View from the Wing on Video: Award Booking and Elite Status Advice

Conde’ Nast Traveler has just posted three videos featuring my advice on a variety of subjects.

In this week’s edition of tips from our Top Travel Specialists Collection, we hear from Gary Leff, our specialist when it comes to award tickets and cashing in all manner of frequent flier (and frequent guest) points.

In these clips, Leff talks about the very best time to cash in your frequent flier miles for free seats—and it’s not necessarily on the 331-day timeline that’s so commonly thought of as the gold standard for award bookings. Leff also shares good tips about getting into business- and first-class cabins, where service is naturally that much better. As aircraft shift and global airline alliances change, Leff shares his tricks for making sure you’re in the best seat available.

In another clip, Leff has tips on hotel award programs, which offer freebies far beyond just free room nights, including free upgrades, free internet access, and oftentimes free late check outs.

The subjects of the videos are:

  • When is the best time to book award travel?
  • What are the best hotel perks for business travelers?
  • What are the best first class rewards?

Each one is 3-5 minutes. So it won’t take long for you to watch them all.

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 »

More articles by Gary Leff »



  1. Cools video and tips. It was finally nice to meet you (even if it was not in person lol)

  2. Is there a good reference to look up how many days in advance a given arline loads its schedules? You mentioned that the timelines can vary.

  3. As always, great and concise info that make all our lives better!

    Gary you mentioned in Video #1 changing your flight from Paris back to the states the day before you departed. Can you please walk us through the process of doing that from a non US location? I can picture seeing the availability online, but shutter to think trying to call an airline and coordinating from overseas.

    Also, is this a service that Book Your Award would consider offering? Ie watching for premium inventory to open up while someone is travelling?

  4. @Howard – I cancelled one award and booked a new one online. But I usually use Skype on my cell phone to call English speaking agents in any case. 🙂

  5. Great call on Skype! Just curious, I saw that Milage Plus has a whole list of contact numbers in Europe. Do you use EU milage/airline award offices in the specific country you are in (for instance Brussels) or call do you always call the US contact number?

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