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In 2022, my son was flying home the day after Christmas. He is stationed in Biloxi MS, and flew out of New Orleans with a connection in Atlanta and then a connecting flight to Cleveland. 

However, once he got to Atlanta, they canceled the flight to Cleveland and said they could not get him home for about 4 or 5 days. I got the news around 6:00pm that evening and told him I would be in Atlanta in 10 hours to pick him up.  My oldest daughter went with me to break up the driving and we got there at about 4 in the morning, grabbed him and his luggage and then drove back home. We got home around 2:30 pm that afternoon. It is about 690 miles one way, so I think we drove close to 1400 miles in about 21 hours.

My son had teamed up with a Navy guy who was on the same flight and shared a hotel room. But instead of getting some sleep, they decided to drink beer and play video games most of the night. Therefore, he was less than worthless in sharing the driving home. 

Needless to say, I was pretty wiped out when we got home. 

Once you get over the 3 hour drive length these days I fly.  Hard to believe I use to drive from Phoenix to Cincinnati in a single drive, stopping only for gas & food.

You fly over a three hour drive length?  Do you live in the terminal?  For a drive that short I can't imagine that flying even saves any time unless you own your own plane.  

An example for me, my wife and I drove to Chicago for the B1G Basketball Tournament back in 2015.  Per google the United Center is 351 miles from my driveway and takes 5:24 to drive.  A flight is 1:30 direct from Cleveland or 3:15+ with connections and starts at $249*.  

I wouldn't even consider flying that.  For one thing the flight barely saves you any time.  Even with a direct flight at 1:30 it only saves four hours but I'd immediately give  half of that back in time spent driving to the airport, parking at the airport, walking to the airport, getting through security, and waiting.  When I get there, I already have my car and my luggage is in it.  If you fly you get there and need to retrieve your luggage then find a rental car then get to it, then get going.  

A second factor is cost as it is obviously cheaper to drive since even if I was travelling alone in a gas-guzzling Suburban at 15 MPG it would only take me 47 gallons of gas to get to Chicago and back.  It is marginally cheaper to drive even for one person driving almost the least fuel efficient vehicle possible.  Adding people obviously makes driving a MUCH better deal since the cost of driving doesn't change much until you get to the point that you can't all fit in one car.  Then, if you need a car at your destination the price of flying goes up even more since you have to rent one but the cost of driving remains constant since you bring your own car and don't need to rent.  

The biggest factors, to me, are convenience and flexibility.  When my wife and I went to Chicago we left after work on Wednesday and ended up staying later than expected on Sunday before driving home.  You can't change plans when you fly and you are stuck with the times the airlines offer.  You can't just leave when you are ready.  We actually met up with @nuwildcat at one of Chicago's pizza places Wednesday night.  The flight that is available leaves CLE at 7:09 and gets to ORD at 7:40 (you pick up an hour due to EST/CST).  If we left at 5pm and drove we'd get to Chicago at 9:40.  

*That "starts at $249" is laughable.  That is only if you have no luggage, are willing to depart in the middle of the night, and don't mind sitting on the wing.  If I made a similar trip for Wednesday, April 24 to Sunday, April 28 it would cost $264 per person to fly economy.  If you want to bring a suitcase it adds $80.  If you want in the "main cabin" (apparently economy is on the wing or something?) that adds $60.  If you want "Main Select" you are up to $567 per person and first class is $469 per person.  The real cost to fly would be ~$700 for my wife and I compared to <$100 in gas to drive.  

I just can't see the advantages to flying anywhere that is less than about a 12 hour drive.  Even then, I'd personally rather drive.  

I just can't see the advantages to flying anywhere that is less than about a 12 hour drive.  Even then, I'd personally rather drive. 

To me it's more about not flying anywhere that's less than 4 hours, if it's in the 6 hour range it'll depend on flight flexibility / cost / our schedule / parking and whether we need a car at the destination. Get up into that 8+ hour range and flights start looking REALLY attractive unless it's a destination that is difficult/expensive to fly to, or if it's something that we're doing as an entire family so I want to avoid buying plane tickets for 5 people, or we want to bring the dog. 

I'll drive from AZ to FL if I'm staying there more than 10 days.  If it's less, then I fly.  I just hate not having my own car to visit everyone I want to see.  Paying for a rental for more than a few days feels like I'm just throwing money into the trash can.

Are you still young and stupid enough to do things like drive it straight through, or single and frugal enough to get a few hours of shuteye at a rest stop in your car overnight rather than stay in a hotel bed? Because that's a long ass drive lol... I just mapped it and it's 25 hours to Pensacola or 35 to Miami, so no matter where you're going that's a haul. 

I realize as a teacher you may have longer blocks of off time in the summer than I do so the extra time might be less of an issue than the extra money, but hell, no matter how much time I've got I'm not sleeping in my car at this point in my life lol.

When I think about that drive all I can say is...

Flying sucks. 

Are you still young and stupid enough to do things like drive it straight through, or single and frugal enough to get a few hours of shuteye at a rest stop in your car overnight rather than stay in a hotel bed? Because that's a long ass drive lol... I just mapped it and it's 25 hours to Pensacola or 35 to Miami, so no matter where you're going that's a haul.

I realize as a teacher you may have longer blocks of off time in the summer than I do so the extra time might be less of an issue than the extra money, but hell, no matter how much time I've got I'm not sleeping in my car at this point in my life lol.

When I think about that drive all I can say is...

From either end, I just get through San Antonio, and stop.  A couple of times (maybe 4-5) years ago, I'd sleep at a rest stop for 4-5 hours, then finish the trip (and sleep once I got there).  Now, I'll get a hotel room, sleep for 6-7 hours, take a much-wanted shower, and finish the drive. 

I just refuse to rent a car for 10+ days and I refuse to be stranded at one loved-one's place, unable to drive 4-5 hours to another loved-one's place.  I REALLY like having my car.

Last time, I had half a day of nowhere to be and nobody to see, and I spent that time driving up A1A along the beach.  It was great.  35 mph, windows down, listening to Jimmy Buffett.  Needed.  Cathartic.  Home.