Tony Little suggested that offering such benefits could help to create a sense of community and involve parents more in school life.
He said independent schools could no longer rely on reputation alone.
But his suggestion was dismissed by one former head as "un-British".
Speaking at a meeting of the Headmasters' and Headmistresses' Conference (HMC), which represents private school leaders, Mr Little said: "What I'm about to say I've seen work extraordinarily well and I would never have believed it.
"In fact, I would have strongly argued against it if I'd been part of it, and it's arriving at a situation where parents as a consequence of having chosen a school, or part of a group of schools, as a consequence of that choice, there are a number of benefits that come their way...
"That is to say, the amount of benefits you can derive, and by benefits I mean reduced flights on a particular airline, or whatever it might be, that the amount of benefit matches or exceeds, the fee that they are paying in the first place."
Speaking to journalists, Mr Little, who is now chief academic officer for the Gems Education group, said he was not aware of any UK schools offering this, but has known of overseas schools in places like the Middle East that are looking at these types of benefits.
While an individual school would find it difficult to do this, it may be possible for a group of schools or an academy trust, he said.
"When you want to create this big sense of community, one way to achieve that is to say thank you," he said.
"Thank you for being part of this particular community of schools. And there is now a move by some schools to find ways, as it were, to give something material back for those who want it.
"In the hope not only that they feel good about that, but they feel more connected to the community, and would be for example, more likely to come to parents' events, more likely to wish to be involved, give their time."
Earlier this year, Gems Education announced it was launching a "privilege and rewards" programme.
The scheme will look for partnerships with "lifestyle brands" in the United Arab Emirates to offer rewards and benefits that help off-set the cost of school fees, the group said.
Mr Little also warned that fee-paying schools needed to work harder to ensure they held their position in a fast-changing world.
"My point simply is that British independent schools, for generations, have been able to live off a set of shared assumptions, which haven't really changed a huge amount.
"And we're entering a world of huge change where, those assumptions, need really clear explanation."
He continued: "In pretty much everything a school does, it has to be much more conscious about how it's transmitting, how it's explaining what it does do."
But the idea of a "reward scheme" for parents was not welcomed by everyone gathered at the HMC conference which was discussing ways to engage better with parents.
Dr Rosemary Taylor, a former independent school head and northern editor of the Good Schools Guide who addressed the conference, said she had not heard of such a scheme and did not think it would catch on here.
"I think it's a very un-British thing to do. When it comes to money and our children I think it leaves us slightly uncomfortable.
"Here it doesn't sit comfortably with us. It feels gimmicky. Is it what parents want? I don't know."
Dr Taylor said what parents really wanted was for schools to get on with the job of educating their children - and doing so well.
Addressing the conference, Michelle Doyle Wildman, policy director of PTA UK, advised schools to consider making a fresh start in how they engaged parents in the school community.
Ms Doyle Wildman quoted a survey of parents by the PTA conducted at the end of last year which found 84% wanted to support their school and 40% wanted to get more involved.
In terms of barriers to involvement, the survey found 40% of parents cited a lack of time and 30% said they had not been asked to get involved.
Ms Doyle Wildman said there were no short-cuts to engaging parents in school life, but that with good leadership, it could become a reality.
"Can you do more to ensure parents and educators are partners in our children's learning and development? Can you play a greater part in supporting and reassuring parents?"
She went on: "What about a consultative body as part of your PTA or a separate parents' forum or council?
"Can you gather insights from the full range of parents in your school community to continuously improve your offering and increase satisfaction?"
She also suggested schools could use the "virtual approach" to engage with parents, using technology to its full potential, for example, by sharing videos of school events.
Fee-paying schools should offer parents "thank-yous", like discounted flights, to encourage them to engage with school life, says the former head of Eton.