Chicago Frequent Flyer Seminars: Day three summary – Sunday 10/30/11

The 2011 Chicago Frequent Flyer Seminars concluded yesterday and it was an incredible weekend filled with an amazing amount of mileage and point tips that one could never process on their own. Airline miles I have pretty down pat, but I did learn a few great hotel point and credit card maximization techniques.

Yesterday started with the “Sponsors Workshop†where all the event hosts had their opportunity to present their featured products and/or websites. Here’s the great thing… unlike many sponsored events, the Chicago Seminar sponsors were people who we uber frequent travelers actually care about and therefore, none were a boring sales pitch as would be found elsewhere. First up was Chris of ExpertFlyer.

a group of people sitting in chairs in a room


I’m already a subscriber, but his presentation went into detail about specific functionality the site provides and I picked up a couple of tips. He also provided a 15% discount code for new memberships. Next up was Daraius of Million Mile Secrets. If you don’t already know about his website, he shows you how to get “Big travel with small money.†Fairly new to blogging, he has become my go-to source for current airline & hotel bonus opportunities, particularly with credit cards.

a group of people in a room

Million Mile Secrets

Next up was Cara with ITA Software and their incredibly helpful tool, Matrix Airfare Search. Once I find a great fare on FareCompare, the ‘Matrix’ is my next stop and is by far the most dependable and accurate search engine of its kind.

a group of people sitting in chairs in front of a projector screen

ITA Software

After Cara, Brian from The Points Guy provided an overview of his two websites, which are a must read if you’re wanting to rack up some serious miles and points. He then proceeded to give out some amazing prizes to raffle winners.

a man giving a presentation to a group of people

The Points Guy

Then it was time for the BIG raffle drawings. All proceeds went to charities and I was surprised to win four 50% off rack-rate Starwood Preferred Guest certificates, each offering the discount for up to five consecutive nights at any participating hotel. I donated all of my United and Continental drink certificates earlier in the day and was hoping they’d just pass them out to people who wanted them (as they did the previous day) and didn’t expect it to be a part of the raffle, but… one guy won my whole lot!

a group of people in a room

Raffle 1

a paper with a blue ribbon around it

Raffle 2

Then it was time for either a discussion with ‘The Pudding Guy’ and ‘Mr. Pickles’ (two legends in our mileage & point field) or moderated breakout sessions on specific airline and hotel programs. I went with the latter as the 10-million mile man of United Airlines, Tom Stuker, moderated the United session. I went to his milestone event in Chicago earlier this year, so was eager to hear what he had to say. No worries, Tom, I haven’t posted anything you said on this blog. 😉 And yes, United, he loves you and said nothing to disparage you.

a man in a cowboy hat

UA Tom Stuker 1

a group of people sitting around tables

UA Tom Stuker 2

Lunchtime hit and I went for a drive. I grew up in Chicagoland and drove past the old United headquarters on Algonquin Road in Elk Grove Village. I interned there in 1993 in Flight Dispatch (EXODD) and also worked there full-time in 1998 in Inventory Management (WHQIM). HQ has moved downtown since my days there, but the lot remains and is up for sale. Not pictured are two more buildings on the expansive land that housed Flight Dispatch (a four-story building) and the Flight Attendant training center and “hotel†(which I believe is still owned by United and active today).

a sign in front of a building

United old HQ2

a tree in front of a building

United old HQ1

Then it was back to listen into the one and only Randy Petersen, who founded Flyertalk, MilePoint, InsideFlyer and is basically the “god†of all things miles and points. Randy went into how he got started, the evolution of Flyertalk and provided his thoughts on how airline frequent flyer programs might change in the future.

a man standing in front of a group of people

Randy Petersen

The final presentation of the weekend was by Steve, aka ‘beaubo’ on Flyertalk and elsewhere, and he presented a uniquely different approach to why mileage running and gaining elite status might not be the best way to go. It was incredibly thought provoking and might become our future. Airlines are currently more heavily driven to incentivize higher-fare paying customers and the way we currently achieve both elite status and redeemable mileage will definitely change in the near future.

a man giving a presentation to a group of people

Steve aka 'beaubo'

I consider myself an “expert†at what I do. Yes, I have the mileage running game down and I qualify for elite levels in hotel loyalty programs, but I was blown away with the knowledge imparted this weekend. I said it in yesterday’s post and I’ll say it again… if you’re on the fence about coming to an event like this: Do it! You won’t regret it and the information you receive, as well as the all-important human connections you’ll make, far exceeds the cost of travel and admittance fee.

[Be sure to check out the preceding day here!]



  1. Hello – I paid to be at the event but had a conflict and could not attend. As I paid well in advance is there any way I can receive the materials that we provided?

    • Well, no materials were handed out. Each speaker either talked from the hip or used a powerpoint-style presentation. You might consider contacting them individually.

  2. Darren, thanks for posting this series — it will be a great reference for the future. It was great meeting you!

    • It was great meeting you, too and thanks for the kind words. I’ll be there next year! (and will definitely hit the credit card side… I need to churn more often than I do!)

  3. I see myself in one of those pictures! 😛 Great summary of everything. I had to leave early Sunday to meet up with a friend so I missed Randy/Beaubo’s talk. Sounds like that would have been an interesting talk to sit in on.

  4. Thanks for the great review of the Chicago DO. It looks jammed packed with great information and strategies for maximizing miles and points!

    I will have to join you guys next time! =)

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