Chicago Frequent Flyer Seminars: Day two summary – Saturday 10/29/2011

If there’s only one day you can attend a future Frequent Flyer Seminar series, it’s definitely the Saturday session. Yesterday was packed at the 2011 Chicago Seminars and featured an incredible amount of concurrent discussions on all things airlines, credit cards, hotels, miles and points. When booking your ticket for the event you select your choice of same-timed discussions most appealing to you, but as today revealed, it can be a tough choice and people often overflowed into another room. This, then, becomes reason #1 why going one year isn’t enough.

First up yesterday was the introduction by Rick, the Frugal Travel Guy and Rookie Bootcamp with Dave, aka “bikeguy†on Flyertalk. Rick went over some housekeeping items and acknowledged the sponsors, host hotel and everyone who volunteered to help out at the event. Dave’s talk definitely went beyond just the “rookie†level and included the topics of:

  • Blog resources
  • Mileage running
  • How to get airline, hotel & car rental status (and their importance)
  • Airline alliances
  • Mistake fares
  • The value of a mile or point
  • Delta’s new 72-hour award booking rule
  • Website resources for frequent flyers
a group of people sitting in a room

Rookie Bootcamp w/Dave

Want details? You’ll have to book a ticket for next year, as the items discussed are often proprietary to we frequent flyers and are meant to only be shared at these types of events – Reason #2 why coming to this event is so important. Next up was Award Bookings with Gary Leff, author of View From The Wing on He has a “PhD†in award travel and imparted an incredible array of helpful information including:

  • What’s possible with points and miles
  • Easy premium cabin award availability markets
  • Best value awards
  • How to make the best use of Delta’s “SkyPesosâ€
  • How to prepare for calling an airline reservations agent
  • How to find award seats that CSRs say don’t exist
  • Helpful websites for searching & planning award travel
  • Talking yourself out of change fees
a group of people in a room

Award Bookings w/Gary

All throughout the event yesterday, you had the opportunity to mingle with fellow enthusiasts to gain even more insight and experience from pros who know how to maximize their mile & point accounts. Lunch was another one of those opportunities, whether standing in line or sitting at one of the many tables talking to each other. Hence, Reason #3 why you should attend this event!

a group of people in a hallway

Lunch line

Be sure to watch ABC Nightline mid-November as a camera crew was on-hand interviewing people, filming some of the seminars and following us around taping some casual conversations. The air date is unclear at this point, but likely before Thanksgiving.

a group of people in a room

ABC Nightline

After lunch, Ben/Lucky who authors One Mile at a Time on BoardingArea gave several consecutive lectures imparting a dizzying array of knowledge. Second up (as I missed his Hyatt & Priority Club talk) was his discussion about the Starwood Preferred Guest loyalty program. He went over:

  • Elite tiers
  • How to get upgrades
  • What’s a Starwood point worth?
  • The power of Twitter during service failures
  • Ways to get unpublished discounts
a group of people in a room

Starwood Preferred Guest w/Ben

After Ben, United Airlines Captain Denny Flannigan took the floor and revealed his unique, heartfelt and sincere approach to how he manages both his job as a Boeing 757/767 pilot, and his approach to customer service. Honestly, his talk was the highlight of my day. I could (and will) write a unique post about him as what he does for both United employees and customers is so above & beyond what you would expect, it literally choked me up and gave me goose bumps – Reason #4 why you should come next year.

a man giving a presentation to a group of people

United Captain Denny

Ben ended up moderating at least four of the sessions yesterday and he is by far the most astute, contentious and indefatigable 21-year old expert public speaker that I’ve ever met – Reason #5 why this event is not to miss. His passion for our “hobby†has allowed him to do what he does full-time and it shows during his presentations. He hosted the next two seminars covering Mileage Runs and fielded a dizzying array of questions from the audience, all of which were answered not only correctly, but with personal insight from his travel experiences. He went into:

  • Which airlines to select
  • How the game has changed
  • Tools for constructing mileage runs
  • Detailed step-by-step instructions on how to book one
  • Fare basis codes
  • Website tools that aid in finding mileage runs
  • How to maximize your opportunities for a bump (volunteering your seat)
  • Routing rules
  • Fare rules
  • Domestic vs. international mileage runs
  • A Q&A session that could have gone on for days
a group of people in a room

Mileage Runs w/Ben

At the same time as Ben’s Mileage Run discussion, Brian, The Points Guy, was giving an equally informative talk on airline & hotel Credit Cards, bonuses, and churning:

a man standing in front of a group of people in a room

Credit Cards w/Brian

After the last seminar, there were social gatherings to attend and a Halloween party from 8:30pm to 10:30pm, but I unfortunately had other commitments and instead met up with old friends having grown up in Chicagoland. I’m sure it was an incredible time at the host hotel.

Today brings another round of seminars including a Sponsors Workshop, moderated breakout sessions on the various airline and hotel programs, discussions with “Pudding Guy†and “Mr. Pickles,†two legends in the mileage earning game, and Cherry Picking with “Beaubo†and BoardingArea’s founder Randy Petersen. I hope to post today’s summary tomorrow and I’m certain this will bring reason #6.

In the meantime… if you’ve been on the fence about whether or not to attend this event: Do It! If you’re not local, no worries. The sheer knowledge you gain from attending will more than pay for any expenses required to get here. I’m not certain if it will be in Chicago again next year, but I’d suggest monitoring the threads on Flyertalk and MilePoint for details on next year’s event (but look for the 2012 listings, not those links I provided). You won’t be disappointed.

[Be sure to check out the next day here]



  1. The event sounds great, thanks for the write up. Is the next seminar a year from now, and are there other similar seminars coming up soon?

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