I’ll be speaking at 2 travel rewards events this fall. If you love the wonderful world of free travel and want to become a real pro, I invite you to the most important event that’s designed for travelers like you (the other is really more for industry folks and isn’t relevant for most).
I invite you to join me and come meet me!
It always gives us great pleasure to talk to Flytrippers fans in person, as we often tell you. By the way, I have many other trips this fall (I have ~40 flights in total), so follow me on Instagram to see my stories in case we cross paths and can chat about travel.
Here are the details of the 2 events where I’m speaking.
Overview of the 2 events where I’m speaking
All the details are below, but here’s an overview.
Here are the 2 conferences with #1 being the most relevant for you to join as it’s the biggest and the most beginner-friendly:
- #1: Chicago Seminars Points Travel Conference
- For travelers (the major happening for 15+ years)
- Chicago, Illinois 🇺🇸
- October 24-26, 2025 (Friday to Sunday)
- Also included: 2 dinners + 2 drinks on Saturday’s 5-7 PM
- 219 USD (regular price; profits go to charity)
- 199 USD (with our link; sorry to charity)
- #2: Financial Affiliate Marketing Forum
- For industry (financial marketing)
- Toronto, Ontario 🇨🇦
- October 7, 2025 (Tuesday)
- Also included: Dinner
- 400 CAD (no discount available)
Chicago Seminars Points Travel Conference
Now in its 15th edition, the original cult event is one of the biggest, most popular, and oldest that exists. The Chicago Seminars is even the pioneering conference in the travel rewards world.
You should join if you really want to take it to the next level! If you want to attend just 1 event, this is really the one I recommend. It’s also more beginner-friendly, as there are multiple speaker tracks to choose from.
It’s an intensive weekend full of sessions where you’ll learn about all aspects of travel rewards, but especially where you’ll meet even more enthusiasts like you. There are always at least a few Canadians. And there are people of all ages!
With almost 30 different speakers, I’m sure plenty of topics will interest you. But it’s not intimidating at all; every time I’ve gone, it really feels like one big family, and it’s super relaxed.
Here are the logistical details:
- Friday, October 24 to Sunday, October 26
- From 5:30 PM Friday to 5 PM Sunday
- Optional additional day with masterclasses
- From 8 AM to 5 PM on Friday
- Separate ticket required at 99 USD
- Holiday Inn Chicago Oakbrook by IHG
- In the middle of Chicago’s endless suburbs
- Halfway between ORD and MDW airports
- Rooms available at 129 USD
- 199 USD with promo code FLYTRIPPERS20
- Applied automatically with our link
- Ticket available on Eventbrite
Let me know if you’re coming.
I wrote a detailed article about the Chicago Seminars if you want to learn more.
Financial Affiliate Marketing Forum
I’ve been attending the CardCon conference in the United States for several years. This year, there’s a sort of Canadian version of that conference, but it’s for financial marketing more broadly in Canada (instead of just for credit cards).
I’ll be hosting a panel for this first edition.
You shouldn’t join unless you work in the industry, honestly. It’s not designed for travelers or points fans at all, to be very clear.
Here are the logistical details:
- Tuesday, October 7, 2025
- From 8 AM to 5 PM
- The Quay
- Right next to Union Station
- Hundreds of accommodations around
- 400 CAD (no discount available)
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Summary
I’ll be speaking at 2 travel rewards events this fall, and I invite you to join me! Especially for the Chicago Seminars, as it’s one of the biggest events in the wonderful world of travel rewards and it’s designed for travelers who love free travel!
What would you like to know about the 2 travel rewards conference where I’m speaking? Tell us in the comments below.
See the flight deals we spot: Cheap flights
Discover free travel with rewards: Travel rewards
Explore awesome destinations: Travel inspiration
Learn pro tricks: Travel tips
Featured image: Session about Marriott in Chicago (photo credit: Andrew D’Amours/Flytrippers)
