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Ask Jack: Expert advice. Plane and simple. 🤝

Real advice from our Navigators to sense-check the price, compare routes, and allow you to book with confidence.

What's included when you Ask Jack?

  • A personalised Escape Plan for your trip

  • Expert price and timing advice

  • Smarter route and airport options you might not find yourself

  • One-to-one guidance from an experienced Navigator

  • Personalized suggestions based on your trip

  • Honest, independent (unbiased) recommendations

  • A personalised Escape Plan for your trip

  • Expert price and timing advice

  • Smarter route and airport options you might not find yourself

  • One-to-one guidance from an experienced Navigator

  • Personalized suggestions based on your trip

  • Honest, independent (unbiased) recommendations

Ask Jack
Escape Plan $99 per trip
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  • Price Advice - be confident you're not overpaying
  • Flight Intelligence - get deeper insights on routes, price history and predictions
  • Direct line to our expert Navigators + a customized Escape Plan
  • Personalized suggestions for your destination

By signing up, you're agreeing to our privacy policy and terms and receiving deal alerts and travel related inspiration by email. This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Who is Ask Jack best for?

Planning one specific trip and want a second opinion before you book?

It’s perfect if:

- It’s a big spend, and you don’t want to mess it up
- Two options look similar and you’re unsure
- You just want peace of mind before you hit “book”

(We’ll reply by email with your personalized Escape Plan. )

How it works

Submit your trip details

The route, the dates, the price you’ve spotted — or just the idea in your head.

We build your Escape Plan

Our Navigators analyse the routes, pricing patterns and timing, then package everything into clear, honest advice.

You book with confidence

No overthinking. No 17 tabs open. Just clarity on what to do next

What's included when you Ask Jack?

  • A personalised Escape Plan for your trip

  • Expert price and timing advice

  • Smarter route and airport options you might not find yourself

  • One-to-one guidance from an experienced Navigator

  • Personalized suggestions based on your trip

  • Honest, independent (unbiased) recommendations

  • A personalised Escape Plan for your trip

  • Expert price and timing advice

  • Smarter route and airport options you might not find yourself

  • One-to-one guidance from an experienced Navigator

  • Personalized suggestions based on your trip

  • Honest, independent (unbiased) recommendations

Ask Jack
Escape Plan $99 per trip
Hide info
  • Price Advice - be confident you're not overpaying
  • Flight Intelligence - get deeper insights on routes, price history and predictions
  • Direct line to our expert Navigators + a customized Escape Plan
  • Personalized suggestions for your destination

By signing up, you're agreeing to our privacy policy and terms and receiving deal alerts and travel related inspiration by email. This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Payments & security

This website uses a 256-bit encrypted connection and secure payment processors Stripe and PayPal as trusted by companies like Facebook, Kickstarter, and Unicef. Your payment information will never be stored on our website.

Is this just AI in disguise?

Nope. You’ll hear from a real, flight-obsessed human Navigator. The same people who spend all day hunting down the best fares.

Do you actually book the flights for me?

We send you a personalized Escape Plan with the best routes, price context, and booking links so you can book confidently yourself.

What if I’m overthinking it?

That’s kind of the point. Send your plans to us. We’ll tell you if it’s a great deal, a “meh” deal, or a please-don’t-do-that deal — and point you toward something better if we can.

What do I actually receive?

You’ll receive a personalized PDF Escape Plan tailored to your trip. It breaks down your price, route and timing, and includes smarter alternatives if there’s a better move — all in one clear, easy-to-follow recommendation.

How fast will you reply?

We’ll be in touch within 24–48 hours to let you know we’re on it. Your Escape Plan normally lands within 5–7 days, once we’ve done the proper digging.

Is this part of Takeoff?

Not by default — but you can add an Escape Plan as a one-off. If you have a First Class membership, it’s already included.

What if you tell me not to book?

Then you’ve probably just saved yourself money. We’ll always tell you what we’d do if it were our own trip.