There may come a time of the year that is especially busy for you, in terms of flying. December is like that for me; between holidays to see family and mileage runs to keep my elite status, the end of the year usually has several flights packed into it. In this new scenario, which shouldn’t take any extra time to comprehend, I want to quickly show you how you can save a few bucks by booking two itineraries together.

For my example, I need to fly from New York to San Francisco on the first weekend of December, followed immediately by a trip to San Juan, Puerto Rico on the weekend after. I will be flying from New York City on Friday both times, and returning on Sunday. Also, for this example, I will use Delta.com to simplify things, but mixing the tricks here with some other fare hacking tips could yield further results on the cheap side.

For most people, it doesn’t seem to come into mind that these can be combined; it looks like (and, in fact, is) two separate trips. Here is what I need:
  • NYC – SFO Nov. 30 through Dec. 2, 2012

  • NYC – SJU Dec. 7 through Dec. 9, 2012

Here is what it looks like when I do the normal thing and book each separately:

That was the San Francisco itinerary, now here’s the San Juan:

You see, the total of both flights comes out to exactly $746.

Now, what if we tried to book this as one itinerary? That would mean that we should handle this ticket as a multi-city itinerary, basically a trip from New York to San Fran for 2 nights, followed by a flight to New York for 5 nights, followed by San Juan for two nights. Get it?

Going to Delta.com’s Muti-City flight option, I input all four segments of the trip:

  1. JFK – SFO, Nov. 30, 5:00pm
  2. SFO – JFK, Dec. 2, 4:00pm
  3. JFK – SJU, Dec. 7, 8:30am
  4. SJU – JFK, Dec. 9, 5:09pm
Here is the result:

Did you see what just happened there? It was a grand total of $746.00, now it is $673.71, a savings of $72.29!

And throughout, every aspect of the search stayed the same; same flight numbers, same times, same fare class. Now, I’m not sure what exactly allows for this cheaper fare when booked together, though, by looking above, we can see that we can rule out tax savings. I had previously thought that perhaps the carrier-imposed fees would be treated all as one ticket, but that’s not the case. Whatever it is, it’s cheaper this way, so make sure you remember this simple trip the next time you have two flights in mind!

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