A single open jaw flight is an arrangement in which the return flight does not start where the the outbound leg of the flight ended, or the return leg of the flight foes not end, where the journey begun. A double open jaw flight is a flight, where the outbound leg and the inbound leg doe not have a starting or ending point in common.
An example for a single open jaw would be a flight from Frankfurt to New York, but with a return flight form Boston to Frankfurt, or a flight from Frankfurt to New York, with a return leg from new York to Munich.
A double open jaw would consist of a flight from Frankfurt to New York, but with a return flight from Boston to Munich.
The reason for an open jaw flight may come from the flight schedule. (I.e. there is no return flight from new York to Frankfurt available, or the price would be much higher.) Or the reason may come from your side. Maybe you have an appointment in New York, one in Boston, and another one in a small town between New York and Boston. In this case you would use a car or train to travel from New York to Boston, and create an open jaw flight with the return leg originating from Boston.
The task for you or your travel consultant is now to fit the different origin and destination points into one fare. The first step to find such a fare is to search for an airline, or possibly a pair of airlines sharing a common alliance, who connect all three or four airports involved in your plan.  The big alliances have at least some fares which allow a combination of their flights in one flight schedule without propelling the price through the roof.  The second step is to find a fare which allows in its rules an open jaw flight
Up to this point everything is clear cut, and with a bit knowledge about the flight schedules of the airlines, and an idea which airlines share an alliance the task should be doable. And up to this point even the booking engines manage to handle an open jaw flight.  But now comes the tricky part of the story:
Connected to each fare rule is a routing table, spelling out, which flight of which airline you can  use. This table is the tool, on which a booking engine depends. But there is another topic in the rules set, which specifies the flights which can be used in terms of flight numbers. In this rule they allow or disallow mostly code share flights, which are operated by another airline than the flight number suggests.
An example would be a fare which allows flights from KLM and Air France, which in fact belong to the same company. So we use Air France to fly from Stuttgart to Chicago, and KLM to return from Detroit to Frankfurt. We find a nicely priced flight with Air France from Stuttgart to Chicago and back, and where is also a very affordable KLM-flight from Frankfurt to Detroit. But as soon as we combine these offers to an open jaw flight the price goes up to 3000 Euro. Why? Because the inbound leg from Detroit to Frankfurt is actually flown by Northwest Airlines, although you see a KLM flight number in the schedule. But the fare rule of Air France allows only flights operated by Air France and KLM. And the rule of KLM allowing flights operated by Northwest Airlines excludes Air France flights.
The solution would be to use a return flight from Detroit via Amsterdam to Frankfurt, or better, if possible, a flight with KLM via Amsterdam to Chicago, this way retaining the direct flight from Detroit to Frankfurt.
You can try to optimisa an open jaw flight in a booking engine by trial and error, but this will take a lot of patience and frustration, because the flight numbers in a booking engine do not tell by themselves who operates the flight in question. A travel consultant with access to a global distribution system like Sabre is likely to produce better and faster results, because he has all the relevant information  at his fingertips.

If you need an open jaw flight and lack the time or patience to play with the booking engines the trial and error game, we are happy to create your flight shedule. Just send us a request for your free TailorMade TravelPlan

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