On the return leg of a short business trip, you can choose between 1) a flight that leaves mid-morning but includes a stop, for a total duration of 7 hours, or 2) a direct flight that leaves around 2 p.m., lasts only 4 hours, but gets in slightly later than the first flight. Which one is better? Oh, also: Flight No. 1 has onboard Wi-Fi, while Flight 2—which costs $50 more—has no Internet but does feature seat-back TV. Made your decision? Actually, hold that thought, because you still need to wade through labyrinthine seat-assignment, rental car, and hotel options (big room near the airport that earns you bonus miles, or small one at the conference hotel with no miles?).
The gargantuan $439 billion U.S. travel industry is an amazing fount of innovation, but for the most part, its new sites and services—nimble upstarts such as Hipmunk, Routehappy, Superfly, and HotelTonight are today's trendy alternatives to one-time innovator Kayak or first-gen warhorses like Expedia—serve that noisy, nitpicky niche of power travelers. Like me. We are in a golden age if you want to manage extremely complicated multi-leg journeys or obsess over such trip details as the legroom measurements for every available airplane seat. But for all the access to comprehensive trip data, almost 20 years of advancements still have not brought us close to mimicking the glory days of yore, when a professional human who understood you and your destination could create an itinerary for you in a jiffy.
The online travel business, though, is ripe for the next level of transformation—from the machine acting merely as your tool to the one that serves as your agent.
Imagine if, instead of just showing you a list of flights in response to a query, travel sites were personalized and predictive. Say you schedule a meeting in Houston next Tuesday. Your travel service, recognizing the meeting in your calendar, scans hundreds of available flights for those that conform to your schedule and your preferences. If you only fly United because you're a miles junkie or would rather spend $200 extra for a direct flight, this service—which has learned your preferences by reviewing your travel history—would know that and could even go so far as to book your trip without your input.
This is still fantasy (mine), but "a lot of what we used to get from travel agents can be filtered through machines," says Scott Mackenzie, who runs the travel-advice site Hack My Trip and is an expert on the tips and tricks of airline reservations. He notes that today's most advanced travel sites do remember some users' preferences; with machine-learning hothouses like Google getting deeper into this business, booking algorithms are likely to get more intelligent soon.
If you don't want to wait for the travel singularity, you can take advantage of the web's booking ninjas without having to become one. Flightfox is a startup that crowdsources complicated trip plans. If you'd like to find the best fare for a trek through South America—plus tips on cities, hotels, and sights—you can post your request on the site. More than 1,000 travel-industry aces compete to meet your needs; you choose one, pay a small fee, and he or she finds you the best possible trip. Sound familiar?
[Illustration by Mario Wagner]
A version of this article appeared in the September 2013 issue of Fast Company magazine.