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Wait until 3-4 months before your flight to book
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In general the experts recommend buying your tickets "in advance" which usually means at least 14-21 days before your flight in order to meet the advance purchase restrictions of most discounted tickets.
For major holidays when flights tend to sell out, you'll want to start looking at fares at least several months ahead of time.
When you see a great bargain flight for your planned dates, grab it quickly since seats are usually limited.
But what if you are planning a trip very far in advance, not during a holiday season? You are best off waiting until about 3-4 months before your domestic trip (4-6 months before an international flight) to book since this is when airlines tend to start discounting their fares. Before that you're probably paying "regular price" which means too much!
If you can score a discount of 20% this way off of a $400 regular fare, on two flights a year, that's $160 in savings!