From our experience in dealing with airlines the most inexpensive tickets are those that booked way in advance. We usually book ours if we can at least 8 months out. Flights are also cheaper when booked for flying in or out on Tuesday through Thursday. Flights are always higher around spring break and the holidays (Thanksgiving and Christmas). Hope this helps. Sometimes if you call reservations for a specific airline and ask when are tickets the most reasonable they will a lot of times be happy to tell you.
I agree, farther in advance, espically if traveling during high times such as student breaks and holidays. If you want to go in an off time, then sometimes its best to wait until about 4 months out.
For high demand periods like Thanksgiving, it is usually best to book at IPO, that is typically 331 days in advance, notably somewhat less and unpredictable for Southwest.
For other periods it is usually better to wait for a fare war instead of book at the everyday low price. For Southwest you can subscribe to their Ding program and hope that an Orlando offer comes your way soon.
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