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I will use my specific situation, but this should only be considered as an example which should be applied generally. My itinerary would be as such:

London --> Austin --> Rio de Janeiro --> London

and my goal is to do this as cheaply as possibly. After receiving this epic answer I learned that my best option is to find a flight via the US that allows for some sort of 'extend stopover.' referred to as a Free Stopover. Continuing my research I found a flight on the American Airlines website for a return ticket that has two stopovers, one in each direction:

London --> Dallas --> Rio de Janeiro --> New York --> London

for a very good price. To be clear Dallas and New York are stopovers. This would be ideal since Dallas is only a three hour drive from Austin. Now, the question is, how do I book this itinerary that allows an extended stopover. In other words, I would like to land in Dallas on Monday and then take the flight to Rio the following Friday i.e. 5 days later.

I realise there are already similar questions out there (such as this one and this one), but they don't cover the specific and pragmatic issue of exactly how to book such a ticket. Obviously, I can already just buy the ticket online, but how do I change the date of the Dallas --> Rio flight?

EDIT

I should clarify, that the flight I found has two stopovers, but I only need the one in Dallas. Also, and I am not sure if I am becoming annoyingly redundant yet, but I am not looking to simply get a stopover, but to have what is termed a Free Stopover, that is being able to arrive in Dallas, but then have a flight for Rio scheduled days later, but still within the dates of my return ticket.

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there is something I do not understand: when you say "I found a flight", what do you mean? You found it on ITA software or on a regular travel agency website or somewhere else? if it's the first, I guess you should try to find the same flight through a regular travel agency(online or by phone as @Kris said or a walk-in one). Otherwise, make clearer the "I found a flight" please. –  Vince Jan 3 '13 at 16:35
    
@Vince I have edited that line. By 'found', I mean I searched for the ticket on the American Airlines website. Thanks. –  Eric Brotto Jan 3 '13 at 16:56
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3 Answers

Almost all travel websites allow you to book a "multi-city" itinerary, where you can enter multiple legs and dates for each leg.

As the trip you've listed appears to be all on American Airlines you could book it on their website (www.aa.co.uk if you're in the UK) by clicking on the "Multi-City" link on the homepage (note that on AA, this is actually a link, not a check-box like the Return and One-way options). You could also use any of the popular travel websites like Orbitz, Expedia, etc.

Most websites allow you to enter up to (at least) 6 flights and their respective dates - in your case you just have 4 (LON-DFW, DFW-GIG, GIG-NYC, NYC-LON).

On the AA site specifically, make sure that you select the "Search by Price" option, otherwise it may end up showing you more expensive flights first.

In practice, many websites Multi-City searches are fairly bad at finding you the cheapest flights - I'm not familiar enough with AA's search to know if it fits into that category, but often it's a good idea to use something like ITA Software's flight search in Multi-city mode to find the exact flights/dates that are cheapest, and then select those exact same flights on the AA website.

If you're not comfortable booking this online then you could also do it over the phone with the airline or with a travel agent, but be aware that they will most likely charge you an additional fee to do this!

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I appreciate the effort, but booking a multi-city ticket does not give me the explicit option of selecting a Free Stopover which is what I am specifically looking to do here. Otherwise my question would be a duplicate of all the others which more generally address the multi-city issue. –  Eric Brotto Jan 3 '13 at 16:00
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Just enter your flights and it will look after the stopover for you. eg, LON-DFW on March 1st, DFW-GIG on March 6th - and you've got a stopover! However many fares only allow 1 stopover and you've got 2, so that might bump you up to a higher fare class. –  Doc Jan 3 '13 at 16:55
    
Please see my edit –  Eric Brotto Jan 3 '13 at 17:01
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Since you've narrowed it down to a specific airline, the answer is simple, contact their booking department and ask them directly. They do charge a small fee for booking made via phone, but it is probably worth it if you can secure the flight at the the price you've found.

It is entirely possible that they do now allow you to do this at the price you found. They may view the stops in Dallas and New York as incidental and charge you very differently for the kind of arrangement you are looking for.

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There is an old techinque called the "Open Jaw Ticket" that would get you what you want. Imagine, for example, if you did this:

LON -> DFW (on 1/1) with a return DFW -> LON (on 1/31)

There is nothing that says you couldn't also fly

DALLAS (DFW) -> RIO (GIG) (on, say, 1/3) RIO -> DALLAS (on 1/30).

Throwing NYC into the mix makes it a little more complicated, since your interior ticket now becomes a multi-city, but you get the idea. (I think the exact nature would be LON -> NYC, with an interior of NYC->GIG, and GIG->DFW. Involves one extra leg though...)

Normally, this tactic was used when weekend layovers were required. I used to fly to Detroit every week, so I would fly IAD -> DET on Monday Week 1, with a return of Fri Week 2. For the intervening weekend, I would just have a DET -> IAD round-trip the weekend in the middle.

That said, this technique will guarantee you get the layover you want - just schedule your flights accordingly.

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