Most flight search engines now let you set up alerts to track prices, but I also think those aren't ideal because if you're flexible about where or when you might travel you'd have to set up thousands of alerts. (example: I'd like to go somewhere warm for a weekend in January from New York. There are 113 warm weather destinations within 4 hours of New York; I can leave on Friday or Saturday and return on Sunday or Monday; there are four weekends in January = 1808 alerts to set!).
This is exactly why we built Hitlist (hitlistapp.com, available for iOS and Android), an app which monitors airfares across swathes of destinations and dates and sends you notifications when there are ridiculous fares. Some of you might find it useful!