the 13th annual

chicago seminars @the holiday inn

the original points and miles event

October 13 - 15, 2023

Register for 2024 soon!


Founded in 2010 by Rick Ingersoll (aka Frugal Travel Guy), Chicago Seminars @ The Holiday Inn - The Original Points & Miles Event has hosted some of the best and brightest in the travel community. Through the years, thousands of attendees of all skill levels and from across the globe have convened at the Holiday Inn Chicago - Elk Grove to learn how to earn millions of points, public and secret tricks of the trade, and to travel like a jetsetter.

Although not the fanciest of venues, the Holiday Inn Chicago – Elk Grove is a wonderful place to congregate and treats us well every year. Plus, the hotel has an airport shuttle. We are excited to continue to call the Holiday Inn Chicago - Elk Grove home for another year.

While there are similar points and miles events, Chicago Seminars @ The Holiday Inn is unique in that it is a registered non-profit organization. ALL organizers are unpaid and all profits generated are donated to charity.

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To learn more, join the discussion in our Facebook group: Chicago Seminars @ The Holiday Inn - The Original Points & Miles Event.

Never attended an event like this? Make sure to read ​​​​SkiAdcock's “Thoughts & Tips” to learn how to make the most of your weekend.

For more than a decade, Chicago Seminars @ The Holiday Inn - The Original Points & Miles Event has created in-person connections which turn into meaningful and lifelong friendships across the globe. This weekend-long event will offer a mix of content for attendees at all levels. We look forward to you joining us and sharing your experiences at this Chicago homecoming.

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Lined Corporate SEO Optimization Scene
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Special Presentations

Up in The Air: A Fireside Chat with Tom Stuker, The World’s Most Frequent Flyer

Interviewer: Chris Moss

Chicago Seminars Then & Now: A Conversation with Rick Ingersoll, Founder of Chicago Seminars, and Howie Rappaport, Long-Time Organizer of Chicago Seminars

Interviewer: Marty Paz

How to Earn 492 Hyatt Elite Nights in One Stay: Million Baht Mindy (Mindy Davids) & One Year in the Hyatt Regency Bangkok

Interviewer: Chris Moss

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

Panel Discussions

Hardbody, The Plastic Merchant, Dogs with Credit Cards, and other Dumpster Fires: Deals Gone Wrong and Deciding When to Say No

Moderated by Kevin Song

Social Media & Groups: How to Use Them Effectively

Brandon Neth, Jackie Wisniewski, Senitra Horbrook, Shawn Coomer, Spencer Howard

Moderated by Julia Menez

Traveling as a Woman: Advice from Female Globetrotters

Panelists: Angel Trinh, Katie Genter, Senitra Horbrook, Tippe Morlan

Moderated by Ashley McCurdy



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

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 - Forbes Advisor 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 - Forbes Advisor


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

Tentative Schedule

Friday, October 13, 2023

4:00 PM: Registration Opens

5:30 PM: Opening Remarks

6:00 PM: Friday Night Sessions

8:30 PM: Reception (Two drinks included)

Saturday, October 14, 2023

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: Happy Hour

8:00 PM: Dinner (Not included)

Sunday, October 15, 2023

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)


AwardWallet is a one-of-a-kind service that helps you track all of your loyalty points including frequent flier miles, hotel points, dining rewards, and shopping rewards.

With helpful guides, lots of community input, and deal alerts in real time to help users know what cards to buy, where, and how: we think we’ve created a system that is easy enough for anyone to get started in the business and robust enough to be useful even for industry veterans.

TravelWise Advisors helps you travel smarter with better value - whether for business or for pleasure, using points or cash, or flying business class for the price of premium economy. Stop over in Istanbul on the way to Israel for no extra cost. Go on an African safari - for free. Cruise in a suite for the same price as a balcony room. It's all about value, and what's important to you. is the fastest search engine for award travel. Explore availability across entire regions, search with instant results, create free alerts and more to find the best flights for your points.

Typically, your cash back is limited to your everyday purchases. With QCGC, you can break through that ceiling. We specialize in buying gift cards, fuel points, concert tickets, and more. Our crowdsourcing model allows you to contribute as much or as little as you want, giving you an easy, guaranteed, and repeatable way to spend money on your credit cards, get reimbursed, and keep all

the points.


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

Tickets for the first 50 people who register are $160. After that, the price will increase to $175 until September 18, 2023, at which time all remaining tickets will cost $190. Additional discounts may be offered by speakers and sponsors of the event. Attendance is limited to 350.

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

There is a similar event occurring the same weekend which is not affiliated with Chicago Seminars @ The Holiday Inn, a registered non-profit organization.


Event tickets can be purchased via this link and include the following:

  • Access to all events at host venue (Holiday Inn Chicago - Elk Grove)
  • Lunch on both Saturday and Sunday
  • Two complimentary drinks at the Friday Night Reception
  • Coffee/tea throughout the event

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

Although registration is nonrefundable, registration is transferable for a $25 charitable donation and must be completed by Monday, October 9, 2023. Email if you would like to transfer a ticket.

Important Policies

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

  • Tickets are nonrefundable but are transferable for a $25 charitable donation
  • 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 $500 and can be personalized to suit any needs. Potential benefits include:

  • Promotional email to attendees sent via event email account
  • Complimentary registrations
  • Presentation opportunities
  • Sponsor table in lobby area
  • VIP event seating at every session
  • Access to Saturday Night Invite-Only After-Party
  • Opportunity to donate raffle prizes

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.

Hotel Information

Chicago O’Hare (ORD) is the closest airport to the event venue. The hotel runs a shuttle from ORD every half hour. Chicago’s Midway Airport (MDW) is extremely far but is accessible via public transportation with an expected travel time of 2 hours.

There are a limited number of rooms available at the venue for $129, which includes a continental breakfast. Once your ticket is purchased, the hotel booking link will be shared with you in the ticket confirmation email. Only ticketed attendees are allowed to reserve through this link or in the hotel room block. Each ticket holder can only reserve one room. If for some reason a person who has not registered for the event books within the hotel room block, the reservation will be canceled. Hotel rooms are on a first come, first served availability. The Hotel Booking Link will not work on the IHG app. Please use a desktop or mobile browsing app such as chrome.

Charity Raffle

Chicago Seminars @ The Holiday Inn raises thousands of dollars for charitable organizations through its Charity Raffle each year. 100% of these proceeds go to charity. In 2023, the selected charities are:


Airline Ambassadors International

Both travel- and non-travel-related items are being sought for the Charity Raffle. If you have items to donate, please email and 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.

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:

  1. 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 speakers’ content and allows open discussion of topics, some of which are intended to not be made public.
  2. 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.