The Best New Ways to Book Your Flights

Chances are, you're stuck in a flight-search rut. And chances are even better that it’s costing you money, time, and energy. For years, the online travel-booking space has been dominated by a handful of brands: Expedia, Kayak, Orbitz, and Priceline.com. They revolutionized the business, giving anyone the ability to book airline tickets without the help of a travel agent or airline rep. Now comes a new crop of powerful flight-finding websites and apps. Armed with machine learning, natural language processing, and big-data capabilities, they offer novel ways to find cheap fares, plan better trips, and save time. Here are the ones you need to know about the next time you log on.

HelloGbye

For escapes with your entourage

The promise: HelloGbye lets you type out (or, on the mobile app, dictate) a complicated itinerary involving multiple travelers, cities, hotels, and more—as if you were talking to a travel agent. Then the app makes sense of it all and suggests options to suit your needs.

The process: Natural-language parsing helps the site break down instructions like, “I need to fly to Miami for three days on November 15” or, “Amy, Lindsay, and I will meet in Cancún on December first.” It then finds flights and hotels for each passenger based on his or her HelloGbye profile—which can be set up in just a few minutes.

The results: HelloGbye’s user-friendly design is a triumph; it really did allow us to plan and book a trip for multiple travelers in a flash. The site identifies where each person is coming from, along with the flight and the hotel they’re likely to want. Then it organizes suggested itineraries on a calendar display. Don’t like the recommendations? Comparison-shop within the same browser tab. Also easy: splitting the bill with family and friends.

The caveat: The tool is still in early stages, so phrases can be misunderstood.

Cleverlayover

For spending time to save money

The promise: Plug in your departure and arrival airports, and this metasearch site will show you nonstop flights as well as what the company calls “clever layovers”: money-saving itineraries that involve plane (and airline) changes.

The process: The lightning-quick algorithm tries to find cheaper fares by combining flights from non-partner airlines—for instance, flying from Boston to Paris on one airline and then from Paris to Prague on another. You can also ask the site to put together itineraries that let you spend several days in a connecting stop.

The results: According to the company, roughly 30 percent of searches discover a layover bargain, with offbeat and secondary destinations working best. In our tests, only 20 percent of the results needed a strategic stop—and those itineraries weren’t always cheaper. The site saved us $674 on a route from Cleveland to Myanmar, but a flight between Boston and Dubrovnik was less expensive on CheapOair. There was, however, a surprising twist: itineraries that were also available on other sites often cost up to $500 less through CleverLayover.

The caveat: Using multiple carriers can make it difficult to change your flights.

Flykt

For discoveries on a budget

The promise: This streamlined tool (pronounced flaked) starts with a simple but essential question: How much do you want to spend? Indicate your budget, departure point, and interests (gastronomy or the beach, say); then add keywords to further refine the search (perhaps vegetarian or surfing). Flykt will present up to six destinations—plus flights and hotels—that fit your criteria.

The process: Instead of routes and carriers, Flykt is about places. Its team obsessively compiles data on cities around the globe—upwards of 500 when the site launched in October—and follows trends in order to understand what kinds of travelers are going where. The company leverages relationships with low-cost regional carriers to offer affordable itineraries, but finding the cheapest price isn’t its main advantage; it shines at intuiting what’s right for you while screening out too-expensive options.

The results: Flykt’s recommendations were surprisingly sharp: for two New York–based food lovers seeking a romantic, last-minute trip for under $2,800, it suggested itineraries in Stockholm, Vancouver, and Porto, Portugal. A smaller budget and shorter time frame yielded Asheville, North Carolina. Some results missed the mark (Altamonte Springs, Florida, isn’t yet a foodie hot spot), and there were some overly cumbersome itineraries (we’ll pass on the three-stop route to Split, Croatia). But all the ideas came in under budget, enough that we could tweak flight and hotel choices without running out of funds.

The caveat: There’s no mobile app yet.

DealRay

For impulsive travelers

The promise: For $9.99 a month, DealRay will send you a text whenever it detects hard-to-resist deals on flights (think New York to Paris for $300).

The process: The company uses proprietary algorithms and manual research to scour the Internet for big price drops and “mistake” fares (deals that stem from computer glitches or data-entry errors). Unlike with other fare-alert services, you can specify a point of departure. The alerts spotlight any flights that have been deeply discounted—and verified as bookable by DealRay’s staff, so you don’t waste your time on too-good-to-be-true offers.

The results: Of the 10 deals we received in roughly three months of testing, all were exclusive to DealRay—we didn’t see them anywhere else. Four were the result of airline blunders, including $300 Iberia fares from New York to Tel Aviv and Casablanca. Two others highlighted $99 international flights on Wow Air, which regularly promotes such prices but rarely makes them available. All of the alerts included step-by-step directions for finding and completing the bookings.

The caveat: Fares can expire within a few hours and often only apply to limited departure dates. Also, while it is totally legal to book a mistake fare—even if it’s pretty obvious that someone misplaced a decimal point—at press time the Department of Transportation was allowing airlines to cancel those reservations at their discretion.

News from the old standbys

Fresh features from familiar travel-booking sites.

Google Flights now lets consumers search for flights to and from entire regions rather than just specific cities. It also gives you the ability to identify the “best flights,” weighing price and convenience.

Orbitz recently launched a portal on its app where you can book package deals that combine flights and hotels. Also look for “mobile steals”—mobile-only discounts of up to 50 percent.

Priceline.com created apps for the Apple Watch and Android Wear earlier this year. On Apple, you can access your itinerary on your wrist or find last-minute hotel deals; on Android, you can find useful places like pharmacies and ATMs near your hotel.

Expedia has started delivering “happiness” scores for flights, factoring in legroom, Wi-Fi availability, in-flight entertainment options, and more.

For our list of the best travel apps and websites, head this way.