3 travel rewards conferences where I’m speaking this fall

I’ll be speaking at 3 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 of the 2 events that are 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 (the 1^st is this weekend, but it’s the 2^nd that’s more beginner-friendly and it’s almost sold out)!

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 3 events where I’m speaking.

Overview of the 3 events where I’m speaking

All the details are below, but here’s an overview.

Here are the 3 conferences, with the 2 where it’s relevant for you to join listed first:

• Pacific Northwest Points Travel Festival
  • For travelers (smaller and less beginner-friendly)
  • Vancouver, British Columbia 🇨🇦
  • September 19 and 20, 2025 (THIS Friday and Saturday)
  • Also included: Friday picnic + Saturday dinner
  • 199 CAD (regular price)
  • 179 CAD (with our link)
• 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)
• Financial Affiliate Marketing Forum
  • For industry (financial marketing)
  • Toronto, Ontario 🇨🇦
  • October 7, 2025 (Tuesday)
  • Also included: Dinner
  • 400 CAD (no discount available)

Pacific Northwest Points Travel Festival

It’s the organizer of the next event below who’s behind this one, but it’s a really smaller and more informal conference than the other. Even if it’s in Canada, it’s really more for pros.

Despite the Vancouver location, it’s also focused on US-issued cards (which you should really get too, even as a Canadian, if you want to be serious in this wonderful world; don’t miss our special guide very soon).

It actually started as a meetup for the entire points enthusiast community in the Pacific Northwest region. It attracted fewer people from outside, but it’s opening up a bit more this year, and all travelers from everywhere are certainly still welcome.

There’s a free picnic on Friday evening (I’m missing it because I have another conference to meet with many banks in Toronto on Friday) and a full day of sessions on Saturday, with about a dozen speakers.

It’s a great excuse for a visit to Vancouver, which is always enjoyable. You have Sunday free to explore if you want.

Here are the logistical details:

• Friday, September 19 and Saturday, September 20, 2025
  • From 5 PM Friday to 5 PM Saturday
• Creekside Community Recreation Centre
  • Right next to downtown
  • Hundreds of accommodations around
• 179 CAD with our Flytrippers link code
  • Applied automatically with our link
  • Ticket available on Eventbrite

Don’t hesitate to let me know if you’re coming.

But I honestly recommend the next conference more.

Chicago Seminars Points Travel Conference

Now in its 15^th 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 of the 2, 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’s 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, too, if you’re coming.

I wrote a detailed article about the Chicago Seminars if you want to learn more.

Learn more

Chicago Seminars Points Travel Conference 2025: An invitation to meet me in October

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 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)
  • Ticket available on Eventbrite

Learning how to travel for less

Join over 100,000 savvy Canadian travelers who already receive Flytrippers’ free newsletter so we can help you travel for less — including thanks to the wonderful world of travel rewards!

Summary

I’ll be speaking at 3 travel rewards events this fall. The first 2 are designed for travelers who love free travel, 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.

What would you like to know about the 3 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)