation with the people you’re sharing the trip with. Maybe links to potential hotels or attractions or restaurants you want to try.
TripIt is the only one of these two apps that has a smartwatch application. (I believe TripCase also has one – for what it’s worth). I don’t care about this and most people seem to not care about this. You need to have your phone with you anyway to use most watches and it has a bigger screen. Plus, I probably will be using the airlines app on the watch so I don’t see what advantage the TripIt watch app would have. But I could be wrong since I don’t have a smartwatch.
TripIt offers seat advice for each of the flights through seatexpert.com. However, I tried it with almost all of these flights and it never worked. It would just think for a long time then take me to a screen with a list of all the planes that airline operates and I have to chose the plane type and version. It might be cool if they ever fix this. Instead, I just go to seatguru.com and type in the airline, flight number, and date and it actually works.
The coolest thing TripIt does is look up the plane type of the flights as well as the distance in miles. Both of these things are pretty easy to do but Kayak doesn’t do them and I find myself missing it every time. I do wish it had on time percentages; it has the space for the data, it just never filled it in for me.
And finally let’s talk about TripIt Pro. There’s a 30 day free trial and then it’s $59 a year unless you get it for free with your credit card (I had it free for a year from the Barclay Arrival Plus card, which has since discontinued it). With TripIt Pro you get a bunch of additional features including seat monitoring (see above for seat advice), fare monitoring (only useful if you get free cancelations), alternate flights (useful for cancelations but doesn’t work as well as you’d hope), and trip notifications. Most of that stuff is dumb and I wouldn’t use them. But the notifications are really important and it’s annoying you have to pay to get them when you don’t with Kayak. I realize that’s how capitalism works but they already show so many ads, also being asked to pay is too much for me. I guess Kayak is just hoping that the My Trips service drives you to use them – and I think it does. What I need to search for a flight and I have a choice between Expedia, Orbitz, and Kayak, Kayak is what I go to because I’m so used to it. TripIt Pro also has a feature to track your miles and points balances but I use awardwallet already and I hear it’s better than TripIt.
The Test
I’ve been using these two apps for the last year. But to put them to the test, I deleted everything and uploaded my next four trips. A couple of these are simple but the other two are quite complicated trips for multiple people, often flying one airline while using another airline’s miles.
- A ski trip to Utah that’s relatively simple flying Southwest there and Delta back and staying at one hotel.
- A complicated trip to Toulouse involving 8 airlines and 7 hotels. A one way flight to Chicago on Southwest and a night there. Then a Virgin Atlantic flight to London staying a night. Then a British Airways flight to Bordeaux and a few nights there. Then a few nights in Toulouse. Then my wife is flying back on United and Lufthansa and I’m staying a few nights in Marseilles then flying home on Iberia and American staying a night in Madrid.
- A quick weekend trip to San Diego for my wife, myself, my mom, and my grandma to see my sister get married. It’s there and back on Southwest, two reservations at a single hotel, and a car rental.
- A complicated trip to Angor Wat. Flying American and Cathay Pacific to Hong Kong for a couple nights. Then a flight to Siem Reap on Dragonair and four nights there. Then a flight to Phuket on Bangkok Airways for five nights. Then a flight to Hong Kong on Air Asia and a flight home on Cathay Pacific, Japan Airlines, and American.
Overall, they did both better and worse than I expected. The fact that computers can analyze these documents and piece them together at all is still kind of amazing. Both of them updated within seconds of me sending the email, and they were almost always right. But there were a few times where they failed or had weird ideas about how to display things.
Notifications
Lets talk about notifications first. Over the last year I took many trips that had notification worthy events. Some were just airplane changes many months out but some were large time changes or cancelations. In most cases I received notifications from four services: The airline, Kayak, TripIt, and Awardwallet, which automatically gathers some flights. There was absolutely no rhyme or reason to the order the notifications came in. Sometimes TripIt was first and sometimes it was last by several days. Same for Kayak. In a few cases the airline was the first to alert me so having all of these other services didn’t help one lick. Overall, I found that Awardwallet was the best at alerting me to plane type changes, which Kayak and TripIt often missed. But for the most important notification – that a flight was cancelled leaving for vacation – the first notification wasn’t any of these services. It was my grandmother checking on our flight the day before and happened to notice it was canceled. So I guess the best advice here is to use multiple services and hope they work but don’t count on any of them.
Confirmation Number or Flight Number
After importing all of these flights, I finally think I understand how the two programs sort things. Kayak combines things that have the same confirmation number. For our delta flight SLC-OKC, we sent in two different emails (one for each passenger) but since they had the same confirmation number, Kayak combined it into one travel event. For our Southwest flight OKC-MDW we used points so Southwest automatically generates a separate confirmation number for each person. So we have two travel events even though we’re on the same flight. And for our Southwest flight to San Diego and back, we have three different confirmation numbers (Wife and Me on one paid, grandma on one with points, and mom on one with points) so Kayak shows three different travel events. I can only imagine how intense that would be with a bigger family using all points.
TripIt, on the other hand, combines things by flight number – sometimes. If you send it the emails, it will combine by flight number, but if you manually input the details, it will combine based on confirmation number like Kayak. For that Delta flight SCL-OKC it correctly generated one travel event because they had the same flight number and date. For the OKC-MDW flight, it also combined them into one travel event because they were the same flight and it shows two confirmation numbers (no way to sort out which confirmation number is for who though). And again for the flight to San Diego, it made a single travel event because it saw that it was the same flight.
Winner: Tie
I definitely like the way it looks when TripIt combines based on flight rather than confirmation. However, there’s no distinguishing the confirmation number if you need to call the airline or check the flight online. Plus, the online check-in button doesn’t work because it tries to auto fill in both confirmation numbers. Also, TripIt fails completely if you have two segments with the same flight number. This happens most often on Southwest but can happen on other carriers too. Our flights TUL-LAS-SAN where both flight WN5668. Kayak showed it correctly but TripIt showed it as a non-stop with no layover.
Event Order
The biggest complaint I had about TripIt last time I did a review was that it would incorrectly order events. If the check-in time for a Chicago hotel was 12pm, it would put it before a flight at 3pm going OKC-Chicago. At first glance this seems logical because one time is before the other. But this isn’t how you want to use it on the road. It makes more sense to order things in the event they should happen, which in this case would be flight then hotel. The good new is that they got this fixed and everything now shows as it should. I don’t know how they fixed it, but I can’t find an instance where it doesn’t work so there must be some intense if-else statements in there somewhere.
Winner: Tie
Design
Here is where we get to the big difference between the two services. Kayak has one small add at the very bottom for car rental. TripIt has lots of big bright ads, which are weirdly enough all about TripIt Pro. It’s almost more insulting that they are all ads for TripIt Pro. If they were ads TripIt was making money on, I could justify it as them recuperating the cost of offering this service. But it’s just the same ads for a service I already know about and choose not to use, which is also advertised in other ways on the site. So at that point it’s more about annoying me trying to gain additional money.
My next complaint about the user interface is the map. When you click on an address in TripIt, it opens a new TripIt page with a very small Google Map. Kayak on the other hand opens the map in Google Maps, which can be full screen and do all the other cool things that Google Maps can do like street view, satellite view, and directions.
Below is an example from an upcoming trip showing just the first two events, a flight and a hotel. Even with Southwest taking up twice as much space because of confirmation numbers, it still takes up less than half the length that TripIt does. And even if you delete the driving directions to the hotel (that still appear before the flight!) and TripIt were to get rid of the Rome2Rio transportation, there would still be a ton of wasted space because they’ve chosen a very inefficient layout. I don’t want to squeeze everything too much, but the more I can see on one screen, the better.
TripIt also just has a “clunky” user interface. With Kayak, you see the important details and if you want to see everything you click Show Details and all the information is there. It takes up about twice as much space but only shows the information it has rather than wasting space for details it doesn’t have. With TripIt, there are seven different drop downs to see more information. And when you open those drop downs, most of that space is empty space because it doesn’t have those details.
Winner: Kayak My Trips. Hands down, no contest.
Conclusion
You can’t really go wrong with either of these and the differences between them seem small compared to their similarities. From now on, I’ll be using Kayak My Trips. Overall, I find the features from Kayak more useful than the ones from TripIt, but that’s just my opinion based on how I use the products and you are sure to differ. Ultimately, it comes down to the fact that Kayak looks cleaner, has less wasted space, and has fewer ads. On the off chance that somebody from Kayak or TripIt reads this, here is some advice for how to improve:
How to improve Kayak myTrips
- Don’t show two events for the same flight, even if there are different confirmation numbers. Instead, move the confirmation number down with the passenger info like ticket number.
- I’d really love to have the flight distance. There are a lot of places online that have this so it can’t be too hard.
- And finally, the airline nerd in me would love to have plane type. Maybe partner with SeatGuru.com and they could provide not only the aircraft type (and version!) but also have a direct link to the seat map.
How to improve TripIt
- Fix that user interface. Show the most important info and have a button to show everything else. But only the info you actually have, not empty fields.
- Move confirmation number down to the passenger info so that you can tell which number is associated with each person. If there’s only one number, just repeat it next to each passenger.
- Move the check-in button down to the passenger info and have a separate button for each person. This should prevent the problem where it autofills multiple numbers in the confirmation box.
- Fix the problem where it thinks two different flights with the same number are non-stops. I can’t be the only person having trouble with this.
- Fix seat info.
What do you think? Are there things that bother you about these two services that I missed? Feel free to put you thoughts in the comments below. Just try to remember to treat others with respect, it’s just an itinerary manager so if somebody’s preferences don’t align with yours, it isn’t the end of the world.
The Wandering Engineer 
I don’t see ANY ads in my Tripit.,, NONE. Why is that? Are you using a browser adblock?
Hmm, that’s certainly odd since I see a ton of adds on my Tripit. I’m not using an Adblock but even if I was using one, it wouldn’t explain why you aren’t seeing ads and I am. Maybe you are using an adblock?
I am; Adblock Edge on Chrome
I’d post a pic of what I see, but I don’t think your website has that ability, correct?
Ironically, I see a handful of ads on my kayak.com site, lol. Adblock Edge doesn’t seem to block those.
My hotel check in and flights are still showing in the wrong order! Do you know how to change it or when it switched over to the right display order for you?
That sure is weird since mine are always correct now. You can manually fix things by going in and clicking edit for every item that is wrong and manually changing the time so that they don’t overlap.
I had to uninstall the kayak Android app due to it constantly crashing. I’ve notified kayak customer support who replied that the issue will be fixed in the next release. That can’t tell me when that will be, however. For now, I’m going with worldmate, although I’d prefer kayak.
I’ve had problems with Tripit when I’ve made changes to reservations. It used to alert me of a conflict and ask me which was correct. It stopped doing this. I made reservations earlier this year for a work trip and changed the dates, promptly forgetting about when I made the change a few months ago. Tripit merged both the cancelled and new dates and didn’t alert me of the conflict, saying that my trip started a day earlier. I only caught it a day before my flight when trying to check in. This is why I’m researching alternates to Tripit. How does Kayak handle reservation changes or conflicts?
For changed reservations, I just email the new one and it corrects things. Probably based off the confirmation number. For cancelations, it doesn’t seem to know what to do so I just manually delete the item.
I like to print out my Tripit itineraries and to keep them compact. But Tripit wastes an extraordinary amount of space printing much of the hotel information twice– once for when you arrive and once when you leave. It’s impossible to get rid of this repetition so often my itinerary goes unnecessarily long. Why do they do this?
I tested for my upcoming China trip Kayak, Tripit, Tripcase, and Worldmate – and I am sorry to say, that they are all poor. All lack of some standard features which I basically can’t understand as frequent traveller. Beside Kayak all of them lack of the feature seeing the original mail. This is SO important when something goes wrong on the trip to have quick access to. Simply can’t understand why they are saving money here (I believe saving disk space). Why the hell can you upload pictures(!) in TripIt but not upload a booking reservation as pdf? Kayak as well as Woldmate are way better in finding meta data (like seat information on Lufthansa flight tickets, address hotel booking emails from the hotel website – not from a big booking platform), TripIt clearly lacks here. On the other hand in Kayak more complicated receipts (like tour bookings in mandarin or flight bookings from China Eastern Airlines) are now stuck in the “email processing” phase for days – and you can’t manually match them like Tripit lets you do. Tripcase on the other hand neglects so complicated emails completely without notifiying you. All lack the key feature of showing the hotel addresses in the local language accordingly (in a way that the Google maps link which all have implemented works) although Kayak and Worldmate at least show the information.
Worldmate limits the characters in notes, which is the most stupid thing I have encountered in all those apps. Sorry, but why can’t I add a arrival information – just because Worldmate believes it shouldn’t be longer than 250 characters? The 250 are just a guess, because of course, they just show an error but not the number of chars which would be allowed!
All have a nicer UI as Tripit – it not just looks old fashioned, it is in some parts not very user friendly.
As summary: I need to use my old fashioned spreadsheet instead – I simply don’t want a third tool (I juse now Outlook and a spraedsheet) and the hope I had, that I can then skip the other two tools is not realistic. I just don’t get it, why such tools, which are now quite long on the market already, still lack on such basic features. This is a lack of understanding travellers and a lack of their CEOs beeing interested in a really helpful product – it seems, they are all just interested in selling your data.
I have started using this new one called TravelerBuddy. I love the interface and features, especially since it’s tailored for business travelers like myself. Maybe you can give that a review some time as well?
Traveler Buddy’s account signup sucks.. Can’t confirm my account to use it.. NEXT!!
Kayak My Trips is no longer what it used to be. The features described in this article do not reflect the Kayak app. It is no longer possible to share and collaborate with other Kayak My Trips users. Too bad!
27 reviews and “Installs – 1,000 – 5,000”. Seems you’re one of the few.
Are you affiliated with the app?
Thankyou for this post!! It has saved me a world of pain – Worldmate has just announced that it will be shutting down, and I quickly need a good alternative. I appreciate your clear comparison of the four (on your other post) and your update here. I will try Kayak based on this. I expect there will be many more Worldmate users coming your way soon…
Thanks for the in-depth comparison. I suspect you’re going to be receiving a lot more traffic now that Worldmate has announced they’re shutting down the app (https://www.worldmate.com). I’ve used it since back in the Blackberry Travel days, so I’m scrambling to find a quality replacement. I’m not sure if Kayak or TripIt will suitably replace the functionality and level of integration I had with Worldmate Gold and Outlook/Exchange, but I’ll test them both out and see how it goes.
I know this article talks about Trip it and Kayak but, at your previous article you talked also about Worldmate that just recently announced they will close the app. Of course, Tip it or Kayak looks a great substitute in my case for Worldmate but, most important for me would be to take off all my trips data from Worldmate to import into Trip it, Kayak or something else… Some suggestions?
I don’t know of anything other than manually resending it. Or… kayak and tripit have the ability to link your email account and it will scan through it and add everything automatically. I don’t do that because it makes me nervous but might be useful for you.
Same^
My Tripit Pro subscription just expired. I’m considering not renewing it for two reasons:
1. Flight times that change aren’t updated until 48 hours before departure, even if the change actually happens months in advance.
2. I get notices telling me I could save money by cancelling and rebooking at a lower price, even taking the cancellation fee into account. The problem with this is that if I’ve paid for features such as extra legroom or early boarding, the Tripit thinks my base price was higher than it was. So, useless.
Does Kayak do better on either of these?
Would have liked to see a cruise included in the test. I haven’t looked at Kayak yet but I moved from Worldmate to Tripit for the easier way of adding cruise details.
That would have been a good test. Unfortunately, I’ve never been on a cruise so I didn’t have one to test.
I had to manually add my cruise and the ports of call in tripit in shows as a cruise however in worldmate I had to add as transportation and accomodation for each port as worldmate doesn’t have the ability to add a cruise.
Thanks for the article. I used to use Tripcase without any problem. However recently upon submitting my itineraries via email, Tripcase only shows the return flights (Delta email receipts). I am trying Kayak now. However, the wrongly showing the airport for my stops. Instead of showing Minneapolis-St. Paul (MSP), it shows Mout Pleasant (MPS). And there is noway to correct it.
If you click on the trip, you can then click the three dots in the upper right corner of the flight and click edit. There you can change anything. You should also hit the report inaccuracy button so that their algorithm improves.
Hi thank you for these articles. I was looking for a better alternative to Tripit, so I tried Kayak per your comments above. What I found that was a deal breaker for me is that I have not found a way to attach anything to the Kayak trip detail items. For ex, when I make reservations for a tour, or buy tickets for an event, I attach an image of the ticket with the QR code or bar code to the Activity in Tripit, but I didn’t see an option to do that in Kayak. Tripit definitely has some room for improvement, but that is a great function that has been helpful many many times. Thanks!
Store the image in Google Drive or One Drive, etc. then copy the link to that image and paste it in teh notes section for each trip in Kayak.