I have a long distance relationship and therefore I run into similar issues. Unlike most traveleres and therefore search machines I was looking for the dates wi

I have a long distance relationship and therefore I run into similar issues. Unlike most traveleres and therefore search machines I was looking for the dates with the cheapest flights from or to my city from or to my girlfriends city. I do not care which airline, dates or weekdays. All I care is arround the weekend and as cheap as possible. So I made a ruby script which searches all those thousands of possible combinations in a flightsearch machine, took the 20 cheapest flights per date combination, took my favourite direct flights per date combination and put it all into a basic rails application. After that I could group and rate those dates and see when I should book which flight. Also important for the rating were: total flight time, favourite airlines, hated airlines and the price difference between cheapest flight and favourite flight. Like this I could get a nice overview how my girlfriend and me can meet easily. The time spent developing exceeded the usual flight search time quite fast. As my flight search machine I used swoodoo/kayak which is in my opinion by far the best I found. /sorry for any typos in this comment, I actually just landed.:-)