Just stick some common sense into planning and ask yourself few questions like, what's the weather like (CAT I, Non-precision, Just about VFR or is a beautiful, gin clear sunny say?), what's the aircraft like (Full IFR, VFR etc.?) and what happens if something breaks (on the plane or on the airport)? Commercially, you'd pick the closest 'company' airport but privately, given a choice, maybe you'd select the one with the best alternative transport links or maybe the one with the cheapest parking. A proper plan will also allow for a one level of degradation in the aircraft (like ILS failure and a diversion to a non-precision airfield, or NDB failure and a diversion to an airfield that is VFR). Then you have to carry enough fuel to start-up, climb and fly to your destination, make an approach, go-around and divert and arrive with a reasonable amount of fuel at your alternate.
PM