The Chicago Seminars: A Review and Awesome Giveaway!

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Update: The autographed t-shirt winner is Elizabeth!  Thanks so much for supporting the Dream Foundation!

I just returned home after a very full weekend at the Chicago Seminars.  It was quite an experience – from hanging out with amazingly knowledgeable Flyertalk/Milepointers, to talking with Tom Stuker (United’s famous 10 million mile flyer), to eating dinner with some of my favorite bloggers/good friends, it was a very worthwhile weekend.  Oh yeah, there were great sessions, too!

Instead of reviewing the information in each session (because I am sure that some other great bloggers have taken way better notes than I did will do that for you), I am going to talk overall about some reasons you should consider going to the Seminars next year, as well as some reasons why the Seminars might not be for you.

Reasons you should go to the Chicago Seminars:

  • You will have face-to-face access to some of the most knowledgeable miles and points experts in the world.  Of course the various speakers are all great sources of information, the attendees almost all have great tips to share as well.  If you want to hear a first-hand account of what it is like to stay at the W Hotel Resort in the Maldives, I can guarantee someone there can tell you.  If you want to hear about what it is like to actually fly First vs Business class in the A380, someone there can tell you.  If you want to know what are the most commonly available international awards, someone there can tell you.  If you want to know how to generate a quarter of a million miles from Skymall with little out of pocket expense, someone there can tell you.  They can tell you the things you can read online, and they can also tell you the things that aren’t printed online that can make some deals even sweeter.

Here Million Mile Secrets is giving some one-on-one instruction regarding booking an international award ticket using Expert Flyer (at least I think that is the site they were using!).  You just can’t get that type of one-on-one help online!

  • The sessions.  The sessions do contain very solid miles and points information.  I saw people frantically taking notes as Gary Leff was discussing the most available international awards from the US!  I saw some people taking a photo of every one of Steve Belkin’s slides so that they can refer to the information later.  Essentially, these guys know their stuff.  It is true that 98% of what is shared is found relatively easily on the popular blogs and/or Milepoint and Flyertalk, but there are some things that just make more sense when you hear them explained in plain English from the experts themselves.  This is especially helpful if you would consider yourself an entry-level or mid-level miles and points collector.  For what it’s worth, I’m not even sure exactly what I mean by entry-level and/or mid-level points collector!
  • It’s just plain fun.  Every meal and break session turns into “social hour” where you get to just chat with old friends and make new friends.  Where else can you have drinks with travel aficionados while wearing costumes??!!  Here is the Mommy Points Pirate and the Frugal Travel Guy “Points Newbie”!

  • Not only is this event fun in a social sort of way, but the connections you make are crucial in the miles and points community.  There are networks of people who share deals only with each other, and the only way in is to get to know them.  Just an example of how these relationships can benefit you, I was guested into the United Club on the way home by a friend I have made through DO’s.  I was given one-on-one tips by new friends I ate lunch and dinner with.  My friend, Million Mile Secrets, is helping mail an important necklace and my bluetooth keyboard home to me as I forgot them in the hotel.  (Side note: I really need to get more sleep!  Can’t believe I forgot those things!)  The point is that human relationships are just as important in the miles community as they are in any other community.  It is a very helpful and giving group and it is worth the time and effort to get to know some people personally.

Reasons you shouldn’t go to the Chicago Seminars:

  • I tried to really talk to people about what they thought of the sessions and the Seminar, and the biggest “negative” I found was when people had a different expectation for the event than what the event truly was about.  By that I mean, if a person only goes to the event because they expect to leave knowing the top-secret handshake and password that will open up all award seats at the “saver level” and/or score you nights at the Park Hyatt Tokyo at $49 a night, then those expectations may not be met.  There are some codes and deals shared at the conference that aren’t overtly discussed on most of the major blogs, but if you already spend hours a day on Flyertalk and/or Milepoint and go expecting to hear the Holy Grail of point earnings that is not buried anywhere in the million threads online, then you may not feel you got your money’s worth.

I think that is an issue that is really just reserved for those who would probably consider themselves “expert” in the miles community.  In truth, I think most of those “experts” did still learn some things at the Seminars, but it is important to manage expectations appropriately.  You will hear and learn from the best at this Seminar, but that doesn’t mean there will always be some top-secret-decoder-ring-never-before-discussed-anywhere-game-changing information shared in the sessions you attend.

I personally think that The Frugal Travel Guy and toomanybooks did an amazing job with putting on this Seminar.  As an attendee, there were no issues at all that I encountered.  I thoroughly enjoyed the sessions, and had a great time connecting with new friends and re-connecting with “old” friends.  I think one of my favorite sessions was with Captain Denny, and he didn’t share any miles and points tips!  Don’t get me wrong, there are many miles and points tip shared at this Seminar, but there are other great takeaways for me as well.

I gave away a few shirts yesterday, partly to help bring a piece of the Seminar to those of you who couldn’t make it, and partly to help with some slow-ish t-shirt sales.  When Tom Stuker, United’s famous 10 million mile flyer, came to the Seminars today I had an idea right as he was leaving to buy one more shirt and have him sign it for one!

To catch him before he left, I literally ran after him like a groupie chasing a rock band.  I would never in a million years do that for myself, but I will make a ridiculous fool of myself for you all!

Not only he is famous in his own right for having that many “butt in seat” miles with United, but he also has a reality television series coming out early next year on Spike TV called “Car Lot Cowboy“.  So, not only do you get an official Chicago Seminars t-shirt (size XL), but you get it autographed from the next reality TV star.  🙂  Here’s the catch…. in the spirit of the Seminar, I really want this shirt to also help raise awareness for one of The Frugal Travel Guy’s favorite charities, The Dream Foundation.  Essentially, you can donate airline miles to this organization and they will use them to help grant “final dreams” for adults with a life-limiting illness.  At the Seminar this morning The Frugal Travel guy got everyone choked up (himself included) when he spoke from the heart about both this organization and his other favorite charity, Wounded Warriors.  Most of us of us in the miles and points community are so fortunate in many ways, so it is always important to pay that forward to others in need.  Donating a few miles is a simple way to do that.  Even 100 miles can be a great help to this organization.

So, the way you enter to win this super awesome autographed shirt (that I made a fool of myself to get!) is to post a comment between now and 11:59PM CST on 10/31/11 saying that you want the shirt, and telling me one thing about the Dream Foundation.  I do not want you to just copy and paste something someone else said (I reserve the right to disqualify!) – I want you to at least go to the Dream Foundation website and check out that organization.  If you feel you can spare a few miles, then please also take this chance to share some miles with someone who really needs them.  The wining entry will be selected at random.

Please feel free to ask any questions about the Seminar, and I will be happy to give an honest answer!  This year I wasn’t a speaker or a sponsor, just an attendee like everyone else, so I had a chance to have a good experience from a participant point of view.  I really hope that many of you will decide to join me at the Seminars next year!  Good luck on the shirt and Happy Halloween!

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. […] Mommy Points has another great post on the weekend.  She  explains that you may be disappointed with the conference if you expected to find methods to book the Park Hyatt in Tokyo for $49 or the secret way to open up award availability at the low level. Mileage Runs Workshop […]


  1. Thanks. Would be great to get the shirt. Your link doesnt work. But the first thing I would do after getting a job is to adopt a dream. The dream foundation is a great idea.

  2. Trader Joe’s is such an amazing organization, and it doesn’t surprise me to see them listed on the Dream Foundation. I’m amazed how often I see them listed as a donating company. They are a HUGE provider to the local food pantry in my area that is now feeding over 700+ families a month.

  3. Already have a shirt since I was at the seminar this weekend, but wanted to give you kudos for such an amazing, entertaining and thoughtful blog. You had a few shout outs from the presenters which was rightfully deserved!
    Didn’t formally meet you at the seminar, but I believe I helped you do a bit of cleaning duty with cup clean ups!

  4. MP, great to meet you at the DO and had breakfast together with other fellow FTs Saturday morning! Your review is great too. I had a great time. What I gained most was the DO really opened my mind. The unique thinkings behind all those activities were amazing. I bought my shirt at the DO, so good luck on whoever win this great prize. See you @ the next DO or earlier. -:)

    • @Allen, great meeting you as well! There is some unique ways of thinking that happen in this community – very helpful to hear how others approach things for sure!

  5. It was nice meeting you at the seminar and am glad you had a good time. You are absolutely correct: the seminar is not for getting the secret handshake deals, but rather an opportunity to learn some incremental information and network with some great people. I learned a lot of new things, not secrets by any means, but things i was just not aware of.

    • @MMS, ha ha. Yes, this is what the pirate who disappeared to sleep (much too early!) looked like. So great to see you and Emily this weekend. 🙂

  6. Great write-up about this weekend. It was my first time attending and I had a great time! It was so nice to finally meet you! Frugal Travel Guy and toomanybooks did an excellent job and I will definitely be back next year. 🙂

  7. Great summary of the seminars for folks like myself who couldn’t go. You look great as a pirate.

    I’d love to get the t-shirt and I love that you pick the Dream Foundation to support. I hadn’t heard of it before you mentioned it, but looking at the site it appears to be an organization similar to the Children’s Miracle Network except it’s for adults. Folks can support the organization by adopting a dream or joining the Dream Team with a $25 donation.

  8. What a great thing for you to do. I hope people will actually take the time to donate a few miles to this cause. About 8 years ago, the Dream Foundation sent my sister to Hawaii about 6 weeks before she passed. I have been encouraging folks to donate miles to this cause ever since. It is such an easy way for this community to give back.

    • @Shane, wow. What an amazing story about your sister. I am so sorry to hear of her passing, but glad that the Dream Foundation was able to help her get to Hawaii. Thanks for sharing!

  9. Hey! enjoyed meeting you and loved the Chicago DO! Wouldn’t mind having a shirt that the 10 million mile man signed!

  10. Interesting organization.. Since I already won a t-shirt I will be sitting out on this win 🙂 Have some Delta miles that I won’t be needing so I might be giving them away this weekend! 🙂

  11. Mommy Points: Thanks to meet you again and I am surprised to my photo in today’s blog. I told my friends today to check your blog to see my photo.

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