Well over 30 years ago, I had just started a new job when the boss strolled by — and out of the clear, blue, friendly skies asked me to make an airline reservation for him. I had little to go on, just the destination airport, travel days, and some rough travel times. I had no idea about his airline preferences, much less whether he preferred window or aisle seating.
Back in those days, you called a travel agent and stepped through the process of getting a ticket delivered to your door. Or, if you wanted to make sure the travel agent was on target, you could do a little of the legwork yourself first by looking up flights in the Official Airline Guide, a thick book with tiny phonebook type.
I eventually located a suitable set of flights and passed the info on to his assistant, who dutifully typed the itinerary on an index card for him to carry in his pocket.
How times have changed! Airlines now offer booking Web sites, their own apps, and mobile boarding passes. Plus, you can quickly and easily research flights, hotels, rental cars, and more with apps that are dedicated to that purpose. But two things haven’t changed: travel is still a very personal thing, and I’m still looking for the best way to keep all my travel info in one place. The index card approach just doesn’t cut it today.
Over the years, I’ve done a fair bit of traveling, both business and personal, and here’s what I’m looking for in a travel management app:
There are a number of candidates in the App Store, but these five stood out: Google Trips, App in the Air, Kayak, TripCase, and TripIt.
All the apps have most of the same basic features. After you set up an account with their service, they scan your email inbox for details about a trip (flight times, hotel bookings, etc.) and build an itinerary for you. With most of the apps, you can also either forward booking emails you’ve received to a standard address to create the itinerary or enter the details manually.
Once the trip is in place, the app generates additional information such as airport info and local weather, and adds it to your itinerary. You can share the trip with others, add the details to your calendar, and receive trip-related notifications such as check-in times and flight delays.
If you’re on the move, your travel plans should move with you in the most convenient way possible. So all these apps make their data accessible on different devices, and most of them extend a subset of their features to the Apple Watch. Only Google Trips lacks an Apple Watch app, and of the other four, only TripIt doesn’t include a complication that can show at-a-glance flight details such as gate information, time to check-in, and baggage claim carousels.
Also, all but Google Trips include a Messages app, which can be helpful if you regularly need to share trip details in conversations.
Beyond these basics, there’s plenty of room for each app to differentiate itself, be it through the use of crowdsourcing, packing lists, flight trackers, or the ability to book travel from within the app.
In short, there’s probably an app in this group with features that will best fit your needs. We can’t cover every nuance in this article, but let’s take a look at some of the more interesting features.
Google Trips -- Google is nearly ubiquitous and its services are generally regarded as being top tier. Plenty of people rely on Google while planning and booking travel plans, so organizing travel information with the free app seems like a reasonable extension of its services.
Setup is simple. You allow the app to access your location while using it, allow notifications about your trip to be sent to you, and sign in with your Google account, giving the app permission to detect past and future trips from information it can find in your Gmail account.
From there, the app’s real strength appears, as it suggests things to do, creates customizable daily itineraries of places to go, provides food and drink recommendations, covers how to get around in the local area, and offers “need to know” facts such as emergency numbers, shopping, and tipping info. Plus, it lets you download all this information from Google for offline viewing. Making use of Google’s vast collection of the world’s knowledge is easily the strongest part of the app.
However, Google Trips is the newest of the five apps in the group and lacks many features that the others have.
If you don’t use Gmail as your primary email provider, Google Trips won’t be nearly as useful. You can add a trip manually, but unlike the other services, Google doesn’t offer a standard email address to which your booking emails can be forwarded to create an itinerary.
Many of the other four apps offer at least some notification options. Google Trips itself contains no notification settings within the app, just the opportunity during setup to enable them — but offers no specifics as to what the notifications are. Also, in the current version of the app, you can’t share itineraries, which may be a deal-breaker for many people. There’s also just an iPhone app; no iPad, Apple Watch, or Messages app.
And now a confession: I don’t use Google’s services much. As such, Google Trips has limited value for me because it relies heavily on harvesting flight data from a Google account. As the new app on the block, it’s also missing basic features that the other more mature apps have. But if you’re waist-deep in the Google ecosystem, the way the app makes it easy to explore your destination might make it the ideal solution for you or as a companion to one of the other apps.
App in the Air -- Not surprisingly, given its name, the free focuses on managing air travel but has recently begun to branch out by allowing you to include hotel and car rental details in your itinerary.
Flights are organized into cards. Tapping a card reveals all the details from a generous selection of up to 16 customizable widgets, including a timeline, airport and airline info, an online check-in form, maps, wait times, hotel and car rental details, and more.
Unique among the five apps, App in the Air presents flight information in a timeline of four segments: Check-in, Boarding, Take-off, and Landing. Knowing these four items in a flight’s timeline can help you prepare for your flight and keep family and business associates in the loop as to your schedule.
You can also allow App in the Air to access your calendar to import existing flights and access your contacts for itinerary notifications.
App in the Air offers plenty of push and text alerts that you can activate individually (including one for in-flight exercises), but you’ll need a subscription to make them work. Other premium features ($29.99 per year with a free 14-day trial or $49.99 for lifetime access) include a family subscription and unlimited auto check-in. As with many freemium apps, it sports a long list of in-app purchases that range from disabling ads for $0.99 to a lifetime subscription for flight alerts for $49.99.
Other notable features include:
You can subscribe family and friends to flight alerts too, keeping them in the loop should your itinerary change.
Some of the widgets are innovative. One allows you to track your luggage on American Airlines flights. The TSA Rules widget lets you enter an item and responds with rules about whether the item may be carried on board or must be stowed in checked bags. And sometimes widgets appear only if they are relevant; for example, the Uber widget shows up only if there’s service where you are.
If you enter your passport information, App in the Air can theoretically check you in for flights automatically. I couldn’t get this feature to work, perhaps because I didn’t have an active subscription, but it would come in handy for airlines like Southwest that don’t assign seats in advance.
You can export trips to any of your calendars, which can save you the extra step of downloading flight itineraries from an airline’s Web site and adding them to your calendar.
You can import itineraries from TripIt. So if, for example, you want to switch from using TripIt or your company has standardized on TripIt, but you prefer the App in the Air interface or features, it’s easy to do so.
You can also import flight plans by scanning your boarding pass or from the boarding pass stored in Apple’s Wallet app; on the back of the pass, just tap Share Pass, then tap App in the Air.
If you’re into tracking your travel, let App in the Air do the heavy lifting. It can log miles, hours, airports, and more. You can also earn badges for your achievements. There’s even a whimsical award for Time Travel, but you’ll need to supply your own flux capacitor.
To help you get through airports more efficiently, App in the Air includes maps and crowdsourced wait times for check-in, passport processing, and security.
If you’re still using scraps of paper to track what to pack, you might like App in the Air’s editable packing list.
App in the Air can help you track loyalty points for airlines, hotels, rental cars, and other entities, but the feature is relatively limited, particularly for U.S. airlines. It also requires creating yet another account, with.
There’s a lot to like in App in the Air and there’s likely more to come. The cost to enable the additional features provided by the subscription isn’t cheap. But if you fly regularly, the lifetime subscription is probably a worthwhile bet to place, since the app receives regular feature updates. I highly recommend App in the Air.
Kayak -- Now owned by Priceline, the free app boasts a long list of travel-related features. Most notably it helps you find and book flights, hotel rooms, and rental cars; and provides a top-notch interface.
You can filter your searches by a multitude of categories, including price, non-stop flights, car type, hotel brands, amenities, and much more. When the search results are presented you can book them, or in the case of flights and hotel rooms, set up a price alert. Kayak does a nice job suggesting whether it makes sense to buy an airline ticket immediately, or to wait a while and see if prices come down.
Kayak takes travel planning a step further with its Explore feature. You set parameters for your trip, such as a budget, time of year, location, and activities, and Kayak responds with suggestions.
Along with all the basics, once a trip is created, you can also add related events and details such as meetings, dinners, and local transportation, a plus for business travelers.
One-upping App in the Air, Kayak automatically creates a calendar feed with all your itineraries, so if information about the trip changes, it’s automatically updated in your calendar. To get the URL for the calendar feed, you’ll need to log in to Kayak on the Web and look in.
Kayak recently added the capability to import booking confirmations automatically from Gmail accounts. That’s a nice improvement, but like Google Trips, it works only with Gmail while App in the Air and TripIt can sift through the inboxes of many more email services.
Kayak provides a number of other niceties:
Kayak’s flight tracker isn’t limited to just the flights you travel on. You can track any flight you want; that’s helpful if you’re the one making the airport run to pick up Grandma.
It can automatically share all new trips with others via email. Kayak even provides the option of letting others edit the trip, which would be useful for an administrative aide to add a meeting for a traveling boss.
When you add a hotel manually to an itinerary, Kayak automatically fills in the address, phone number, and URL for the property. Hotel details include a section on nearby restaurants (courtesy of OpenTable, another Priceline company) and a Show Driver button that displays the hotel address to show a driver if there’s a language barrier.
In addition to email, SMS, and notifications, Kayak can also send flight status alerts via Facebook Messenger.
You can use autofill for your contact info, pulling your data out of your Contacts app with a couple of taps. These autofill settings can be kept in sync through iCloud. So if you change any of your contact info — say, your home address — you can change it on one device and let iCloud handle the syncing with the rest of your devices.
Kayak is the only app of the bunch that has an Apple TV app. That makes it easier for people to do travel planning together… and I’ll bet those shots of the French Riviera on a 60-inch TV screen are enticing.
While it’s a good fit for personal travel, Kayak also works well for business travelers, who can use the app to include meetings and other events in their itineraries, follow flight plans of co-workers, and allow others to edit their trips. If you’re looking for a single app to plan, book, and manage travel, you can’t go wrong with Kayak, especially given that it’s entirely free.
TripCase -- Our next entry is, which is owned by  — perhaps the first company to get into the real-time, computer-based air travel booking business. TripCase provides a full array of travel management tools, including several that target business travelers.
Unlike the other apps, after you set up an account and complete your profile (which you must do to use TripCase), TripCase doesn’t search through your email for travel info and automatically build itineraries. Instead, you either:
Forward email confirmation messages with travel info to or enter the details manually.
Use a TripCase affiliate to do bookings, in which case, the details will automatically be added to your account. An affiliate is any airline, travel agency, company travel department, or supplier that uses TripCase’s technology to automatically import reservations into a traveler’s TripCase account. Unfortunately, there’s no list of affiliates to be found online or in the app, so your results may be hit-and-miss.
Neither of these is as friction-free as having the app look through your inbox. And the mystery surrounding the affiliates isn’t good, either — two demerits.
Once you have a trip built, you can add activities such as meetings, restaurants, and attractions, and the app provides access to Uber, airport maps, weather, and other information right within the trip. Separate screens provide links to restaurants and things to see and do at your destination.
TripCase offers the usual trappings, such as push/email alerts and the capability to share trips with others, although updates other than flight changes are not sent automatically to people you designate. However, if those people sign up for TripCase, your trip appears in a convenient Following list, with full updates — a handy feature for business travelers.
On the calendar side, TripCase lets you do a one-time import of your trips, or it can create a calendar feed that will update itself.
Of course, there’s more:
TripCase shows a Tripfeed in its details screen that may include helpful information such as a link to an airport map or ads that suggest you buy various trip-related items such as travel insurance, an audiobook for the flight, and an airport lounge ticket. Unfortunately, there’s no way to turn off the ads with an in-app purchase.
TripCase offers (for a $5.99 in-app purchase good for a year after a 1-month trial period) the option of storing images of your receipts as PDF files to save time when filling out expense reports, a welcome feature for business travelers.
You can use TripCase to search for alternate flights for future trips you have planned.
An Apple Watch app displays an itinerary as well as nearby locations. But while the complication appears in the list contained in the Watch app, it would not appear as an option under the Faces section of the app.
TripCase is clearly built for business travelers. But it feels incredibly dated in terms of look and feel and lacks too many standard features that its counterparts have. Unless your company mandates its use, I recommend looking elsewhere because there are better options.
TripIt -- As with a couple of the other apps, is part of a larger company’s travel portfolio. It’s owned by , which provides travel and expense management services to businesses. Concur also owns , another app that can book flights and hotels. Combine the two and you have a travel solution aimed squarely at business travelers.
TripIt has all the basics covered and, like Kayak and TripCase, you can manually beef up your itineraries with additional travel plans, such as train or ferry trips, and activities like meetings or theater outings.
TripIt provides a calendar feed that maintains updated itineraries in your calendar app. You can share trips, which isn’t unusual, but TripIt allows you to share only parts of your itinerary, so you could choose to share flight info but not hotel arrangements, for example.
For $49 per year, you can upgrade to TripIt Pro and get flight status alerts by text or email, reward tracking with a number of vendors, check-in reminders, automatic trip sharing, flight refund monitoring, and more. That cost is higher than what other apps charge, but you can try TripIt Pro for 30 days for free.
TripIt is big on social via its Network feature, offering a dizzying array of options, including:
You can post travel plans to LinkedIn, Facebook, Yammer, and Salesforce Chatter.
You can add connections to other people either manually or through your Google or Yahoo email accounts. Once connections are made, you and your connection can each see summaries of each other’s trips. In addition, TripIt can spot when connections are near each other when travel plans overlap.
TripIt Pro users can create an “inner circle,” members of which see your detailed itineraries and get automatic notifications when you create new trips. People in your inner circle do not have to be TripIt Pro users and trip information is shared only from you to them, not the other way. You can optionally choose to allow an inner circle member to edit your trips, which might be handy if your assistant regularly handles such details anyway. You can designate individual trips as private to avoid sharing trip information, even with your inner circle.
And that’s not all:
TripIt stores an extended set of profile info, including space for travel documents like your passport, TSA Pre, CLEAR, and driver license. It can also store travel-related contacts such as emergency contacts, house sitters, boarding kennels, and so on.
Like App in the Air, TripIt can track basic travel stats. There are no medals for achievements, though.
You can create groups for free. People with email addresses with the same domain (think companies) can use a shared calendar to coordinate travel schedules and see other group members’ trips and locations on a map. Trips can also be made private.
For $29 per month for up to 10 users (with prices scaling up to $159 per month for 100 users), an organization can subscribe to TripIt for Teams, which offers the group features above along with team-wide spending reports and a travel dashboard that shows all of the team’s travel plans in one place. It’s best suited for an organization that has a department arranging travel for others.
TripIt is solid on all fronts and works equally well for both personal and business travel. If you travel a lot, the Pro features are a must-have. Unless you have a big problem with using a separate app to book travel, TripIt has you covered.
Book It -- Let’s wrap it up. All five of these apps can work for personal travel, but Kayak, App in the Air, and TripIt are clearly ahead of Google Trips and TripCase thanks to a more complete set of features.
Kayak and TripIt are best suited for business travelers given their capability to add other activities to trip itineraries, and the inclusion of TripIt’s $49 Pro package gives it a slight edge over Kayak for business travelers.
With its features that appeal to groups and teams, TripIt is the best option for organizations that need to manage complex travel calendars and costs, bolstering its position as the best app for business travelers.