Flying, it takes us about 5.5 hours from door to door, provided all goes well. This doesn't sound so bad until you consider that we must leave home no later than 2 a.m. We have about a 2 hour drive to the airport, a time change (We're in Central, and the airport is in Eastern.), and a long ways to travel between long term parking and the terminals. Ours is not the most efficient airport (and I'm being kind when I state it this way), so we must allow the full 60 minutes (prefarably more) before the stated departure time. Also, we almost always have to fly Delta (only direct flights from here to Orlando -- next best has a loooonnnnngggg layover in Atlanta), which has become not so reliable (as in we've had flights cancelled at the last minutes and long delays are expected). The plus side of flying is that we can snooze for the 2 hour flight, and we get to Orlando early (provided the flight leaves on time). If all goes smoothly, we can be at our resort by 10 am (using towncar service not a rental or DME). The negative, we've been up all night and, often, had to deal with the not-so-friendly staff at our regional airport and the Delta counter (no complaints with flight staff -- just the counter people).
When we take our children, we always drive. (This is not a cost issue, as driving now costs more than flying with cheap rates. Instead, it has more to do with flying with a 3, 5, and 13 yo on flights that are often delayed, sometimes re-routed, and occasionally cancelled. NOT FUN!!!) Not that driving 15+ hours with them is a barrel of laughts. Actually, it's not too bad after they fall asleep. Thus, we leave home in the early evening hours, drive through the night, and arrive mid-morning at our resort...if the kids sleep. Otherwise, we are constantly stopping for snacks and bathroom breaks. (If you have children, you already know this: No two children ever have to eat or go to the bathroom at the same time...or even within 10 minutes of one another.) One trip took us 21 hours!! I never thought we were going to get to WDW. Instead, I expected the entire week to pass at rest areas, gas stations, and fast food franchises. Ugh!