Everything about the flight that isn't the ticket price
Which airline actually flies the route, how long a connection really needs at that specific airport, what your bag will cost, and where the lounge is once you are through security. Grouped by when you will need it — working out the route, before you leave home, and at the airport itself.
Working out the route
Before pricing anything, find out whether a nonstop even exists. These are the full published networks for the three US carriers, plus who flies what worldwide.
Which programme is worth it for the way you actually travel, what each costs, and how long approval takes.
At the airport
Connection times that reflect the airport rather than the airline's minimum, where the lounges are, and what to do with bags between checkout and departure.