If you're looking for flights originating in the US, head directly to www.kayak.com. They search all of the discount sites, as well as the airlines' sites, simultaneously, and give you all the information up front - prices, taxes, times, multiple ticketing sources for the same flight (listed by price). They even mark the flights that frequently run late. Kayak is not a ticketing agency, just an informational website, so clicking a link will take you to the ticket-selling website.
If you're looking for flights that originate outside of the US, get yourself to www.skyscanner.net. Like Kayak, they don't sell the tickets, just tell you where to buy them most cheaply. Amuse yourself for hours with their drop-down menu and maps!
If you are flying into one city but out of another, compare the cost of ground transport to an open-jaw ticket - for example, flying into Paris and out of Madrid, rather than taking a pricey train back to Paris from Spain at the end of your trip.
If you are headed off to Europe from the US, consider: there are many cheap inter-Europe hopper flights to be had (especially if you buy well in advance); you might find it cheaper (and more interesting) to fly into a city that is not your ultimate destination and take hopper flights around. Last summer I was meeting a friend in the Netherlands and travelling to Germany. A flight into either Amsterdam or Berlin cost over $900, and an open-jaw ticket cost even more. However, I found a round-trip ticket to Dublin for just over $400, and hopper flights from Dublin to Amsterdam, and Berlin back to Dublin, for under $125 altogether. Score! I spent a day in Ireland at either end, and got to see some excellent museums (http://www.museum.ie/en/homepage.aspx) and an ancient archaeological site (http://www.knowth.com/newgrange.htm). Just be sure to leave yourself enough time between flights, and check out hostel/hotel prices and availability if you're going during a busy time.
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