For a long time, there have been two polar opposite ways to plan a trip: outsource the bookings and nitty-gritty details to a travel agent, or spend countless hours combing through flight options and hotel deals, planning meals and itineraries. But with the rise of chatbots — specifically those with Facebook Messenger integrations — there’s a new in-between.

Flight-finding bots from sites like Kayak and Hipmunk make clinching the best deal a breeze, simplifying the hunt with a conversation-driven interface. Ditto bots like TripAdvisor’s, which provides insider tips and recommends coffee shops, restaurants and things to do.

Granted, these bots are only able to process small amounts of information at once and are incapable of automatically applying the necessary filters for a very specific question like “Find me the cheapest available nonstop flight to Chile during the month of October,” never mind passing the Turing test. Nevertheless, they remain convenient. The conversation-driven interface is more streamlined than scrolling through an ad-laden, number-heavy website. When planning a trip, they’re more conducive to discovering new destinations; once you’re on the ground, they fall somewhere between local friend, hotel concierge and travel agent.

Snaptravel


Most Human: A booking bot with real, live customer service representatives standing by to help as needed. SnapTravel pulls data from dozens of online travel sites to find the best hotel deals. The human element comes into play once you’ve arrived at your destination; reps can coordinate any necessary hotel room changes or specific check-out requests and will always ask for a free upgrade on your behalf.

Kayak


Best for Getting There: To lock in flights, hotels, car rentals and select experiences (like guided tours) all at once, Kayak is your go-to. While it’s most effective when booking with a destination in mind, the bot can also provide more spontaneous or price-driven recommendations, spitting out quick answers to questions like “Where can I go for $250?” and “What can I do in Chicago?” Kayak’s bot also provides real-time updates on flight delays and gate changes.

Hipmunk


Best for Destination Inspiration: Hipmunk’s Messenger bot is best used to pursue a good deal. It lists the “least agonizing” flights according to price cap, destination and date range. You can apply filters for airlines and the number of layovers, and fare alerts can be set for select routes. But for those looking to take a trip without a destination in mind, Hipmunk’s algorithm provides some very compelling responses to requests like “I want a beach destination for July Fourth” and “I want to go camping in September.”

TripAdvisor


Best for Building an Itinerary: Combing through reviews and ratings of restaurants, activities, bars, coffee shops and more, TripAdvisor’s bot acts as a local guru. It won’t provide any definitive recommendations or make restaurant reservations for you, but its filters — price, specific neighborhood, area of interest — as well as its ability to save items, are helpful for zeroing in on options and crafting a game plan.

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