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AI Infrastructure · Top 10

The 10 Best AI Tools for Trip Itineraries in 2027

By Kory White · Updated Oct 2026 · 6 min read
Google Gemini
Direct answer

Google Gemini is the best AI tool for trip itineraries: it builds a multi-day plan grouped by neighbourhood from real-time Google Flights and Hotels data, and it is free to try. Tripadvisor’s AI Trip Builder is #2 for editable day-by-day plans, and Mindtrip is #3 for a planner that learns your style.

At a glance

#PickPriceBest for
1Google GeminiFree to try (“Try Gemini free of charge”); the page lists no subscription pricesTravelers who want an itinerary tied to live flight, hotel and map data at no cost
2Tripadvisor AI Trip BuilderThe Tripadvisor app is listed as Free on the App Store; no paid plan is publishedTravelers who want a day-by-day plan built around Tripadvisor’s reviews and photos
3Mindtrip AI Travel PlannerFree on the App Store; its description calls the app “totally free”Travelers who want a planner that remembers their tastes and tracks prices
4WanderlogFree to download; Wanderlog Pro in-app plans are listed at $14.99 monthly and from $27.99 to $79.99 annuallyGroups that want one map-based itinerary with real-time collaboration
5LaylaPlanning is free, with “no subscription or planning fee”; you pay for the travel you bookTravelers who want AI planning backed by a human expert and a price guarantee
6Trip.com TripGenieFree (the page title calls it a “Free AI travel Q&A assistant”)Travelers who book flights and stays on Trip.com and want chat-based planning
7KAYAK Ask AINot published; the announcement mentions no costDeal hunters who want itinerary chat next to live flight and hotel prices
8ChatGPT for TravelFree is $0 per month; Go is $8, Plus is $20 and Pro is from $100Travelers who want a general chat assistant for itineraries, destination choices and travel-day prep
9Expedia AI Trip PlanningNot published; the Expedia app in ChatGPT is listed for logged-in users on Free, Plus and Pro ChatGPT plansTravelers who already book on Expedia and want chat-based planning
10iplan.aiNot published; the site states no priceTravelers who want a quick questionnaire-based itinerary on a small, focused tool

Pick by what you want

Best overall
Google Gemini
Best editable day-by-day plan
Tripadvisor AI Trip Builder
Best map-first app
Wanderlog
Best with a human expert
Layla
Best for comparing prices
KAYAK Ask AI

The ranking

1

Google Gemini

Google Gemini
Answrs VerdictThe best free itinerary builder with live travel data.
Price: Free to try (“Try Gemini free of charge”); the page lists no subscription pricesItinerary: Builds a multi-day itinerary grouped by neighbourhood and helps map out the spots you want to visitLive data: Pulls real-time options from Google Flights and HotelsWhen plans change: Finds alternatives in Google Maps when bad weather or a closed venue disrupts a dayBooking: Finds and compares options, then links you out to complete the booking

Google Gemini builds a multi-day itinerary grouped by neighbourhood and helps map out the spots you want to visit. It pulls real-time options from Google Flights and Hotels, finds alternatives in Google Maps when weather or a closed venue disrupts a day, and links you out to complete a booking. The page says to try Gemini free of charge and lists no subscription prices.

Go ifTravelers who want an itinerary tied to live flight, hotel and map data at no cost
Skip ifYou want to book inside the same app
Why #1 over #2: It pairs the itinerary with live flight, hotel and map data, where Tripadvisor’s builder leans on review content.
2

Tripadvisor AI Trip Builder

Tripadvisor AI Trip Builder
Answrs VerdictThe easiest editable day-by-day plan from a review site.
Price: The Tripadvisor app is listed as Free on the App Store; no paid plan is publishedItinerary: Creates personalized itineraries with OpenAI’s generative AI: enter a destination, dates, companions and interests, and get a day-by-day plan you can save, edit and shareSaving: Reviews, photos and other content found while planning can be saved to a TripLaunch: Announced July 19, 2023 as a public beta for US users

Tripadvisor’s AI Trip Builder creates personalized itineraries with OpenAI’s generative AI: you enter a destination, dates, companions and interests and get a day-by-day plan to save, edit and share. Reviews, photos and other content found while planning can be saved to a Trip. It was announced on July 19, 2023 as a public beta for US users, and the app is listed as Free.

Go ifTravelers who want a day-by-day plan built around Tripadvisor’s reviews and photos
Skip ifYou need proof of current coverage outside the US
Why #2 over #3: Its plans are fully editable and shareable, which Mindtrip’s learning assistant does not emphasize.
3

Mindtrip AI Travel Planner

Mindtrip AI Travel Planner
Answrs VerdictThe best assistant that learns how you travel.
Price: Free on the App Store; its description calls the app “totally free”Learns your style: Remembers how you like to travel so you do not start from scratch each timeBuild and Watch: Build keeps itineraries, ideas and bookings in one place; Watch tracks price drops and flight changesGroups: Group chats and shared, editable collections and itinerariesReviews: 4.7 out of 5 from 854 ratings on the App Store

Mindtrip remembers how you like to travel so you do not start from scratch each time. Build keeps itineraries, ideas and bookings in one place, Watch tracks price drops and flight changes, and group chats and shared, editable collections support travel with others. The App Store lists it as free, with 4.7 out of 5 from 854 ratings.

Go ifTravelers who want a planner that remembers their tastes and tracks prices
Skip ifYou want a pricing page that explains paid tiers
Why #3 over #4: It remembers your taste and tracks prices, where Wanderlog focuses on the map.
4

Wanderlog

Wanderlog
Answrs VerdictThe best map-first itinerary app.
Price: Free to download; Wanderlog Pro in-app plans are listed at $14.99 monthly and from $27.99 to $79.99 annuallyAI: Its site says the planner is “powered by our trip planner AI” and gives personalized suggestions based on your itineraryRoute: Optimizes your route, which suits road tripsPro features: Pro unlocks offline access, unlimited attachments, flight deals and export to Google MapsReviews: 4.9 on the App Store and 4.7 on Google Play

Wanderlog says its planner is powered by its trip planner AI and gives personalized suggestions based on your itinerary. It optimizes your route, which suits road trips, and Pro unlocks offline access, unlimited attachments, flight deals and export to Google Maps. It is free to download, with Pro in-app plans listed at $14.99 monthly and from $27.99 to $79.99 annually. It rates 4.9 on the App Store.

Go ifGroups that want one map-based itinerary with real-time collaboration
Skip ifYou want a single published price for Pro
Why #4 over #5: Its map-and-route view suits road trips, which Layla’s expert-led booking does not target.
5

Layla

Layla
Answrs VerdictThe best mix of AI planning and human booking.
Price: Planning is free, with “no subscription or planning fee”; you pay for the travel you bookExpert check: A travel expert checks and books the trip, with trips finalised within 48 hoursGuarantee: Package price guarantee on the total package price, with nothing added on top when her travel experts bookRoam Around: Roam Around, the AI itinerary planner, is now part of LaylaReach: 100+ countries explored and 15+ languages spoken

Layla is built around your dates, budget and style, and a travel expert checks and books the trip, with trips finalised within 48 hours. Planning is free with no subscription or planning fee; you pay for the travel you book, and a package price guarantee applies. Roam Around, the AI itinerary planner, is now part of Layla.

Go ifTravelers who want AI planning backed by a human expert and a price guarantee
Skip ifYou only want a free itinerary with no booking step
Why #5 over #6: A human expert checks the trip, which KAYAK’s chat does not offer.
6

Trip.com TripGenie

Trip.com TripGenie
Answrs VerdictA free chat assistant tied to Trip.com booking.
Price: Free (the page title calls it a “Free AI travel Q&A assistant”)Itineraries: Gives tailored travel advice and customized itineraries that match your travel styleExample prompt: “Can you suggest a 3-day family trip in America?”Booking: Says booking flights and stays is a breeze: tell it what you need and it handles the rest

Trip.com’s TripGenie gives tailored travel advice and customized itineraries that match your travel style, and says booking flights and stays is a breeze. The page’s example prompt asks for a 3-day family trip in America. It is labelled a free AI travel Q&A assistant.

Go ifTravelers who book flights and stays on Trip.com and want chat-based planning
Skip ifYou want details on how booking works, which the page does not explain
Why #6 over #7: It is free and tied to Trip.com booking, where KAYAK’s page publishes no price.
7

KAYAK Ask AI

KAYAK Ask AI
Answrs VerdictThe best chat for comparing prices while you plan.
Price: Not published; the announcement mentions no costChat: Ask questions in natural language and refine the trip in real timeLive results: Flight, hotel and rental car results update live alongside the conversationPrices: Shows up-to-date prices and bookable options from hundreds of travel partnersAnnounced: May 14, 2026

KAYAK Ask AI lets you ask questions in natural language and refine the trip in real time, while flight, hotel and rental car results update live alongside the conversation. It shows up-to-date prices and bookable options from hundreds of travel partners. KAYAK announced it on May 14, 2026 and mentions no price.

Go ifDeal hunters who want itinerary chat next to live flight and hotel prices
Skip ifYou want a saved day-by-day plan more than search results
Why #7 over #8: It shows live bookable prices beside the chat, which a general chatbot like ChatGPT does not.
8

ChatGPT for Travel

ChatGPT for Travel
Answrs VerdictThe most flexible general assistant for trip ideas.
Price: Free is $0 per month; Go is $8, Plus is $20 and Pro is from $100Walking itinerary: Example prompt: “Give me an itinerary for New Orleans today using this list of places as reference”, as a path that is easy to walkDestination choice: Example prompt compares San Juan and Cartagena for spring break, with pros and consTravel day: Example prompt asks for a real-time travel readiness report covering security wait times, food and weather

OpenAI’s travel page for ChatGPT shows prompts for a walking itinerary in New Orleans, a San Juan versus Cartagena comparison and a real-time travel readiness report. Free is $0 per month; Go is $8, Plus is $20 and Pro is from $100.

Go ifTravelers who want a general chat assistant for itineraries, destination choices and travel-day prep
Skip ifYou want a planner that saves and maps the trip for you
Why #8 over #9: It handles open-ended itineraries and comparisons, where Expedia’s ChatGPT app centers on searching and booking.
9

Expedia AI Trip Planning

Expedia AI Trip Planning
Answrs VerdictThe planner that ends in an Expedia booking.
Price: Not published; the Expedia app in ChatGPT is listed for logged-in users on Free, Plus and Pro ChatGPT plansIn ChatGPT: Refine details, explore dynamic results and complete your booking; results show pricing, availability and rich visualsSaving: Save options to Trip Planner from Expedia with the heart icon on stays or price tracking on flightsIn the app: Beta announced April 4, 2023: an open-ended conversation in the Expedia iOS app, with hotels discussed saved to a tripRomie: Announced May 14, 2024 as an alpha on EG Labs, with Group Chat Trip Planning and Building Your Itinerary

Expedia’s app in ChatGPT lets you refine details, explore dynamic results with pricing and availability, and complete your booking, and you can save options to Trip Planner from Expedia. Its own app got an open-ended chat beta on April 4, 2023, and the Romie assistant was announced on May 14, 2024 as an alpha with itinerary building. No price is published.

Go ifTravelers who already book on Expedia and want chat-based planning
Skip ifYou want a full multi-day itinerary builder, which its ChatGPT page does not describe
Why #9 over #10: It connects planning to Expedia booking, which iplan.ai does not.
10

iplan.ai

iplan.ai
Answrs VerdictA simple itinerary generator with a questionnaire.
Price: Not published; the site states no priceAI itinerary: “We’ll create your smart itinerary with the help of artificial intelligence”, ready “in a matter of seconds”Questionnaire: You give trip purpose, interests, companions, length of stay and budgetEditing and sharing: Move, modify or remove items and the AI adapts; itineraries can be shared privately or publicly

iplan.ai creates a smart itinerary with AI after a short questionnaire on trip purpose, interests, companions, length of stay and budget. It says results are ready in a matter of seconds, you can move, modify or remove items while the AI adapts, and itineraries can be shared privately or publicly. No price is published.

Go ifTravelers who want a quick questionnaire-based itinerary on a small, focused tool
Skip ifYou need published pricing or booking

How we ranked these

We ranked tools by how clearly their own pages show AI building a trip itinerary, then by cost to start, live travel data and booking, using each vendor’s official pages and app-store listings. Tripnotes was left out because Skift reported it was acquired by Dorsia and its website shut down. Booking.com’s AI Trip Planner was left out because its newsroom says the standalone planner is evolving into an embedded AI companion. Tripadvisor’s own AI Assistant page blocked our reader, so its facts come from its press release and App Store listing. Roam Around now sits inside Layla, so it is not listed separately. Facts are taken from each maker's own published information; check the official site before you buy.

Questions people ask

What is the best AI tool for planning a trip itinerary?

Google Gemini: it builds a multi-day itinerary grouped by neighbourhood, pulls real-time options from Google Flights and Hotels, and is free to try.

Are there free AI trip planners?

Yes. Google Gemini is free to try, Layla charges no planning fee, TripGenie is labelled free, and the Mindtrip and Tripadvisor apps are listed as free on the App Store.

How much do paid AI travel planners cost?

Most list no price. Wanderlog Pro appears on the App Store at $14.99 monthly, and ChatGPT lists Go at $8, Plus at $20 and Pro from $100 per month.

What happened to Roam Around?

Layla’s page says Roam Around, the AI itinerary planner, is now part of Layla, and its existing itineraries remain on roamaround.io.

Listed price per month of the paid plans in this list at a glance

ChatGPT Go8 USD
Wanderlog Pro (monthly plan)14.99 USD
ChatGPT Plus20 USD
ChatGPT Pro (from)100 USD
Listed price per month of the paid plans in this list, as published by each maker. Picks without a published figure are left off.

Official sites

Sources

Prices, specs and availability change; confirm on the official site before you buy.

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