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Specifically, plane tickets usually don't get cheaper closer to the departure date. Instead, flights tend to be the most inexpensive when you book between four months and three weeks before your departure date.
As the event nears, secondary ticket sellers are more likely to lower prices so they can recoup some of their initial costs. The day before, or the day of, an event is when you'll likely to find the cheapest concert tickets. This is especially true if an artist is struggling to sell concert tickets.