Chicago Seminars… aka Crazy Frequent Flyer People like Stephanie

Since we’ve started traveling, we’ve been asked more than once if we are independently wealthy.  Although I wish we were, the truth is, traveling the way we do it is not as expensive as it may seem at first glance.  Many people we know can do what we are doing if they are serious about it and are willing to make some daily sacrifices and lifestyle changes, take some risk, and put in some hard work.  For Elliott and me, there are a few key components that enable us to do this:

  1. Giving up lots of little things we’d like to have over the years, saving the money instead
  2. Couch surfing
  3. Using frequent flyer miles and hotel points

We will eventually post about all three components, but today’s post is focused on #3.  For those of you who don’t already know, I have a bit of an obsessive hobby.  Over the past two years, I’ve collected over two million frequent flyer miles, and most of them are not from flying.  Elliott is not super involved but he does agree to do small tasks once in a while since two people equals 2x the miles for every promotion I find.  In April, he let me drag him along to my first ever frequent flyer mile conference, and I was thrilled when he thoroughly enjoyed himself.  At that time we found out the dates for the Chicago Seminars coincided perfectly with our driving trip across the country – the seminar was planned for the exact weekend we would be passing through Chicago!  So we put the brakes on for a few days and decided we absolutely had to attend.

If you’re still stuck on “two million frequent flyer miles”, you’re probably curious how we’ve gone about this feat.  Let me first state that it truly is an obsession, and a super time-intensive one when done at this level.  Secondly, let me say that you can still do a lot of free travel if you get involved at the rate of a mere mortal, so do not be afraid.  The basics involve 1) living in the US, or at least having a US address, 2) watching out for credit card offers that come along with huge sign-up bonuses, and 3) opening said credit cards and fulfilling the criteria to earn your bonus miles.  There can be a LOT more to it, and the way I do things, there IS a lot more to it – probably a university degree’s worth of learning!  But I’d venture to say you could very easily get 100k free miles per year, per person in your household doing minimal work.

The seminars we attended were mostly made up of people who are in the game at a pretty intense level, but there are also newbies at these conferences, and every experience level in between.  The nice thing is that everyone there loves to travel, loves to save money, and loves to share what they know and learn what they can from you.  At this particular conference there was a beginner and advanced track so Elliott and I split up often and then shared notes.  For beginners (which I’d assume y’all are,) there was the following:

  •  Rookie Bootcamp
  • Frequent Flyer 101: Pudding Guy and Credit Cards for Newbies
  • Elite Status – Challenges and Fast tracks
  • Mileage Runs
  • Award Booking
  • Gift Card Churning and Shopping Mall Bonanzas

There were actually several other classes in addition to these, but this list should whet your appetite.  Many of you are probably confused by some of the terminology used in the class titles, but that’s okay.  While some of you are asking who the heck is Pudding Guy and what is a mileage run, others are wondering if the Shopping Mall Bonanza involves being at the local mall all day.  No worries.  If you’re interested in learning more, just let me know!  And here are a few links to get you started:

Even if you’re not interested in learning more, the Pudding Guy is a REALLY engaging, if not insane, story.  Check it out!


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