Flying with Captain Flanagan this weekend!

Since it’s almost the weekend, I just wanted to provide a quick update on my travel plans. On Saturday I’ll be flying with 30+ FlyerTalkers, routing TPA-IAD-RIC-ORD-SFO-JFK-IAD-TPA. Dulles to Richmond and Richmond to Chicago will be on a regional jet, and there will be 20 of us FlyerTalkers on those flights. Freaky!

As if that’s not cool (crazy?) enough, we’ll get a “behind-the-scenes” tour at O’Hare, including a tour of the ramp tower, flight operations center, etc.

Then the famous Captain Denny Flanagan will be in command of our flight from Chicago to San Francisco, so we’ll get to experience some of his legendary customer service.

After a quick 55 minute connection a few of us will be turning right around to New York on the p.s. redeye. I believe I’m even sitting next to Gray from Wing and a Prayer.

Expect a full trip report. It should be a fun weekend, assuming we don’t misconnect. 🙂

Filed Under: Mileage Runs, United
  1. First off, thanks for the great articles and advice on points! The blog is really well-done.

    Secondly, and yes, I’m new here, is why would you spend a weekend doing that tour? Are you visting each of those places or is the actual flying the point?

  2. True, Gray. All 30 of us misconnecting and ending up in the same hotel wouldn’t be bad either. 😀

    Cube, thanks for checking out my blog and for the kind words. As for why I’d do that, well, I’m what we call a mileage runner. That means I fly for the sole purpose of accumulating airline miles. I earn miles at a cheaper rate than it would cost me to just book the tickets for my travels outright, and it’s usually in first or business class. There are thousands of people that do this, many of which can be found at We even have a dedicated mileage run forum. That means I end up on the road almost every weekend, typically flying for around 36 hours. It’s quite fun, believe it or not.

  3. Thanks for the response. I have tried a couple of times to read the FlyerTalk but it certainly isn’t newbie-friendly.

    It kind of sounds like this particular trip might be a kind of arbitrage – you take these 7 flights to get the miles in order to take more trips. What I have trouble seeing on FlyerTalk is the I part on the ROI. For example your previous post on puchasing a $1 item from a catalog and getting points was great…but that seems to be chump change compared to what you’re doing. How does the ROI work out? How does one get started?

  4. Yes Cube, at times FlyerTalk can be intimidating, both in terms of how advanced the content is and sometimes how rude certain members are. Don’t get discouraged though.

    You raise a good question, and it’s probably the question that I get asked most often — how the hell can I make money from flying when all I’m doing is earning miles for other flights?

    Let me put it in terms of numbers. Last year I spent about $3,000 on “mileage runs,” which earned me over 500,000 miles. Those 500,000 miles could be used for four first class award tickets to either Asia or Europe, or six award tickets in business class to Europe, etc. Simply put, it means I’m paying less than $750 for a first class ticket to Asia which would otherwise cost over ten thousand dollars.

    It’s a bit of a complicated game, but if you enjoy flying it’s totally worth it. I spend almost every weekend away from home traveling, which can either be heaven or hell depending on what type of a person you are.

    Here’s how I construct mileage runs:

  5. Lucky, but you have to also inform Cube that some of us are running for status, not actual redeemable miles.
    With business travel getting slower, I find myself in need of mileage run to retain 1K for next year.

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