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My rule for work, is about 5.5 to 6-hours to drive will likely take longer to fly if it's a connecting flight (and if it doesn't get grounded or delayed).
For family trips don't forget to include food and lodging into the price (plus pain and suffering).
Our family rule is 8-10 hours in the car or bite the bullet on flying (you have to figure time as money if you have limited vacation time or time at your destination).
There's generally 4 of us, so we just rent a car to cut the wear and tear on the newer sedan (or if you need something bigger for hauling everyone and cargo).
I can't put a dollar figure on it since every family's budget is different.
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“If we knew what we were doing, it wouldn't be called research” ― Albert Einstein
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