Chicago Seminars – the 5x tribe descends on ORD

Book Delta to these events.

The rains and tornadoes disrupted O’Hare as the event concluded. A mad scramble of super-duper-lifetime American and United elites ensued for quickly disappearing seats on remaining flights. Over in Delta land the few of us were chill with confirmed seats.

Last year I wrote a comprehensive recap. This year I am a day behind and already there are dozens of excellent reports. So, instead here are a few moments that stuck with me:

  • The Office Depot across from the hotel was staked out the day before the event even started.
  • When staying at hotels on awards/prepaid bookings/airline accommodations consider putting a small charge on the room and you may get lucky with points credit.
  • Amtrak has tremendous value award redemptions via Chase Ultimate Rewards points, bikeguy opened my eyes, a great way to get family out of the house for a long. slow trip. The jewel is the Coast Starlight between Los Angeles and Seattle.
  • Chase Inside Access and SPG Moments can be a good deal for events otherwise inaccessible. I forget whose lecture covered that.
  • The Chase Ultimate Rewards mall has different bonuses by credit card, if you have several, check them all (I have none!). A great point from an attendee in a Q&A.
  • Calling Delta for complex international awards, ask for Round the World Agents, the front-line agent will be happy to be rid of you and you will get an agent more familiar with partners and complex itineraries, thanks Delta Points!
  • And also for Delta, and probably others, when agents don’t believe, say “Price it as booked.”
  • Marshall Jackson explored cruising, a corner of the travel world totally new to me. There are so many ways to book cruises, but a number of people have fund the Travelocity Price Guarantee to be particularly useful with volatile cruise prices.
  • Starwood has a site for last-minute Europe deals, Beat the Timer for stays within 72 hours.
  • Programs like American Express Membership Rewards, Chase Ultimate Rewards and Starwood Preferred Guest have partners. And partners have partners. Lots of them. Don’t forget to think through the entire web. The Points Guy lays out his talk in this post.
  • Status matches/challenges for hotels can be quite generous, but some airlines are pay to play, and then you can easily end up spending a hefty chunk of change to meet challenges, so research very carefully prior to take off. Mommy Points had a great, systematic presentation for the major programs, and a fun ‘Top 10‘ from the event.

Some mileage earning legends were in attendance and held excellent sessions. beaubo, in addition the brilliant award bookings, has sage advice to be loyal to none but yourself and take advantage of what you want because things always change. pudding guy, just back from Easter Island has such a positive approach to keep the focus on having fun, though unfortunately I missed his session. And mrpickles had me furiously scribbling down SPG tips. Best was seeing mrpickles at lunch, sphinx-like, dispensing occasional oracular pronouncements in a low voice, all the while me knowing he was silently earning more miles during that meal than I probably earn in a month.

Plus so many tips learned from fellow attendees. Networking is the biggest value of the event.

Rick, Frugal Travel Guy, ran a tight ship as always and we all owe him thanks for a superb event. Not exactly a crowd of un-opinionated sheep, so a tough group to corral!

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13 Comments on "Chicago Seminars – the 5x tribe descends on ORD"

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Juicy. Any SPG tips (from Pickles) that you could share?

Rapid Travel Chai

@JettyBoy – sorry, I am not going to try to slice any pickles, actually with SPG was more a general session for non-experts like me to get up to speed on SPG, and if you check his twitter feed he is letting out some tips. SPG points are hard to find shortcuts to earn. I hope you can attend next year!

Marshall Jackson

Very nice seeing you again. Great summary.

Joshua Pickles


Thank you for your kind words. You guys at lunch got me thinking more about “passive” mileage earning and just running some quick numbers I have figured out that I am earning about 1.28 miles per minute 7/24/365. This is in addition to earnings from flying, credit card spend, and credit card sign up bonuses. This may be a potential mileage earning that people are missing out on.

I will have to think more about this and on how to increase my (MPM) mileage per minute.

Rapid Travel Chai

@Joshua Pickles – we will all be waiting on twitter for clues!


Good Recap!

Rapid Travel Chai

@ORD-TGU – great to meet you in person and thanks again for your Amex Hilton tips.

Jimmy @TravelByPoints

Probably the best and most valuable/informative recap of the #Chicagoseminars! Thanks, RTC. I was contemplating a trip on Amtrak from SEA to YVR with Chase UR points until we decided not to do YVR.

Rick Ingersoll

MrP, you got me beat. I’m at .925 MPM. I think you have discovered a great new Measurement. What all are you including besides deposits and automatic payments to mileage earning credit cards?

Miles per Minute

I hope you blog about it as it is your measurement. If not, I’ll gladly bring up the concept


@Stefan — you are earning 675,000 miles per year “passively”? What exactly are you counting in this number?

Rapid Travel Chai

@Gene – that is mrpickles, not me, and I am eager to hear more from him!


@Stefan — Oh, that explains — must include diamonds from Costco or something. 🙂


@mrpickles- I also enjoyed meeting you and your SPG breakout at #chicagoseminar.
Maxing out BankDirect is 240k/yr or 0.46 MPM. Wondering what other miles deals one could say were in this passive definition. As Rick asked, do we count automatic payments on CC? 5x on IB telecomm-related autopays is a nice number.