re: Booking Flight to Rome. Best time to book?

I'm looking to do similar, looking at flying in to one side of the country and flying out of the other. No set plans yet, just trying to figure out how to best set up my alerts, should I just set up a bunch of one way alerts and see how it works out? Are there any airports/airlines that tend to be cheaper?


If it matters: leaving out of MSY. I have plenty of Chase UR & AMEX MR to book, & was thinking of doing business class if reasonable for the trans-Atlantic portion.