10th Chicago Seminars Registration Now Open – Join Us October 18-20, 2019!

Check out our Top Rewards Cards to boost your points earning and travel more!

Chicago Seminars is back for its 10th birthday, returning to the Holiday Inn Elk Grove on October 18-20, 2019.

Thanks to Howie Rappaport for again putting this together, and all the volunteers that make this possible, affordable, and fun. For the big 10th, event founder Rick (ingy) will join the festivities.

Chicago Seminars 2019About 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 usually arrive via an international road trip. This year my arrival will be straightforward. For my departure, I’ll stay over Sunday (join me for post event happy hour!) and Monday I’ll be on a madcap national parks, presidential libraries, and UNESCO sites drive to St Louis by way of Indiana.

My sessions are:

  • Points to Islands – The World’s Most Incredible Islands and How to Get Yourself to Them
  • Credit Cards Level 999
  • Ask Me Anything, where I’ll be Joined by new speaker and ‘zero to MS hero’ Zach Finkelstein
  • Sunday Credit Card Panel
  • Event Closing Free-for-all-Panel


The whole weekend including lunch both days is $125, register here.

The host hotel room block is $115/night and includes breakfast for 2, book here (link only works on desktop browser, not mobile, blame IHG, not Howie).

Attendees choose to stay all over the area, some even mileage run each night staying in different cities. 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.


Friday early arrival sessions are a great start. 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 (Howie) – 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

50 ways to earn miles, points, & cash back without a new card (Lee Huffman / BaldThoughts.com)

Sweet Spots & Maximization with Hotel Points (Henning Mente / First Class & More) – 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.

Non Rev – Good, Bad, Ugly (Dave H / Bikeguy) – A peek behind the curtain of those seats that get filled at the last minute by airline employees, their friends, family, and buddies.

730pm – 830pm

Fly 9 people on the same award flight almost every time – Sweet Spots! (Richard Kerr)

Case Study: I went from MS idiot to earning 500K points in a month (Zach F) – How to become an MS expert in 1 year.

Maximize Las Vegas/Hotel Loyalty Crossover – (Bethany Walsh / Bougie Miles) – Strategically Combine perks like Amex’s FHR Benefit with casino offers and hotel loyalty programs for big benefits, cheap rooms, and lots of points


8am – 12pm – Registration Desk Open

830am – 930am – Credit & Rewards Cards – History Lesson, How Things have changed, and where we are now. (Howie & Rick) – Howie and Rick will cover the fundamentals of credit, credit scores, and dispel some of the too many myths with credit cards. Are you under 5/24? Should you care?

945am – 1045am

Awards worth MSing for (Nick Reyes / Frequent Miler) – The top 2 sweet spots from each major transferable currency analyzed in terms of cost to MS under normal circumstances. From amazing deals on domestic travel to round-the-world in luxury and style for less than you might expect.

Points to Islands – The World’s Most Incredible Islands and How to Get Yourself to Them (Stefan / Rapid Travel Chai) – Napoleon on St Helena, GIs on Guadalcanal. Dragon’s Blood Trees of Socotra, wombats of Maria Island. Beaches beyond belief and all to yourself. Encounter the world’s most incredible islands and how to make your island dreams a reality with points.

My 2.5 Month Family Trip (Shawn Coomer / Miles to Memories & DisneyHacks.com) – Planning, Redeeming, and the Highs/Lows of 70+ days away on the move with the family.

11am – 12p

New to the game: Understanding award charts, partner airlines, and transferring your points and miles (Tiffany / One Mile at a Time) – How do you know how many miles you need for an award? How do you book an ANA award with United miles or a Delta award with Virgin Atlantic miles? Get the basics for how to figure out what you need and book partner awards.

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.

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.

12pm – 1pm – Lunch

1pm – 2pm

Panel on Disney (Dia, Shawn, Richard, and Marty) – 4 completely different perspectives from some of the nerdiest points and miles Disney nerds. Come with your crazy questions.

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!

Outside the Box (Henning Mente / First Class & More) – Discover the world of loyalty away from credit cards and the big US airlines and hotels. You will get a bunch of ideas to improve your travels with foreign and lesser known miles and points programs.

215pm – 315pm

All the apps you need on your phone to save money on everything (Richard Kerr) – Got a smartphone? Richard will show you all the apps you should be using to save money — on everything. Oh, he’ll show you how to do a sextuple (6x) dip on earning.

#40kfaraway with Frequent Miler (Greg & Nick / Frequent Miler) – Lessons learned from a challenge to get as far away as possible on 40K points and $400.

Maximizing Air France Flying Blue (Spencer / Straight to the Points) – One of a few programs that deserve a dedicated session. Transfer partner from so many programs, you can’t ignore Flying Blue

4pm – 5pm

Ask Me Anything / Why You’re Doing it Wrong – Dispelling Group Think in the Points/Miles World (Richard Kerr) – 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 Frequent Miler (Greg / Frequent Miler) – You’ve got questions, Greg has answers.

How Miles & Points Led Me to Quit My Job and Move To Nashville (Lee Huffman / BaldThoughts.com)

515pm – 615pm

Buying into Buyer’s Groups (Zach F) – How you can join buyer’s groups — effectively, buying electronics for a large group and earning points — as well as tips on how to be smart about the process (how to keep good records, importance of reconciling, ways to network and find more groups).

Loyalty Program Elite Status Without the Loyalty – (Bethany Walsh / Bougie Miles) – Easiest ways to obtain elite status in airline and hotel programs and maximize the value of your perks.

Group Award Travel – 5+ people (Dave H / Bikeguy) – You need to be creative when it comes to adding a 3rd, 4th, or 5th person to your travel group. If you thought finding 2 award seats with tough, learn how to make larger group travel work out.

615pm – 7pm

Ask Me Anything with Stefan and Zach — Credit card or MS question? You’re welcome

7pm – 8pm

Happy Hour / Reception in Woodfield Ballroom

SUNDAY OCTOBER 20TH (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 – Airline Breakouts – Large Roundtable discussions for major airline programs – Pick your favorite and participate in an informal discussion (AA, Delta, United, Southwest, Everyone Else)

1215pm – 115pm – Lunch

130pm – 230pm – Hotel Breakouts – Large Roundtable discussions for major hotel programs – Pick your favorite and participate in an informal discussion (IHG, Hyatt, Marriott, Hilton, Everything Else)

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

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3 years ago

Went twice and they felt like I was back in high school with everyone huddled around the “popular” peoples during the bar and breakout sessions. It was far too cliquish for my taste. Add in the weak lineup of speakers this year and it’s a hard pass.