I need to buy a ticket to San Jose, Costa Rica on September 2 from Philaadelphia, and it's got me wondering about the best way to maximize my travel dollars. My question is, in the long term, is it cheapest to always book the flight with the lowest price (baggage etc considered), or to pay a bit more to stay loyal and accrue points? How would I even go about calculating that?
For an example, from my searches I found JetBlue the cheapest with 1 checked bag at $265, but United, who I have flown a couple times with, is priced at $358.