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How to Have AI Plan a Trip End to End: Plan, Book, Keep Track

Published by 3Gen Internet Corporation, maker of OpenAssistant, Skej and AGNT. Comparisons use public documentation, without hands-on testing.

A folded travel map linking a paper airplane, miniature hotel key, suitcase and calendar itinerary, with confirmation envelopes and a check-mark completion tile.

The steps below are taken from each vendor’s help pages. We have not run them.

To have AI plan a trip end to end, split it into three jobs: plan the trip, book it, and keep the bookings in one place while you travel. OpenAssistant is an option for starting the plan, since you can hand it the research by email, text or its dashboard, and its site says it books travel on the web. Pair it with TripIt to keep every confirmation in one itinerary.

No single AI tool documents all three jobs today. This guide shows which tool covers which job, with the steps from each vendor’s own docs:

The short answer

Among the tools covered here, Google AI Mode is the only one whose help docs describe booking a hotel from inside the AI conversation, and only in the US. Flights end on the airline’s or travel site’s own page in every one whose booking steps are documented. Some other travel plugins in ChatGPT’s directory say they book in chat; this guide does not cover those. OpenAssistant’s site says its assistant browses websites to book travel, and its help center covers the trip around the booking, so those are the steps shown.

Option 1: OpenAssistant (research, calendar and reminders around the trip)

OpenAssistant is an AI assistant you reach by email, text, WhatsApp or its web dashboard. (OpenAssistant) Its homepage says it “browses websites on your behalf to book travel, make reservations.” (OpenAssistant) Its help center does not walk through a booking, and Google’s hotel booking in AI Mode (below) is the better-documented route for that step. The Starter plan is free, with 1,000 credits at signup plus 100 bonus credits a day once those are used up, up to 1,000 a month. (OpenAssistant pricing) Here is what the help docs cover for a trip:

  1. Tell it your travel habits once. Add them under Instructions (app.openassistant.us/instructions). OpenAssistant’s own example is “I prefer window seats when traveling.” (OpenAssistant)
  2. Hand it the research as a task. In the dashboard, open the In-Progress tab and click New Task, or email your assistant. Say what you want back and in what format, for example a day-by-day plan as a document emailed to you and your travel partner. (OpenAssistant)
  3. Use maps for timing. Google Maps is available to every OpenAssistant assistant for travel times and nearby venues. (OpenAssistant)
  4. Put it on your calendar. Calendar permission is required in onboarding and lets the assistant view, change and create events. (OpenAssistant)
  5. Set a recurring travel summary. OpenAssistant’s example recurring workflow: “At the end of each month, send me a summary of my upcoming travel.” (OpenAssistant)

Option 2: Google AI Mode (plan, then book a hotel)

Build the plan in Canvas

Canvas is a side panel in AI Mode that holds a plan you can keep editing. Google’s help page says it’s available in English to users in the US on desktop and mobile, but its steps are written for a computer. (Google)

  1. Go to google.com/ai on desktop, or go to www.google.com and click AI Mode in the search bar.
  2. In the Ask anything bar, click the menu and select Canvas.
  3. Describe the trip. Google’s example: “Plan me a summer vacation to Florida with two kids.”
  4. The plan appears on the right. Refine it with follow-ups, or highlight part of it and pick Ask about this.
  5. Use Share to send it to the people you’re traveling with.
  6. To come back later, open AI Mode history and pick the Canvas thread.

(Google)

Google notes it is updating its Search settings, so what you see may not match the help page exactly. (Google)

Book the hotel in AI Mode

This is a real booking, paid with Google Pay. Requirements: US, English, select properties only, signed in, 18 or older, a Google Pay payment method and a US billing address. (Google)

  1. In AI Mode, ask for hotels with your city and dates.
  2. Pick a property and check the dates and number of guests.
  3. Select Continue on Google. If you see Visit site instead, that hotel can’t be booked in AI Mode.
  4. Choose a room type and rate, then enter the guest name and phone number.
  5. Select Go to Payment and confirm with Google Pay.
  6. Save the confirmation number shown in AI Mode. The booking partner also emails a confirmation.

(Google)

Limits Google lists: you can’t add children to the booking in AI Mode, and there are no promo codes, loyalty points or numbers. Google asks you to make one booking per conversation. Changes and cancellations go through the partner, not Google. (Google)

Flights: find and track, then book elsewhere

Google’s August 2026 announcement says AI Mode shows flight options, but you buy tickets through the airline’s site or a booking site. You can ask it to track prices and get an email when they change. Price tracking covers 180+ countries and territories, but not the EEA. (Google blog)

The Gemini app can search flights and hotels too, but Google says it can’t book them, change reservations or check you in. (Google)

Option 3: ChatGPT with travel plugins (search here, book there)

ChatGPT’s “apps” now live under Plugins. The travel category includes Expedia, Booking.com, Skyscanner, Trip.com and others. (ChatGPT plugin directory, OpenAI)

  1. Open Plugins in the sidebar, or go to Settings > Plugins.
  2. Select a plugin, such as Expedia, and read its requirements.
  3. Select Install plugin.
  4. If asked, select Connect and sign in to your account with that provider.
  5. In a chat, ChatGPT uses the plugin when it’s relevant. You can also call it with @, or pick it from the + menu.

(OpenAI)

What happens at booking time. Expedia’s plugin page says you continue on Expedia to book. Booking.com’s says to tap “View on Booking.com” to book. (Expedia plugin, Booking.com plugin) So ChatGPT plans and compares, and the travel site takes the booking. Both plugin pages warn that connecting may share relevant chats and memories with the app.

If you want ChatGPT to click through a booking itself, that’s the cloud browser in ChatGPT Work, on paid plans other than Go. It asks you to confirm before “confirming a booking or making a payment,” and some sites block it. (OpenAI) See our guide to ChatGPT errands for those steps.

After you install your first travel plugin, open Settings > Plugins > Permissions and choose Always ask. OpenAI says this overall setting can appear only after you install a plugin that includes an app. (OpenAI)

Option 4: TripIt (keep every booking in one itinerary)

TripIt doesn’t book anything. It turns your confirmation emails into one itinerary, which is the part of “end to end” the AI tools above don’t do.

  1. Open a free account on the TripIt website or app. (TripIt)
  2. Forward each confirmation email to plans@tripit.com. TripIt emails back when it creates the trip or adds the plan. (TripIt)
  3. Or turn on Inbox Sync so it finds confirmations itself. In the app: Account, your name, the email address, then the Inbox Sync toggle. On the website: profile icon, Account, Profile, the email, then Activate Inbox Sync. Supported: Gmail, Google Workspace, Outlook, Microsoft 365, Hotmail and Yahoo. TripIt says import isn’t immediate (allow up to 24 hours) and it looks at travel emails from the last 7 days. (TripIt)

TripIt reads only original emails from the travel company, and only the first attachment. If you forward from Outlook and it fails, TripIt suggests plain text or forwarding as an attachment. (TripIt)

Who does what

Job OpenAssistant Google AI Mode ChatGPT + plugins TripIt
Build a day-by-day plan Yes, as a task Yes, Canvas (US, English) Yes, in chat No
Book a hotel inside the tool Its site says it books on the web Yes, select properties (US) No, finishes on partner site (cloud browser can try) No
Book flights inside the tool Its site says it books on the web No, links out No, finishes on partner site No
Track flight prices Not stated Yes (not EEA) Monitoring tasks, not fare-specific in docs Fare drop alerts on booked flights (Pro)
One itinerary of all bookings Not stated No No Yes

(Sources linked in each section)

Check it yourself

This section is advice for you. We have not run these checks.

Use one trip brief in every tool: “Two adults, New York to Lisbon, 5 nights in May, mid-range hotel near the old town, one day trip to Sintra, budget $3,000 total.”

What a good result looks like:

  1. The plan respects dates, budget and the Sintra day.
  2. Every hotel and flight it names exists and is bookable on those dates.
  3. It stops and asks before any payment.
  4. You end with one place that lists every confirmation.

FAQ

Can AI book my whole trip for me?

Not from one tool, according to the docs. Google AI Mode documents booking a hotel inside the conversation (US only), and flights end on the airline’s or a travel site’s page. OpenAssistant’s site says it browses websites to book travel on your behalf.

How do I keep all my bookings in one place?

Use TripIt. Forward each confirmation email to plans@tripit.com or turn on Inbox Sync, and TripIt builds one itinerary.

What can OpenAssistant do for a trip?

Per its help center, you can store travel habits under Instructions, hand it the research as a task, use Google Maps for travel times and nearby venues, put the trip on your calendar and set a recurring travel summary.

Can ChatGPT book a hotel or flight?

With the Expedia or Booking.com plugin, ChatGPT searches and compares, and you finish on the travel site. The cloud browser in ChatGPT Work can try a booking and asks you to confirm before confirming a booking or making a payment.

Does Google AI Mode book flights?

No. Google’s announcement says AI Mode shows flight options, and you buy through the airline’s site or a booking site. You can ask it to track prices.

Try OpenAssistant

To hand off trip research and keep it tied to your calendar and email, Try OpenAssistant. Save your travel habits under Instructions first, then send it a trip brief. Plans are on the pricing page.

Sources