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Travel

Trips, bookings and getting around · 176 ideas

Plan my Montreal trip: Airbnb, direct flight and an itinerary that dodges construction

By voice, Simmons asked László for an October 15–18 Montreal trip: a central, inexpensive Airbnb, the cheapest direct flight with an aisle seat, and a plan of things to do. The Dot compared stays, caught repeated complaints about a squeaky Murphy bed at a 4.75-star listing, filled in his flight details from his travel records, rerouted the Mont Royal walk because the cross was under construction, and stopped at checkout for him to pay.

TravelWent wrong

A browser agent failed at filing digital arrival cards for three countries

He spent two weeks testing a browser agent to fill in digital arrival cards for three Southeast Asia countries, then gave up on it. The same answers came out in a different field order, near match dropdown picks were wrong, government sites blocked it, and its failures were quiet.

This one went wrong. See what happened before you try it.

Complain to the hotel until they refund me

A commenter says he feeds the AI his booking details and complaint and lets it negotiate petty corporate disputes. For a Milan hotel stay, the AI first won a free night he rejected, then a 25% reimbursement he accepted.

Turned her saved Instagram posts into a 4-day Barcelona and Mallorca itinerary

Creator Chanelle Howell connected the AI to her Instagram saved folders; in about 45 seconds it generated a 4-day Barcelona & Mallorca itinerary from her aesthetic preferences, shown as a phone webpage with Day 1 in Barcelona's Gothic Quarter, specific restaurants (Los Caracoles, churros at Masia de Sabor, Tapeo), clickable links, opening hours, and booking options.

TravelPartly worked

Reached Delta's Confirm & Submit screen for a $250 flight-delay claim in

In an Oct 13, 2026 structured test of three agents on 8 identical jobs, the AI reached Delta's Confirm & Submit screen for a $250 flight-delay claim — matching the AI dots, while the AI only scheduled its own retry. The test used a made-up family and nothing was actually submitted.

$250
This only partly worked. Worth knowing before you try it.

Move my rental-car pickup to Charlotte after my flight falls apart

Jared Lee was flying to New Bern, North Carolina, where his father may be dying, when delays at lunch told him he would miss his connection. His rental car was booked for New Bern airport. From the taco restaurant, he asked the AI to change the rental to a Charlotte pickup for the 4.5-hour drive. A couple of text messages later it was done: new rental, new confirmation. He estimates it saved him at least an hour of hold time, spent instead present with his wife.

Turn my Europe trip notes into live routes in Google Maps

FlipIt's account of Business Insider's reporting describes UX designer Jay Eskenazi feeding his own compiled notes and recommendations into AI during a three-week Europe trip. The AI mapped his points of interest and exported routes into Google Maps, updated afternoon itineraries as plans shifted — accounting for opening hours, ticket availability and real-time events — and surfaced Barcelona festival information not yet fully published in English.

Find the refund hiding in my inbox

After SAS cancelled and rebooked his family's Oslo flight and a human agent said the dropped prepaid meal fees couldn't be fixed, a father asked the AI to pursue the reimbursement he had never filed since July. The AI searched all his SAS emails and found the airline had already reimbursed the fees the day of the change - buried under that day's notification spam.

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Every idea is a real post from someone who tried it, summarized in our words, with a link to the original. App names are swapped for plain words.