I have had the opposite effect. The earlier I book the cheaper the fare. The past 6 trips I book as soon as American Airlines opens those dates. The last 4 times I was able to upgrade to first class for about $200 per person. Understand I go Saturday to Saturday because of my job. So I was paying about $700 PP for coach and then upgrade as I said. Having said that, it does not appear that is working out for me this time. Looking at May '20 I am seeing coach at $850 and first class at $1,250. These are direct flights from CLT to STT. I could cut the cost a bit if I want to leave my house at 5am and go through Miami. But I like that direct flight to STT and in most cases we get in a bit early. Once I retire I can then play with the dates and hopefully do much better.