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Tish Talks AI
Chapter 02 — AI for Travel

Plan better trips without the overwhelm.

Award travel, itineraries, hotels, flights, family trips — AI takes the research off your plate so you can actually enjoy the adventure.

Trip planningAward travelHotelsFlightsPackingCruisesFamily travelItineraries
PASSPORT
UNITED STATES
OF AMERICA
FROM
JFK
→
CDG
22 JUL 25
PASSENGER
JENKINS / TISH
CLASS
ECO
FLIGHT
TK 0241
GATE
B14
SEAT
14A · WIN
RUE DE RIVOLI
ENTRY / EXIT STAMPS
ENTRYFRANCE · CDG
ENTRYJAPAN · NRT
ENTRYMEXICO · CUN
ENTRYUK · LHR
Paris · Jul 22
→ Louvre 9am
→ Café lunch
→ Eiffel 5pm
→ Seine cruise
CDG
PARIS
CHECKED
LUGGAGE
PRIORITY
ADMITTED · CDG · FRANCEENTRY22 JUL 2025
Featured Story
A boarding pass and passport in front of a changing airport departure board, representing the uncertainty of deciding when to book travel.
Travel· 5 min read

Should I Book It Now... or wait?

Travel prices change constantly, but nobody can reliably predict what they'll do next. Here's how I use AI to think through booking decisions without falling into an endless cycle of refreshing prices.

Prompts

Prompts to Try

Copy and paste these exact prompts. Just fill in your own details in the brackets.

Trip planning

Trip Itinerary Builder

I'm planning a [X]-day trip to [destination] for [number of people]. We like [type of activities — culture, food, adventure, relaxation]. Our budget is approximately $[amount] per day. Build me a day-by-day itinerary with specific suggestions, including when to book in advance.
Tip:Paste this into ChatGPT or Claude and then ask follow-up questions to refine it.
Award travel

Award Flight Research

I want to fly [route] in [cabin class] using points or miles. I have [X] points in [program]. Walk me through my best options for transferring or using these points, including which airline partners to look at and what redemption rates to expect.
Packing

Packing List Generator

Help me create a packing list for a [X]-day trip to [destination] in [season/month]. I'll be doing [activities]. I prefer to [carry-on only / check a bag]. I tend to overpack [category] — keep me honest.
Hotels

Hotel vs. Points Comparison

I'm deciding whether to pay cash or use points for a hotel stay. The hotel costs $[nightly rate] per night for [X] nights. I have [X points] in [program]. Help me calculate the cents-per-point value and whether redeeming makes sense.
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More on AI for Travel

Elegant hotel lobby representing the challenge of choosing the right hotel before booking.
Travel
6 min

Every Hotel Looked Great Until I Read the Reviews

Hotel reviews can be overwhelming, contradictory, and sometimes misleading. Here's how I use AI to identify recurring patterns, separate one-off complaints from real issues, and book with more confidence.

Read article→
An open suitcase surrounded by receipts, baggage tags, transit cards, attraction tickets, and other small travel expenses that can add up during a vacation.
Travel
5 min

I Budgeted for the Flight and Hotel—Then Everything Else Happened

Flights and hotels are only part of what a trip really costs. Here’s how I use AI to uncover forgotten travel expenses, build realistic budget scenarios, and enjoy the trip without quietly going into debt.

Read article→
A busy modern airport terminal at sunset with travelers walking through a spacious concourse pulling rolling luggage. Floor-to-ceiling windows overlook airplanes on the tarmac as warm golden light reflects across the polished floors, creating a cinematic atmosphere of travel, movement, and anticipation.
Travel
7 min

Do I Really Need Travel Insurance?

Travel insurance isn't always a simple yes-or-no decision. Here's how I use AI to compare financial risk, refundable bookings, and my credit card's travel protections before paying for extra coverage.

Read article→
Tools

Recommended Tools

The tools I actually use for these tasks.

ChatGPT

Freemium

AI Assistant

The most widely used AI assistant. Great for thinking through problems, drafting, and brainstorming.

Tish's Take

"My daily driver. Not perfect but the best all-around starting point for most real-life tasks."

Perplexity AI

Freemium

AI Search

AI-powered search that cites its sources. Great for research where you need to verify information.

Tish's Take

"Use this when you need real sources, not just AI confidence. Especially good for financial and travel research."

Google Gemini

Freemium

AI Assistant

Google's AI assistant, deeply integrated with Google Workspace and search.

Tish's Take

"Most useful if you're already in the Google ecosystem. The Workspace integration is genuinely useful for docs and sheets."

KAYAK AI

Free

Travel

Travel search with AI-powered trip recommendations and price tracking.

Tish's Take

"Good for getting a starting point on flights and hotels. Use in combination with AI chat for deeper strategy."

Downloads

Downloads & Toolkits

toolkit

AI Travel Planner

A step-by-step AI workflow for planning any trip — from first idea to booked itinerary — using free AI tools.