the 14th annual



at Hyatt Regency O’Hare Chicago

the original points and miles event

September 20-22, 2024

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Formerly at the

Holiday Inn

Dive into the heart of the travel community at the 2024 Chicago Seminars (formerly at the Holiday Inn)! Last year, we hit remarkable highs: 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!

To give you a taste of what's in store, last year's schedule follows. This peek into the diverse topics and engaging sessions from our previous gathering will give you an idea of the valuable insights and experiences awaiting you at the 2024 event. Get ready for another year of learning, connecting, and making memories with fellow travel enthusiasts!

2024 Presenters Will Be Announced Soon

2023 Presenters

Special Guest Appearances by:

Tom Stuker - 23 Million Miler with United

Rick Ingersoll - Chicago Seminars Founder

Howie Rappaport - Long-time Chicago Seminars Organizer

Patrick Stouffer - Miles4Migrants


Champagne, Caviar & Showers: Premium Cabin Redemptions

Spencer Howard - Straight to the Points

Going Wild: How to Maximize Frontier’s Subscription Travel Program

Seth Levy - Frontier Fanatic

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

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

Mileage Running isn’t Dead: Learn the Programs Where Trips to Nowhere Will Get You Somewhere

Andrew Kunesh - CNN Underscored & Marty Paz - @MrpAlert

No Flying? No Problem: How to Succeed with AA Executive Platinum Status Without Really Flying

Ashley McCurdy - In Search of Traveler

Ohr Naur, IROPS!: What to Do When a Trip Goes Sideways

Jamie Larounis - @theforwardcabin

Routing Rules: Maximize a Fare's Potential to See More of the World

Ed Sanders - Routing Rule Expert


You CAN Beat the House: How to Make Casinos Work for You

Adam Bauer - @TravelFanboy


Cruise Hacking: Free Cruises, Maximizing Offers, Status Matching & Generating Spend on the Ocean

Shawn Coomer - Miles to Memories

Earning Points & Miles

Big Picture Thinking: Creating Credit Card and Redemption Strategies

Spencer Howard - Straight to the Points

Not Just SUBs: How to Earn a Plethora of Points Without Opening 20 Cards

Julia Menez - @geobreezetravel

General Travel

Binge Traveling to 86 Countries: How You Can Use the Same Approach for Quick Trips

Tippe Morlan - @tippemorlan

Exotic Destinations: Using Points & Miles to Veer Off the Beaten Path

Ryan Smith - AwardWallet

Family Travel For (Closer To) Free: How To Show Your Kids The World While Keeping Your Savings and Sanity

Dia Adams - Fortune Recommends assisted by John Ryan

Insider Information: 10+ Travel Hacker Tips That I Use That I Haven’t Blogged About

Grant Thomas - Travel With Grant

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

Bryan Sklar - TravelWise Advisors

Sensational Solo Travel: Building the Confidence to Travel Alone and Have Fun

Senitra Horbrook - @PointsTravelher

The Wonderful World Of Disney: Proven Tips To Save On Your Disney Vacation

Dia Adams - Fortune Recommends


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

Presidential Suites & Pool Villas: How You Can Procure the Best Rooms Even Without Status

Chris Moss - Suite Connoisseur

Sleep Around: Tips for Maximizing Your Hotel Points

Katie Genter - The Points Guy

Small Footprint but Big Benefits: The Ins and Outs of the World of Hyatt Program

Kathy Kass - Will Run for Miles

Manufactured Spend

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

Jon Nickel-D'Andrea - No Mas Coach!

Excel Between the Sheets: Organizing Your Gift Card Resale Business

Logan Robinson, Ravi Davuluri, Erik Peterson - Aligned Incentives

Reselling and Buyers Clubs: The Good, the Bad, and the Ugly

Shawn Coomer - Miles to Memories

Your Roadmap to One Million Points in a Year: A Step-By-Step Guide to Scaling Gift Card Reselling

Taylor Thomas - QCGC

Technology & Travel

Beyond the Guidebook: How AI and Digital Innovations are Changing Travel Planning

Jackie Wisniewski - Award Travel 101

How Not to Catch a Virus While Abroad: Useful Tech Tips During Your Travels

Kevin Song -

Mindful Travel Photography: Taking More Wow! Photos Through Classic Composition and Lighting

Paul Borish - Travelers Psychological Services

Plan Like an Expert: Tips and Tools I Use to Travel Around the World

JT Genter - AwardWallet


Chicago Seminars, the oldest and largest points and miles travel conference, 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.

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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.

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Lined Corporate SEO Optimization Scene

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.

The submission form will be open until May 31. Selected presenters will be notified by mid-June, but may be notified earlier on a rolling basis, so the earlier you submit the better!

Submit your presentation proposal here.

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)


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


Early Bird pricing is $299 and will increase after May 31.

Please remember prices of goods and services have increased tremendously in the past years.

We have worked diligently to manage costs for this three-day event while providing an excellent attendee experience.

Please remember all organizers and volunteers are unpaid and all profits generated will be donated to charity.


Event tickets must be purchased and include the following:

  • Access to all speaker and panel sessions at host venue
  • 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

There is no hotel room block. Attendees can book directly with Hyatt. You may have further discount opportunities such as 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.