🏴‍☠️ Fly Smarter with ChatGPT

✈️ Flights You’ll Brag About

Author

Captain YAR
April 22, 2025 • Estimated Reading Time: 8 minutes

A few years ago, I booked a last-minute trip without thinking twice.

Same airline I always used. Same route. But the ticket?

It was three times the usual price, and somehow still landed me between two armrest-hogging strangers in the back row. That was the moment I realized: people who don’t know the hacks are playing a rigged game.

Let me share with you seven prompts that could help you get the best deals (work better with a new 04-mini model with “Search” turned on).

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🔍 Flight Deal Hunter: Why You’re Probably Overpaying Without Even Knowing It

Let’s say you’re flying from LA to Tokyo this July.
Most folks plug in their dates, pick the cheapest round-trip, and call it a day. But that’s like buying a used car without checking the mileage.

Here’s a prompt on how to hack it:

“I’m flying from [CITY A] to [CITY B] on [DATES]. Provide three concrete cost‑cutting tactics—such as choosing alternative nearby airports, employing hidden‑city ticketing, or shifting to off‑peak departure/return dates—and estimate the potential savings for each.”

🚨 Mistake-Fare Finder: These Deals Weren’t Supposed to Happen

Some fares slip through the cracks, like a $249 round-trip to Europe. When they do, you gotta be faster than the algorithm.

Latest examples:

  • NYC → Lisbon for $249 (TAP Air Portugal)

  • Toronto → Tokyo for $312 (Air Canada)

  • Paris → NYC for $198 (Norse Atlantic)

How to snipe them:

  1. Set up alerts using FareDrop or Secret Flying.

  2. Book directly through the airline or via Google Flights, fastest wins.

  3. Don’t call the airline. Just book and pray it sticks.

“Act as an airfare hacker: identify two or three recently leaked mistake fares originating in [COUNTRY or REGION], including airline, route, and price. For each, outline step‑by‑step booking instructions to secure the fare before it’s corrected.”

🌍 Low-Cost Destination Recommender: Big Experience, Low Spend

Traveling in October with a $700 budget?
Skip the tourist traps. Try this instead:

“For travel in [MONTH] with a total budget of $[X], recommend five under‑the‑radar destinations. For each, give (a) average round‑trip airfare, (b) primary cost drivers, and (c) one or two local highlights that maximize value.”

Track the best deals using Hopper or Kiwi.com.

🧠 Price Prediction Assistant: Book Smarter Than Everyone Else

You’re watching prices for Chicago → Barcelona in August and don’t want to overpay.

Here’s your move:

“I’m tracking fares on [ROUTE + DATES]. Analyze historical pricing trends and current market data to pinpoint the exact calendar dates when ticket prices are lowest. Also, recommend two fare‑alert tools or strategies to monitor ongoing fluctuations.”

Waiting too long = regret. Set a deadline.

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🛫 Alternate Airport Strategist: Fly Out Smarter, Not Harder

Flying from San Francisco to Rome? Don’t just look at SFO and FCO.

Better bets:

  • Near SF: Try Oakland, San Jose, or Sacramento

    • Differences? Up to $250 less, depending on time

    • Use Rome2Rio for transfer options

  • Near Rome: Naples, Pisa, Bologna

    • You might land a much better price, and a prettier train ride

“Compare flight costs for departures/arrivals at airports within [X mi/km] of [CITY A] and [CITY B]. List three alternative airports per city, the difference in round‑trip airfare versus the main airport, and typical ground‑transport options (and costs) to reach them.”

🪙 Cash + Points Optimizer: Stretch What You’ve Already Got

Got 65,000 Chase points and a $300 budget to fly NYC → Lisbon?

Try this:

  • Transfer points to United or Air Canada using Point.me

  • Find a saver award for 45,000 miles

  • Use the rest for a night in town or a better seat

“I have [XX] loyalty points with [PROGRAM] and a cash budget of $[Y]. Devise the most cost‑efficient cash + points itinerary from [CITY A] to [CITY B], showing (a) points + cash breakdown, (b) effective cents‑per‑point value, and (c) booking steps.”

💼 Luxury for Less Finder: Fly Business Without Paying Business

You want that lie-flat seat to Bali but don’t want to burn your entire year.

Here’s how to upgrade the game:

  • Use upgrade auctions on airlines like Lufthansa or Air New Zealand

  • Book off-peak legs—Tuesdays and Saturdays rule

  • Try smaller carriers like ZIPAIR or Bamboo Airways with ultra-competitive pricing

“I want to fly business class to [DESTINATION] for under $[X]. Provide three realistic upgrade hacks—such as bidding on upgrade auctions, choosing low‑demand flight times, or leveraging smaller carriers—and include detailed instructions for each.”

Use SeatSpy or ExpertFlyer to track upgrades opening up.

🧭 Don’t just travel. Outsmart the whole system.

The real flex isn’t spending big. It’s knowing what others don’t.
Re-read this next time you book anything. You’ll never go back.

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