Even though his 2-year-old is young enough for free admission, Day said, the cost of tickets for three days would amount to $1,455 if his family wanted to visit multiple parks in one day. A hotel on the sprawling Walt Disney World Resort around Orlando would set them back at least $500 a night. In all, his estimates placed the trip between $4,000 and $5,000, with the family driving from Bowling Green, Ky. — an “incredible investment,” he said in an email.