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Sure, sites like Orbitz, Priceline, and Travelocity may seem like a good deal but only if you expect your trip will be without delays, changes, or weather issues. Anyone who has had any sort of dealings with the aforementioned companies' customer service departments probably has some horror stories to tell.

If you want a good deal and you have some reasonable advance notice and flexibility, your best bet is to call the airline directly. Think you're too smart and savvy to use a travel agency? Those online companies are travel agencies. They buy tickets in bulk from consolidators and sell them to you at a ridiculous profit, just like the Mom and Pop travel agency down the road. As I said before, they're great if you're travelling last minute and just need a good deal but make sure when you look at the price you're prepared to pay at least twice that if you miss your flight or get caught in weather. Most airlines have an advance purchase, seasonal, and last minute lowest-fare specials. Some fares can be hundreds lower if you're willing to stay over on a certain day. Some are weekday as opposed to weekend fares. When do the shoulder/offseason fares start and end? How many days in advance do I have to book to get the lowest fare? Is the fare going to go down in a few days? These are all questions you can't really get answered online. Go ahead and call the airline yourself and find out all you can about the fare structure. Have ideal dates in mind but be flexible. Keep in mind that saving 100 bucks by leaving three days later isn't really a deal if your hostel and beer money for those three nights is 200 dollars.