Get Yourself to Chicago Seminars October 19-21

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The case for me to attend miles and points conferences is this: every key relationship I have made in this hobby has either come from conferences and meetups or been strengthened by them.

Putting a face and a handshake to an online name matters a lot. The people who are dismissive of this from their Slack and Telegram channels are missing out.

Chicago Seminars is the most interactive, community-feeling miles and points conference. Back for its 9th year, we return to the snug confines of Holiday Inn Elk Grove on October 19-21, 2018.

Thanks to Howie Rappaport for again putting this together, and all the volunteers that make this possible, affordable, and fun.

About Chicago Seminars:

Chicago Seminars is largest and longest-running miles and points conference. There is an energetic mix of veterans and rookies. Sessions cater to all skill levels.

I am excited to be back to join a great program.

In my tradition of having a pre-event road trip to make Howie worry if I’ll turn up, I’ll be off a cross-Turkey drive from Lake Van to Istanbul.

My sessions are:

  • Advanced Credit Cards
  • Ask Me Anything
  • Moderating our event closing free for all panel


The whole weekend including lunch both days is $111, register here.

The host hotel room block is $109/night and includes breakfast for 2, book here.

Attendees choose to stay all over the area, though the most fun is had by people at the host hotel who can more easily participate in the nearly round-the-clock socializing and networking. I recall one year around 3 am several heavy volume resellers were still in the lobbying banging away at an eBags deal.


Friday early arrival sessions at great. Saturday is packed with lectures. Sunday is breakout sessions.

The full schedule is:


4pm – 8pm – Registration Desk Open

530pm – 6pm – Welcome to Chicago Seminars & Tips on a Successful Event (thehowieee / AwardWallet) – An Introduction to the Chicago Seminars, some tips on how to get the most out of the weekend and an open forum to ask any event-related questions.

615pm – 715pm

Renting Cars for Profit & Elite Status (J.J. / Easy Go Traveler & Marty) – These guys accumulated over 2 million miles last year through rental car promotions. If you want to learn from two people that think outside the box, this is for you. They’re pros in way more than just rental cars. See the TPG article on J.J.

Maximizing your points with 6 airline partners from Asia (Spencer / Straight to the Points) – Learn great ways to use ANA, JAL, Asiana, Korean Air and Asia Miles. Spencer will cover key / unique aspects of the programs such as stopovers, routing, things that can easily confuse while at the same time increase the value of the miles immensely.

Booking your first award (Tiffany / One Mile at a Time) – The fundamentals needed to book your first award ticket, including understanding alliances and partnerships, general tactics for finding award space, and what to expect when it’s time to use your miles.

730pm – 830pm

Mattress Running for Hotel Status & Promotions (John / laptoptravel) – This seminar will show you how to identify opportunities to capitalize on hotel promotions to maximize your return on investment. This seminar will also teach you how to plot and plan a systematic approach to a mattress run. As an example, I will share my personal example of 16 stays in 16 nights; with no consecutive nights at any property. This seminar is for anyone that is willing to put in some time to research and put together an action plan for success. No prior knowledge or experience with mattress running is necessary. I will share with you insight on where to identify opportunities to achieve and maintain hotel elite status and quantify the true costs of getting and keeping that status.

Leveraging Vacation Rentals – Hotels Don’t Always Make Sense (Dia / The Deal Mommy) – Do you find yourself often need more space than a single hotel room affords, or the price of a hotel is insane, or you just don’t want to stay in a cookie cutter place — vacation rentals can help with all of these. Dia thinks outside of the box without compromising quality and helps you spend your money perhaps where you’d rather see it go.

Making Memories with Photos – More than an iPhone (Toni Perkins Southam / Award Travel 101) – Toni’s photo skills are insane. She’s using more than her iPhone but if you want to make some amazing memories with your photos, spend an hour with her to learn how to do it right.


8am – 12pm – Registration Desk Open

830am – 930am – Credit & Rewards Cards – How to do it right (Howie / AwardWallet) – Howie will cover the fundamentals of credit, credit scores, and dispel some of the too many myths with credit cards. Are you under 5/24?

945am – 1045am

Miles & Points for Beginners (Emily / Million Mile Secrets) – Emily will cover the foundational principles that everyone should follow to be successful with points and miles.

Top 10 Frequent Miler Insider Tips (Greg / Frequent Miler) – Greg will cover his top 10 tips not discussed on the blog.

Travel Photography – Great Pictures Without a Ton of Equipment (Jeff Brownson) – Going light on equipment and still coming home with amazing photos. An iPhone and a couple of attachments can be all you need to carry. Also, how to edit in just a few seconds to make your social media pictures look much better.

11am – 12p

Ask me Anything with Frequent Miler (Greg / Frequent Miler) – You ask, Greg answers for 1 hour.

Disney Disney Disney with Dia (Dia / The Deal Mommy) – You either get Disney or you don’t. If you have a love for Disney and want to do it right (no lines, better prices, less pain), you have to attend this session.

Status Matching & Maximization (Henning Mente) – Only the beginning is hard. Learn the skills and which programs from airlines, hotels, and car rental companies are worthwhile applying a match.

12pm – 1pm – Lunch

1pm – 2pm

Earn Miles Without Flying: Ways to build your balances without Manufactured Spend (Nick Reyes / Frequent Miler) – Subject says it all. Nick will cover how to spot deals and focus on out of the box ways to rack up tons of points and miles

Advanced Mileage Run Techniques (John / laptoptravel) – Beyond the simple hit & miss or ‘fare alerts’ a hobbyist might stumble upon, this session will provide some rarely shared techniques to make Mileage Run discoveries more efficient and productive. This seminar is not for the inexperienced; it is best if you come with some knowledge of using either Kayak or Priceline Multi-City Booking Tools, ITA Matrix or comparable first-hand experience in constructing your own Mileage Runs. I will share with you some insight on how to tweak even other’s fare alerts to meet your needs or improve upon the rewards. I will share a couple of my own Mega Mileage Run examples to the participants.

Maximizing Layovers (Jeff Brownson) – Jeff will cover challenges with undesirable layovers, how to maximize them to your benefit. He’ll cover ways to store luggage, renting cars, and leveraging hotels for the quick stays. He’ll cover his own personal experience to give you ideas on how you can easily add a layover on your trips.

215pm – 315pm

Why You’re Doing it Wrong – Dispelling Group Think in the Points/Miles World (Richard Kerr / Award Travel 101) – Don’t be a robot and believe just what you see. Think outside the box, think through an idea and don’t follow what everyone else does. Richard will go over examples of how and why you need to think differently and how to beat what everyone else is doing.

Ask Me Anything with Tiffany from One Mile at a Time (Tiffany / One Mile at a Time) – Looking for a chance to get YOUR question answered by an expert in every aspect of the points and miles world? (she won’t admit to it, but she is). Bring your out of the box questions to try and stump Tiffany — good luck!

Ask me Anything with J.J. & Marty (J.J. / Easy Go Traveler & Marty) – An hour to ask two guys that spend their days maximizing promotions how they do it, why they do it, and how you can do it.

4pm – 5pm

Advanced Credit Cards (Stefan / Rapid Travel Chai) – Banks are smart, so we need to be smarter. Learn the latest developments and techniques for maximizing credit card rewards and benefits. Explore little-known cards, cards for heavy spend, and more.

Maximizing Citi ThankYou Points (Spencer / Straight to the Points) – The Most Underrated Flexible Points Program out there, Spencer will show you how to extract maximum value and convince you that you shouldn’t be ignoring TYP.

Sweet Spots & Maximization with Hotel Points (Henning Mente) – A lot of hotel programs had a relaunch or changed their conditions: World of Hyatt, SPG/Marriott Rewards/The Ritz-Carlton Rewards merging and Hilton Honors changed the rules. In this session, Henning will give an overview of the most generous programs, the best quick wins for beginners, how to get a high tier elite status fast and how to get a maximum value out of your points.

515pm – 615pm

Airline Award Sweet Spots (Richard Kerr / Award Travel 101) – The sweet spots that aren’t obvious. Richard obsessively studies airline award charts and award zones to figure out how any award can be maximized. Which program to use when, how to find the best value, and how to never say “I should have used these miles instead”

#FAIL : The mistakes I’ve made in this game and what you can learn from them (Nick Reyes / Frequent Miler) – From resales gone wrong to redemptions I regret and all the miles I’ve left on the table — Nick will go over what you shouldn’t do and how to avoid making those same mistakes.

Ask me Anything with Stefan from Rapid Travel Chai (Stefan / Rapid Travel Chai) – In addition to knowing an insane amount about credit cards, Stefan is a handful of countries short of visiting them all. Anything travel relayed, he’s your guy.

7pm – 8pm

Happy Hour / Reception in Woodfield Ballroom

SUNDAY OCTOBER 21ST (All Sunday Sessions are open to all)

8am – 9am – Open Panel Discussion on Credit Cards

9am – 10am – Sponsors Workshop

10am – 11am – Charity Raffle

1115am – 1215pm – Hotel Breakouts

1215pm – 115pm – Lunch

115pm – 230pm – Airline Breakouts

245pm – 4pm – Event Closing & Open Panel on Everything Else Moderated by Stefan / Rapid Travel Chai

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