How to Make Money Booking Award Tickets for People

Reader J. Clifton asked,

What is a good way for someone to get into award booking? After getting involved in this hobby, I’ve thought it might be a fun way to earn some extra money.

I’m a big fan of developing multiple income streams, don’t quit your day job but trading idle time for a side business can really make a difference at the margin.

And one way to know what skills you have that could be marketable is to ask what questions are people always asking you, or things they’re asking you for help with?

If one of those things is how to use their miles and points, you may have a market.

Do go in knowing though that:

  • It’s actually harder than you’d think with all the possible problems you can encounter
  • There’s a lot of competition in the space
  • It’s hard work and difficult to scale

And have a point of view on what you will do if:

  • You have someone transfer points, and the seats they wanted become unavailable? Or if the website you searched space on was showing phantom availability?
  • You aren’t careful and suggest a routing that actually violate’s a carrier’s routing rules?
  • A ticketed award gets screwed up — maybe a flight cancellation happens, and the issuing carrier doesn’t notify the traveler or you? or a flight number changes, the ticket doesn’t get auto-reissued, and the space gets cancelled?
  • You present an itinerary to a client that you get approved, but it was connecting — and they also specified non-stop only — and now they’re unhappy?
  • You’re dealing with miles in a program that won’t speak to you — and will only talk to the client?

There can be innumerable frustrations along the way, clients who don’t like what seem like perfect itineraries or people searching for awards but not ready to actually pull the trigger when you find exactly what you’ve asked for. And you may present an itinerary only for them to go off and book things on their own.

All of these scenarios are things you need to think through because they can happen. I’ve always taken the view that I only want happy clients, and don’t take money until we’ve been able to come up with an award itinerary that meets agreed-upon parameters. And I don’t sweat the small stuff, if overall you come out ahead then if a given itinerary doesn’t make someone happy when it should so be it.

I’ve also on more than one occasion ‘made itineraries right’ when I probably didn’t have to, and spent many hours escalating things with airlines on behalf of clients.

People often come to me as well wanting me to push the envelope on what programs allow, or to buy or sell miles. And while there are itinerary tricks I might pursue for friends, I will not break airline rules for compensation, period. That’s a line I draw and I think everyone needs to think through their own lines as well.

There are also clients I don’t really want to work for. I declined to book an award for a woman to take her 8 year old daughter to Iran and leave her there. I don’t especially want to book for folks that already have awards and want to get rebooked to save on taxes and fees — a legitimate pursuit, but I prefer my time to focus on making travel possible not merely helping people improve at the margin. I like it when people feel the service fee is the best money they’ve ever spent, something I hear often.

Point is: it’s hard to get into this space and do it well, precisely because award booking can be hard (hence the existence of these services in the first place) and because you’re depending on airlines whose agents and systems are of variable quality but the whole point of the service is for you to take these vagaries out of the equation on behalf of the client.

If you’re prepared to do this, and you’re experienced in booking awards enough to do this, then you face myriad competition from established players in the space — folks like Lucky from One Mile at a Time and Matthew from Live and Let’s Fly (not to mention me and my award booking partner Steve).

Nonetheless, it’s incredibly enriching to help people make their dream trips come true — to give them something that they would never have been able to experience on their own. The honeymoons, the 25th anniversaries, the dream trips and family vacations and the trips abroad to adopt a child. Award booking can be incredibly enriching.

The way I got started was that I frequently get requests for help because of the blog, and I would pull up awards for folks regularly, I was asked for a bit more hands on help one day and nearly six years ago I decided to charge. Then I spun up a website. And it was early on and I managed to catch the attention of some media and got exposure.

I can’t tell you how to get started other than to spin up a simple website yourself, and to start charging the people that already ask you for help. And to ask them to spread the word.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. I see this as normal career progression – one works for someone else for a time, and then hangs one’s own “shingle”.

    At the rates charged by Gary or Lucky (or similar) you’re not going to compete on price. The risk is too great for saving $25-$50 per ticket. Given the complexities, these are big tickets. And there’s no way to verify product differentiation – how are you any better?

    Warren Buffett speaks about the importance of “moats” around a business. I don’t see any chance for “moats” for a new entrant to this business, without prior experience in one of the “moated” entities.

  2. One would be better to become an outside agent for a travel agency. Benefits are better and the agency covers you for errors and omissions. Although one would need experience in selling travel, which most people do not have.

  3. @J Clifton… The real revenue opportunity is credit card links, my friend. ABS is merely a loss leader to get the customers in….the dough is made with the links.

  4. Gary, great write-up! I’ve booked more then my fair share of awards for family and friends (of course gratis), and I can’t tell you how many times “no good deed goes unpunished”. Usually it’s IROPS and somehow that becomes my fault when flights don’t go as scheduled! For friends that I think will be too big a headache or not my responsibility, I just send them to you/ben/or matthew.

  5. In the current issue of Entrepreneur magazine I noticed a list of 100 home base franchises. Surprisingly, one that involved selling cruises, aka travel agency, was in the #2 spot. I’m guessing the upfront costs, $2K-$22K, entice people to invest in these franchises, except now airlines and credit card providers now offer cruises.

    While I have little knowledge on helping others to travel and get paid for it, I do know a few people who tried to be a successful licensed real estate agent. Beside the necessary prep, too often you become a long term unpaid ‘gopher’ at a real estate office.

  6. @JClifton, one advice I have is to at least become an expert in one of the alliances: skyteam, star alliance, or oneworld; and then apply to work for one of the established award booking services out there (Gary listed a few above and so did other commenters.) I’d work for them for several months to learn the ropes before doing something on my own.
    What I’ve seen other people in boardingarea do as well is to offer doing award booking for free for a few months. I recall Canadien km doing this a few years ago. I’m not sure if that was successful or not but I bet he learned a lot in the process.
    Good luck!

  7. I do not see how you can deliver for the prices you charge (not that I doubt that you actually do).

    I’ve been helping a colleague with her Thailand honeymoon plans. She’s made quiant comments like: you mean the DCA-LGA leg is included in the cost of the transpacific? and you mean that if I schedule in a 17 hour layover at HKG I can clean up at the CX arrivals lounge and go into Hong Kong for the day?

    The process of sitting someone down and asking enough questions and then seeing how those answers match award availability is terribly time consuming. I’m trying to do right by my colleague, who has made her honeymoon planning an 18 month endeavor, starting with CC sign up points, and now bookings.

    But, seriously, doing right by a client requires being smart and creative – fairly high dollar skills. Someone with that skill set can easily make good coin in another business (and I do all right). Under the circumstances, I’d go into the business only if I could charge at least $300 per reservation.

  8. Flight Fox is an easy way for anyone to make money doing this without the overhead and hassle.

    Just pick the requests you want to help with – and their platform handles the communication, matching, and payment.

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