the 14th annual



at Hyatt Regency O’Hare Chicago

the original points and miles event

September 20-22, 2024

Green Sale Banner

Formerly at the

Holiday Inn

Dive into the heart of the travel community at the 2024 Chicago Seminars (formerly at the ​Holiday Inn)! We hit remarkable highs last year: over 300 attendees, 37 enlightening sessions ​from 29 expert presenters, and a generous $17,000 donated to charity!

This isn't just an event; it's a convergence of enthusiasts eager to share, learn, and elevate their ​travel game—all while making a meaningful impact.

In response to our attendees' feedback for a more upscale and convenient venue, the 2024 event ​is excitedly making its move to the Hyatt Regency O'Hare. This new location not only meets our ​community's growing needs but also elevates the overall experience with its top-notch facilities ​and services. Perfectly situated with easy airport access, the Hyatt Regency O'Hare offers a ​sophisticated backdrop for our sessions, networking, and festivities. Experience the blend of ​luxury and convenience at our new home which promises to make the 2024 Chicago Seminars an ​unforgettable event!

Get ready for another year of learning, connecting, and making memories with fellow ​travel enthusiasts!


Chicago Seminars, the oldest and largest event for the ​points and miles community, was founded in 2010 by ​Rick Ingersoll and Win Schaeffer then nurtured by long-​time organizer Howie Rappaport. Since that time, ​Chicago Seminars has blossomed into the premier event ​for sharing knowledge and strategies on maximizing ​points and miles. With a steadfast focus on community ​and connection, Chicago Seminars has empowered ​countless travelers to bring their travel aspirations to ​life.

While there are similar points and miles events, Chicago ​Seminars is unique in that it is a registered non-profit ​and 501(c)(3) under the direction of a volunteer board. ​All organizers and volunteers are unpaid, and all profits ​generated are donated to charity.

Lined Corporate SEO Optimization Scene
Lined Corporate SEO Optimization Scene

Featuring a dynamic lineup of keynote addresses, breakout sessions, panel discussions, and networking activities spanning three days, in 2023, more than 300 participants, ranging from novice adventurers to seasoned points and miles experts, took part in 37 sessions led by 29 presenters. This annual gathering of the award travel community also raised more than $17,000 to support our charity partners.

For more than a decade, the original points and miles event has played a key role in the award travel community by fostering in-person connections which create meaningful and lifelong friendships from around the world. We look forward to you joining us and sharing your experiences at this Chicago homecoming.

Lined Corporate SEO Optimization Scene
Lined Corporate SEO Optimization Scene

2024 Sponsors

Each year, Chicago Seminars is delighted to have a fantastic array of sponsors. Sponsorship ​packages can be personalized to suit any needs.

If you would like to sponsor for 2024, or know a person or business which might want to be a ​sponsor, please reach out to

2024 Presentations

Lined Corporate SEO Optimization Scene

Encore Seminars

We are delighted to announce we will be revisiting some of the most highly acclaimed ​sessions from the previous year. These sessions, as per the feedback received from attendees, ​were rated almost flawlessly by all participants. We extend our heartfelt gratitude to the ​speakers for delivering such captivating, insightful, and informative presentations.

Feature Seminars

Feature Seminars will be of interest to a broad audience. Experts will discuss topics from how ​to use new award search tools, renting a castle for your family, and starting your foray into ​manufactured spend. We even have sessions for penguin lovers and Swifties.

Express Seminars

New for this year are Express Seminars. Express Seminars are shorter sessions on topics ​specific attendees will find interesting, such as how to earn points on wedding expenses, ​keeping your P2 engaged, and even how to land a plane.

Community Seminars

Chicago Seminars is about more than just points and miles; it’s about connecting people with ​an interest to travel the world. Community Seminars will not only help you foster connections ​with fellow travel enthusiasts but will provide you with tools to maximize the value of the ​weekend.

Lined Corporate SEO Optimization Scene
Lined Corporate SEO Optimization Scene
Lined Corporate SEO Optimization Scene
Lined Corporate SEO Optimization Scene

Encore Seminars

Special Presentations

Life as a 24 Million Miler: Insights from the World's Most Travelled Man

Tom Stuker: @ua1flyer


How to Fly Anywhere: The Value of Alaska Airlines Mileage Plan

Ben & Jon Nickel-D'Andrea: No Mas Coach!

Points or Cash - Why Choose?: Get the Most Bang for Your Buck (Or Points) in Your Travels

Bryan Sklar: @travelwiseadvisors


You CAN Beat the House: Making Casinos Work for You

Adam Bauer: Cheapskate Vegas

Earning Points & Miles

Hardbody, the Plastic Merchant, Dogs with Credit Cards & Other Dumpster Fires: Deals Gone

Wrong & Deciding When to Say No


General Travel

Beyond the Guidebook: How Ai and Digital Innovations Are Changing Travel Planning

Jackie Wisniewski

Plan Like an Expert: Tips and Tools for Global Travel

JT Genter: @jtgenter

Traveling as A Woman: Advice from Female Globetrotters



Family Travel for (Closer To) Free: Showing Your Kids the World While

Keeping Your Savings and Sanity

Dia Adams: Fortune Recommends

Sleep Around: Maximizing Your Hotel Points

Katie Genter: The Points Guy

Manufactured Spend

Amazon FBA, Reselling, and MS: What You Need to Know

Jon Nickel-D'Andrea: No Mas Coach!

Feature Seminars


Are They All the Same?: A Comparison of AIRLINE Award Search Tools


Around the World in 80K Miles (Not Days): How to Book RTWs with ANA


Consistency Is Key: The Most Fail-safe Award Travel Sweet Spots

Julia Menez: @geobreezetravel

The Best of the Best: Comparing Aspirational Airline Products

Panel hosted by Han Chicago: @hanchicago


Roll Your Windows Down and Cruise: Sometimes for Free!


Earning Points & Miles

Living the High Life: Secrets to Jet-setting Around the Globe for Free

Ronnie Dunston: @ronniedunston

Points & Credit Card Perks You Are Overlooking: Business Cards and How Owners (And ​Non-Owners) Can

Earn Lots of Points

Ryan Smith: @ryansmithtravel

Prioritize Your Time While Maximizing Your Rewards: An Unorthodox Approach for Travel ​Hackers

Chris C.: @married_withpoints

We're Not in Kansas Anymore: Life Beyond 5/24

Shira Sliffman : Travel on Point(s)

Will You Be Approved?: Preparing for Your Credit Card Applications

Arthur Chow: @the.arthur.chow

General Travel

(e)Sims in the City: Cell Phone Use Outside Your Home Country

Kevin Song:

A Must Before You Go: Travel Insurance

Pamela Scala

More Magic for Your Miles: Disney Vacation Strategies Around the World

Leslie Harvey: Trips with Tykes

Once in a Lifetime?: Trips to the Olympics and Antarctica


Save Your Points: Crafting Cheap Bucket List Itineraries

Carissa Rawson: @just.plane.points

The Fringe Are Your Friends: Why Hyatt, Marriott, Hilton, IHG, United, AA, and DL Suck ​(You In)

Joseph Petrovic: Award Travel 101

“It’s Been a Long Time Coming”: Seeing Taylor Swift in “Style” 7 times on Multiple ​Continents for Cheap

Kevin Song: & friends

When to Buy Points & Miles: Using Cash to Upgrade Your Travels

Miguel Rueda: @travelsergeant


Sponsor Session: The Benefits of Award Search Tools by

Are They All the Same?: A Comparison of HOTEL Award Search Tools


Presidential Suites & Pool Villas: Securing the Best Rooms Without ​Status

Christopher Moss: @chrismoss7

The Hidden Value of Hilton Honors: from Zero to One Million Points for ​Luxury Hotel & Resort Redemptions

Amanda Keane: @amanda.exploring

Manufactured Spend

Buyers’ Clubs: The Good, the Bad, the Ugly


Fluz, Taekus, Bank Bonuses, Etc.: Non-traditional Ways to Earn More ​Points Panel

How to Scale & the Art of the Stack: Points, on Top of Points, on Top of ​Points

Todd Evans: Disability Parenting

Manufactured Spend with Online Gambling: Integrating MS and Earning ​Other Benefits

Justin Vacula: Hurdy Gurdy Travel Podcast

MS Starter Pack: Zero to Hero with Manufactured Spending

Anthony Garritano

Additional Feature Seminars

Elina Geller: @themissmiles

Spencer Howard: Straight to the Points

Express Seminars


Behind the Scenes at Airlines: Tales of IROPS Management from an Air Traffic Controller

Craighton Miller: @craighton

Benefits of Airline Status Matching: Unlocking Additional Perks

Marty Paz: Notiflyr & Seth Levy: @sethlevy

How to Land A Plane: Pilot Stuff You Know You Want to Know

Kevin Song: & Brandr Beekman-Ellner: @brandr.beekmanellner


The Status Matching Merry-go-round: Turning Gambling Into a Travel Strategy

Dave Grossman: MilesTalk

Large Expenses

Make Wedding Expenses Work for You: Turning Big Costs into Big Rewards

Brian Cohen: Award Magic

Maximizing Your Miles While Paying for College: Turning Tuition into Travel

Basil Karampelas: @bigspendbasil

Quick Travel

Binge Travel: How to Maximize Your Trip Experiences

Tippe Morlan: @tippemorlan

Layover Life: Making the Most of Your Extended Stopovers

Mike Zaccheo : Award Travel 101


Building Bridges: Getting Your Reluctant P2 to Help More

Ryan Smith: @ryansmithtravel

Starting Out

Back to Basics: Terms You Hear About but Don't Understand

Ryan Smith: @ryansmithtravel

Raising Globalists: Gen Z and Starting Travel

Emilia I. Rutigliano:

Community Seminars

Full Circle Award Travel: Building Friendships in the Points & Miles Community

Joseph Petrovic: Award Travel 101

The Art of Persuasion: Cultivating Friendships at Travel Conferences

Ben Komenkul: Ben’s Big Deal

The Value of Relationships: Building Connections in the Points and Miles Community

Jason Dimaio: @jdimaio

What I Wish I Knew Way Back When: Tips from Experienced Travelers

Toni Perkins Southam: @tonisoutham

Who Are These Points & Miles Fanatics?: A Survey of the Community

David Ocamb: The Ocamb Group

Tentative Schedule

Friday, September 20, 2024

3:00 PM: Registration Opens

5:30 PM: Opening Remarks

6:00 PM: Friday Night Sessions

8:30 PM: Reception (One drink included)

Saturday, September 21, 2024

7:30 AM: Registration Opens

8:00 AM: Saturday Morning Sessions

12:00 PM: Saturday Lunch (Included)

1:00 PM: Saturday Afternoon Sessions

6:30 PM: Dinner (Not included)

8:00 PM: Chicago Seminars After Dark (Add on)

Sunday, September 22, 2024

8:00 AM: Sunday Morning Sessions

12:00 PM: Sunday Lunch (Included)

1:00 PM: Sunday Afternoon Sessions

4:00 PM: Closing Remarks

5:00 PM Late Night Flight Hang – at Airline Lounges or Hotel Bar (Not included)

Call for Presentations

Chicago Seminars is proud to be a community-run event. This year, in addition to ​our usual docket of phenomenal presenters, we’re opening the door and inviting ​YOU to submit presentations for consideration.

You do not need any prior speaking experience and all are welcome to apply. If ​you have a topic you think would be interesting, but aren’t the right person to ​present, submit your suggestion and we’ll find a presenter for it.

2024 Submissions closed May 31st. A big THANK YOU to those who submitted ​presentations and ideas!


On June 1, the cost of a General Admission ticket ​changed fro $299 to $329. On August 20, the ​price will increase to $359.

A new After Dark event is available for $30 and ​must be purchased with a General Admission ​ticke​t​.

Please remember prices of goods and servi​ces have increased tremendously in the past year​s​.

We have worked diligently to manage costs ​for this three-day event while providing an excell​ent attendee experien​c​e.

Please remember all organizers, speakers, ​and volunteers are unpaid and all profits genera​ted are be donated to charit​y.


General Admission tickets include the following:

  • Access to all Encore, Feature, Express, and ​Community Seminars
  • Lunch on both Saturday and Sunday
  • A complimentary drink at the Friday night ​Reception

There is no virtual option and sessions will not be ​recorded.

Although registration is nonrefundable, ​registration is transferable for a $25 fee and ​must be completed by Monday, September 16, ​2024. Email if you ​would like to transfer a ticket.

Important Policies

Since the first Chicago Seminars, we have had ​the following policies, and by attending, you ​agree to such:

  • Tickets are nonrefundable but are ​transferable for a $25 fee
  • No chargebacks on tickets
  • If you break any of the terms or are asked to ​leave by the organizers for any reason, you ​will not be allowed to attend any future ​events

Sponsorship Information

Sponsorship packages start at $1,000 and can be personalized to suit any needs.

Please email if you would like to be a sponsor or if you know a person or business which might want to be a sponsor.

Travel Information


Hyatt Regency O’Hare Chicago

9300 Bryn Mawr Avenue

Rosemont, IL 60018

+1 847 696 1234

Hotel Booking

Rooms can be booked for 8,000 Hyatt points. ​Attendees can also book directly with Hyatt and ​may have further discounts via AAA, AARP, ​Leverage rates, etc.


Chicago O’Hare (ORD) is the closest airport to ​the Hyatt Regency Chicago O’Hare. The hotel ​runs a shuttle to and from ORD every 15 minutes. ​Chicago’s Midway Airport (MDW) is far and no ​transportation is provided. Public transportation ​or ridesharing can be used from Midway Airport.

Charity Raffle & Auction

Through the years, Chicago Seminars has raised tens of thousands of dollars for charitable organizations through its Charity Raffle & Auction. 100% of these proceeds go to charity. We will share our 2024 Charity Partners soon.

Both travel- and non-travel-related items are being sought for the Charity Raffle & Auction. If you have items to donate, bring the item(s) with you to the event. No value is too small. Raffle tickets can be purchased via credit card and you do not have to be present to win.

If you have a larger item or experience to donate, please email

Volunteer Opportunities

It takes a village to run an event such as this, and your help is still needed, especially during the event. If you would like to assist, please email Volunteering does not provide a complimentary registration.

Etiquette and Rules

This is a volunteer event for the points and miles ​community. Each attendee is expected to be ​respectful during all official and non-official ​events. The following are a few rules that need to ​be expressed at each event as they are ​particularly important:

  • Recording any presentation in any way is not ​allowed without advance explicit permission ​from both the event organizer and presenter. ​Violators will be immediately dismissed ​without refund. This policy respects the ​presenters’ content and allows open ​discussion of topics, some of which are ​intended to not be made public.
  • The purchase of a ticket requires acceptance ​to all terms and conditions stated during the ​ticketing process including, but not limited ​to, liability of any kind.

Closing Thoughts

Please remember this event is organized by unpaid volunteers. If you have a serious and immediate concern, ask to speak to one of the main organizers immediately.