5 Takeaways from 2017 Chicago Seminars

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I had the pleasure of speaking at the 2017 Chicago Seminars this weekend.  My speaking topic was Kimpton and how awesome their award program is (was?).  Several other bloggers spoke at the 2017 Chicago Seminars as well and shared some really amazing tips and tricks.  Unfortunately, we’re all sworn to secrecy (so register to attend in 2018!), but there are still some great takeaways from that I can share with our readers.

Related posts:

The 2017 Chicago Seminars

For those of you who don’t know what the Chicago Seminars are, it is an annual travel conference where some of the most well-known bloggers from around the country come to share some of their best tips, tricks, and strategies to maximize your travel dollars and rewards.

The 8th annual 2017 Chicago Seminars were held during the weekend of October 20-22 at the Holiday Inn Elk Grove near Chicago’s O’Hare airport.  The entire hotel is reserved for guests of the conference.  And I highly recommend staying on site so that you don’t miss any of the late night conversations where some of the best tips and tricks are shared among friends.  There is a hotel shuttle that runs to O’Hare – they charge $5 each way, which is way better than an Uber or Lyft.

Registration generally opens about 6 months in advance of the conference.  You can find plenty of details in the FlyerTalk forums related to the Chicago Seminars.

Some of the speakers this year included:

Many bloggers share slimmed down versions of their presentations, so follow their blogs to keep an eye out.

And the 2017 Chicago Seminars had some great sponsors.  I use many of their products, including The Plastic Merchant, Expert Flyer (use our referral link for the best price!), and Reward Stock.

5 Takeaways from 2017 Chicago Seminars

Here are my 5 most important takeaways from the 2017 Chicago Seminars:

1. Direct is not always best

Time and time again throughout the presentations, we were shown examples where it made more sense to use miles and points with partners than directly with the airline you’ve earned the miles.

To put it another way, you may be able to use fewer miles to book on the airline you want when redeeming miles from a partner airline.

2. No doesn’t always mean “no”

Ok, in some situations, no ALWAYS means no.  I’m talking to you Harvey (and everyone else like him)!

But when you’re looking to redeem miles and points, being told “no” doesn’t mean the end.  Often you can hang up and call again (aka “HUCA”) to find a phone agent more willing to help you out.  And, worst case, don’t be afraid to escalate to a supervisor if the phone agent isn’t following the rules.  Sometimes, we know the rules (and the loopholes within those rules) better than they do.

3. Take Advantage of Sweet Spots

When looking to use your miles and points, picking a flight from Point A to Point B is good.  However, every loyalty program has certain sweet spots where you can redeem for insane value well basic a basic redemption.

For example, Alaska Airlines allows free stopovers on one-way tickets.  If you book two one-way tickets, you can visit 2 extra cities on the way to/from your end-point destination.  Who wouldn’t want two additional vacations for free, right?

4. Don’t be afraid to complain

If you have an issue with your airline or hotel, let them know.  My preferred method is to contact them via Twitter rather than to waste a bunch of time sitting on hold.

Airlines and hotels have pretty broad powers to make things right for their guests… and, as you would expect, they’ll do more when you’re a member of their loyalty program.  I’ve had 4K, 10K, and 50K points recently refunded to my hotel rewards accounts for situations that I’ve had with bugs, for example.

It was said that airlines can generally offer 15-20K miles per issue.  So, if your TV isn’t working properly, your seat doesn’t recline, or there’s some other issue, let the airlines know so they can address them for the next passenger.

The key here is to be nice about it.  Don’t be a jerk.  Think about it… if someone was nice or being a jerk, who would you rather go out of your way to help?

5. You Really Just Had to Be There

Some of the presentations will be released and your friends may share some notes from sessions that they sat in on.  However, unless you were there in person, you won’t necessarily get all the context of what was being shared.

And, if you have a question, there’s no opportunity to ask follow-up questions when you’re reading at home.

Beyond the slides and notes, there is a lot that is said that never makes it out of the room.  Some presenters request that you not take pictures of their slides.  And others share secrets that are so cool that even your friends won’t share because they don’t want it getting shut down.

And, finally, there are tons of inside jokes and “you had to be there moments” throughout the weekend that just don’t translate if you weren’t there.

The Bald Thoughts

Even if you feel that you know a lot about miles and points, it pays to attend conferences like these.  It is awesome to be around people that share the same passion for award travel as you.  And many of the best tips and tricks are shared only in person.  I hope to see you at one of the next travel events!


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