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A friend of mine booked a flight, via aa.com, to London on September 13. AA6236, operated by British Airways. They're traveling to Paris, via train, to Naples, via an expedia.com booked flight and then to Rome via train. They're then flying out of Rome on September 23 via AA721 (FCO->CLT) and AA2577 (CLT->AUS). Total flight time for the return trip: 15h 20m. They paid $1,208.96.

I'm now trying to book a similar flight. I want to fly into Naples on September 18, meet my friend and then fly out of Rome with them on September 23. Only problem: I'm not being presented with the same return trip flight options that they had.

For $1,623.66 I can purchase a multi-city flight that flies out of Rome on September 23 via AA6751 (FCO->LHR) and AA6237 (LHR->AUS). Total flight time for the return trip: 32h 10m. The return flight is totally different.

For $3,106.66 I can purchase a multi-city flight that flies out of Rome on September 23 via AA111 (FCO->ORD) and AA2995 (ORD->AUS). Total flight time: 15h 32m. The flight time of the return trip is much better but the cost is a lot more. A lot of the appeal of my friends booking is that it was both cheap and (relatively) fast.

I just don't understand why I'm not being presented with the same options.

I was just able to get ITA Matrix to price out the exact itinerary you want, but it also costs $3,103.66:

(There are a couple of different ways to get to Naples with this, but most are similar in price.)

The reason for the fare difference appears to be the difference in availability in fare classes. Your friend's itinerary can be booked in fare classes N and V, which American uses for some of its cheaper economy fares. The flights to Naples are pricing out in H class, some of their more expensive economy fares.

Sadly, a one-way flight from Rome to Austin on your friend's itinerary is pricing at $2,246. I was thinking you might do that and then grab a $600 Condor flight from Austin to Naples, but you'd still be coming in at around $3K that way.

If you're able to fly out on the 16th instead, you could do this for about $1,300, but note the change of airport in London:

I just don't understand why I'm not being presented with the same options.

The simple answer is that the fare buckets for the itinerary that your friend has purchased may have been exhausted by the time you started your searches - there are only so many fares available in given classes for given routings.

There is also the airlines own yield management tactics to consider. Airline pricing and routing management is complex, and if the airline wants to improve a particular route yield (either the revenue generated by that route or the passenger count on that route, depending on the metric the airline is using at the time) then they will simply not offer alternatives in order to push you onto a given routing.

The only thing to suggest at this point is to actually call American Airlines and speak to one of their booking agents, explain the situation and ask them if they can put you on a specific routing. You may be in luck and they may simply have the routing blocked out in the automated ticketing system, but available to the booking agents.

Or the route may be sold out.