Chicago Seminars 2017 Registration and Hotel Booking Now Open

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Chicago Seminars is back for its 8th year, returning to the Holiday Inn Elk Grove on October 20-22, 2017.

Chicago Seminars 2017

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. I’ll be presenting on:

  • Advanced Credit Cards
  • 101 Tips, Tricks and Hacks to be an Expert Travelers
  • Moderating our event closing free for all panel

All of us speakers volunteer for the event.


Registration kicked off last week and now the hotel block is available. Staying on-site is convenient. Alternatively, there are many nearby hotels for your mattress run/points promo de jeur.

The event is $105, register here.

The room block is $94/night and includes a basic breakfast, book here.


This year there are even more Friday early arrival activities. Saturday is packed with lectures. Sunday is breakout sessions.

The full schedule is:


2pm – 3pm – Pre-Registration Small Group Credit Card Discussions. These small group breakouts will be moderated by some of our speakers who have volunteered extra time to spend chatting about credit cards and reward strategies. You don’t need to register for this now, however, prior to the event, a survey will be sent out to inquire if you’re interested in participating. We want to make sure we have enough people to cover so we can keep the groups small.

4pm – 8pm – Registration Desk Open

5pm – 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

Introduction to Manufactured Spending (René / RenésPoints) – A beginners look answering the questions What is Manufactured Spending? What are the different types, risks, and rewards of “MS”? Can this help me travel for less?

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. This seminar will also include a brief question and answer session near its conclusion.

Booking Travel for Five or More (Dave / Bikeguy on FlyerTalk) – When you’re a solo traveler or a couple looking to cash in miles you often have struggles with finding just the right flights … but what about trying to make it happen for five or more people?

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. This seminar will also include a brief question and answer session near its conclusion.

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.

Ask Me Anything with Howie from AwardWallet (Howie / AwardWallet) – Not nearly as smart as Tiffany, but Howie knows a thing or two about managing credit cards and rewards programs for large groups of people (e.g. his extended family and clients)


8am – 12pm – Registration Desk Open

830am – 930am – Using Points & Miles to get to Necker Island (Greg / Frequent Miler) – Greg wasn’t able to make it to the Chicago Seminars last year, he and his wife were busy hanging out with Richard Branson on Necker Island — all done with points. He’ll tell his story and hopefully inspire you to up your commitment to points and miles.

945am – 1045am

Advanced Credit Cards (Stefan / Rapid Travel Chai) – Banks are getting 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 manufactured spend, and more.

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.

Kimpton Hotels: The Most Rewarding Hotel Loyalty Program You’ve Never Heard Of (Lee / – With programs merging and benefits being slashed Kimpton stands tall at providing some of the most (if not THE MOST) rewarding benefits of any loyalty program out there. If you like fantastic hotels and even better service, this could be your hotel loyalty program of choice.

11am – 12p

Unique Award Redemptions (Richard Kerr / Travel Hacking 101) – Covering award redemptions including Noumea to the 5 stopovers and 2 open jaws of Asia Miles. This seminar will have a specific focus on allowed routings of lesser-studied transfer partners and even some of the most well-known programs people over look.

Introduction to Reselling of Gift Cards and Merchandise (Shawn Coomer / Miles to Memories) – One of the most lucrative ways to accumulate massive amounts of points and miles is through product reselling. Whether you’re buying/selling through Amazon or through gift card resellers, merchandise arbitrage can help build you a hefty balance in your travel bank and at the same time open an opportunity to make some cash and easily meet any minimum spend requirements.

Airbnb Tips & Hacks (Scott Grimmer / Mile Value) – Scott stays with Airbnb almost 300 days a year. If you want some good advice on picking the right Airbnb, saving money, and negotiating price this is for you.

12pm – 1pm – Lunch

1pm – 2pm

Sweet Spot Award Redemptions (Scott Grimmer / Mile Value) – Whether you dream of a huge, round-the-world trip or just want to find the best use for each of your mileage balances, you need to know the sweet spots on each miles’ award charts. This presentation will cover some sweet spots with United, American, Delta, Alaska, Singapore, Korean, Flying Blue and many more miles. Plus there will be example itineraries that string together several miles’ sweet spots into amazing trips.

Expert Reselling of Gift Cards and Merchandise (Shawn Coomer / Miles to Memories) – This session is NOT for the beginner. You should have experience in reselling as the basics won’t be covered. Learn how to scale your operation properly, and maximize your return with reselling. Looking to make it a full-time operation? This is for you.

Maximizing Hotel Best Rate Guarantees (Angelia / Angelina Travels) – Just because you’ve found the right hotel and an OK price, doesn’t mean your work is done. Is it the best price? Can you get a better deal through an obscure site? What about if the rate drops? Knowing the tips and tricks to maximize hotel program best rate guarantees can save you hundreds with minimal effort!

215pm – 315pm

101 Tips, Tricks, and Hacks to be an Expert Traveler (Stefan / Rapid Travel Chai) – A fun, practical romp through the world of travel in 101 tips from miles and points to what to do on the road to be an expert traveler. If you’ve never had a layover in a Japanese love hotel, this session is for you!

Sustainable and Enriching Family Points and Miles Strategies (Richard Kerr / Travel Hacking 101) – Richard shares everything he considers as a traveling family of four on how to get the most points and miles and get the most out of his points and miles. He’ll share the backpack on top of a diaper bag with a baseball cap trick to make people think the Southwest seat is full and discuss how to strategically book the same flight with different programs so you can protect yourself in case of delays and cancellations.

Honeymoon Destination: Earth (Nick Reyes / Frequent Miler) – How a year of collecting miles and connecting dots led to a 4-month honeymoon around the world and how you can plan the ultimate romantic getaway — whether to beautiful beaches or off the beaten track.

4pm – 5pm

Greatest Deals and Promos of All Time and How to Evaluate a Deal (Dave / Bikeguy on FlyerTalk) – A combination of a trip down memory lane and how to quickly evaluate a deal to determine whether to participate and at what level. Dave will cover why always having a calendar with open weekends or weeks available can be a big benefit. He’ll tackle the effort versus reward challenge, how fast a deal is likely to get pulled, and your tolerance for risk. Lastly, he’ll cover not taking anything for granted — if a deal is there, you have to take advantage of it now because it probably won’t be there tomorrow.

Ask Me Anything with Frequent Miler (Greg / Frequent Miler) – Greg is an expert on how to pick up mass amounts of points and miles without setting foot on a plane or spending a night in a hotel. Spend an hour picking his brain where you can ask him anything — maybe he’s headed back to Necker?

How to Maximize Hotel Points with Category 1 and 2 Redemptions (Dan / Points with a Crew) – It seems that many folks talk about how they stay for free in 5-star hotels using miles and points. And while that is one way to travel, did you know that in some programs, you can get up to 20 nights at a lower level hotel for the SAME amount of points as 1 night at a top-tier hotel. And we’re not talking about roach motels here – these can be some pretty nice places! Learn how to maximize your hotel points with Category 1 and 2 redemptions.

515pm – 615pm

Cards with Benefits (Nick Reyes / Frequent Miler) – Rewards-earning cards are much more than the points and miles associated with them. Nick will review everything about leveraging your card’s ancillary benefits to get an outsized value to save you time and money.

You Can Fight Citi Hall: Lessons From a Shutdown and Arbitration (Eddy) – A real example and experience from one of our own who just concluded an adventure battling Citibank after they closed his four credit card accounts, bank accounts, and ThankYou points account confiscating about 500,000 ThankYou Points. You’ve got always to keep your head in the game, and if you want some lessons learned about what matters to the biggest reward currency providers out there, this is for you.

Avoiding shutdowns / Financial Reviews and Customer Services levels (René / René – Want to avoid having your rewards confiscated? Don’t want to spend time providing tax returns and reviewing your financials with the banks? You should listen to what René has to say.

7pm – 8pm

Happy Hour / Reception in Woodfield Ballroom

SUNDAY OCTOBER 22ND (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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5 years ago

Is there an overflow hotel?

5 years ago

Looking forward to attending for 4th year running. Always like hearing your talks Stefan, and the other bloggers too of course. And it’s good to hear the charity $ total donated afterward too. Any idea who the charitable organizations will be this year?

Stefan @ Rapid Travel Chai
Reply to  dmat

I have not seen it announced on the event’s thread yet.

See you in Oct.

5 years ago

I meant glad you are back

Stefan @ Rapid Travel Chai
Reply to  Shannon

Been very busy on the home front. I am back.

5 years ago

glad you are black. I was worried you gave up this blog

Stefan @ Rapid Travel Chai
Reply to  Shannon

Not either.