Whenever I see tools like this, I have to point out Flightfox - http://www.flightfox.com http://www.flightfox.com. If you're thinking of booking a trip that co

Whenever I see tools like this, I have to point out Flightfox - http://www.flightfox.com http://www.flightfox.com. If you're thinking of booking a trip that could run on the expensive side, there's no doubt in my mind that experts will do better than any single tool out there (or yourself) ever could... you'll pay a small fee to run a contest, but you'll still likely absorb that cost in savings. Do yourself a favor and run a contest. Even better, spend some time trying to find the lowest price you can, then pay the $40+ to watch a few experts demolish your travel-planning skills. Often times they'll find miles hacking / loopholes / etc. that only a human could put together. The various experts behind that site are ridiculously good at getting you deals. The more complex and "open" your trip, the more space they have to save you money.