Hidden city ticketing with stopovers instead of layovers

Question

My understanding of terminology:

• Layover: Typically <12 hour stop, where your checked luggage are automatically transferred between flights
• Stopover: Typically >12 hour stop, where you must manually re-check your luggage between flights
• Hidden city ticketing: Booking a layover flight where your actual destination is the layover, and intentionally miss the second leg of a flight to get a cheaper fare

A commonly cited limitation of hidden city ticketing is you cannot check any bags, and it might put you in bad standing with the airline/alliance if done too often.

But I remember in the ticketing rules of many airlines, that converting layovers to stopovers are generally pretty cheap (or free!). And a stopover would let you check luggage, or even explicitly cancel the second leg if your ticket class allows it. It even prevents the airline rescheduling a different stopover point if they cancel flights.

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For example, I found the following example (LAX → HND), directly on the airline's website:

(Prices are for business:P class tickets)

The "regular" hidden city option (with a layover) is $1926 (~31%) cheaper than the direct ticket. But the layover can be converted to a stopover for a $177 premium, which still is a $1749 (~28%) savings over the direct ticket.

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Is there any reason I shouldn't book this kind of "hidden city w/stopover" ticket over a normal direct ticket?

Are there any tools that automate looking for these kinds of tickets? It seems most tools can only search for "hidden city w/layover" type tickets, and some even limit you to economy class.

(For the record, to find the above example, I first found regular economy class "hidden city w/layover" tickets on https://skiplagged.com, and then checked ITA Matrix for business class "w/stopover" versions, then confirming on the airline's website)

Answer 1

Is there any reason I shouldn't book this kind of "hidden city w/stopover" ticket over a normal direct ticket?

No. I actually think this is a great idea. People miss flights all the time for all sort of reasons and the airlines are even banking on it (by overselling capacity). I highly doubt that the airline would suspect anything intentionally here especially if you put a week or so of stopover time in. This would be much harder to detect than a missed layover where the airline knows you are already at the airport of your second leg.

Technically you would be required to pay a no-show, cancellation or repricing fee but the airline knows that this is utterly pointless and they won't bother trying to collect any money from you.

It' be interesting to see what would happen if you cancel the second leg a few days before departure. You may actually get some money or travel credit, but if you are planning on doing this repeatedly, I wouldn't push it :-)

Clarifying the terminology:

• Layover: You fly from A to C via B. It's a single segment but two flights. You check-in only once. Bags will be checked through. At B you can stay in the transit area (if applicable), so you typically don't enter the country and don't need a visa. The airline is free to re-route you through a different connection point if needed. The airline has the responsibility to deliver you to C but can choose the path. Most airlines will allow layovers of up to 24 hours (but occasionally longer).
• Stopover. You fly from A to B and then from B to C. These are two different segments. You need to check in twice and your bags are not checked through. You may be required to enter B's country and leave the transit area. The airline is required to deliver you first to B and then to C. The length of a stopover can be anywhere between "as short as you think you can make it" to "whatever the ticket allows" which is typically many months.
• Direct is not well defined (anymore). Non-stop means it's a single flight from A to B. Direct may or may not include a stop and sometimes its just a two legs having the same flight number so the airline can market a specific route as "direct".

Answer 2

The main risk of doing hidden city bookings is that your transit point is not guaranteed: the airline can theoretically reroute you via any option that gets you to your destination, and there's nothing you can do about it.

However, if you have a stopover, this risk goes away: you've paid for the right to be in the stopover city, so it's no longer hidden at all, and what you have is a multi-city booking instead.

And yes, you can skip the second leg without consequences, as long as you don't make a habit of this. However, this will invalidate any return tickets you may have, and usually booking two one-ways is much more expensive than booking a return.

If your plan is to visit multiple cities, you might want to look into open jaw tickets where the return point is from a different city, and then buy a cheap LCC fare to travel between the two.