Over the last couple of years, there have been two points and miles travel conferences taking place in Chicago during the Fall, each confusingly called “The Chicago Seminars.” For 2026, one of them, formerly known as “The Chicago Seminars: Heritage Edition,” will be changing its name to “The Chicago Points Travel Festival.”
This year’s get-together just wrapped up, and tickets for the 2026 festival are now on sale. The entire Frequent Miler Team will be there next year, so the organizers have kindly extended an Early Bird Registration discount code to FM readers.
The Deal
- The Presale for the 2026 Chicago Points Travel Festival (formerly Chicago Seminars Heritage Edition) has begun.
- Dates: October 16th-18th, 2026
- Location: Holiday Inn Chicago Oakbrook
- Cost: $299 per person
- Frequent Miler readers can get up to 20% off during the presale by using the promo code FM (Frequent Miler receives no compensation):
- $60 off for registrations through October 31st, 2025
- $40 off for registrations between November 1st and November 30th, 2025
- $20 off for registrations between December 1st and December 31st, 2025
- No discounts thereafter.
Direct Link to Registration Page (FM promo code automatically applied)
- Event tickets must be purchased and include the following:
- Admittance to programming, which begins Friday evening and runs all day Saturday and Sunday.
- Lunch on Saturday and Sunday.
- All-day coffee and tea on Saturday and Sunday.
- Two weekend drink tickets at the Holiday Inn bar.
- Fees for online registration.
- Other costs, such as name badges, supplies, etc.
There is no virtual option, and sessions will not be recorded.
Quick Thoughts
If you’re interested in expanding your knowledge in miles and points and honing your skills, attending a meetup like the Chicago Points Travel Festival can be a terrific investment. Not only does it provide more in-depth knowledge about earning and burning, it also gives you the opportunity to network with a larger community that’s into exploring points and miles as much as you are.
Nick often credits a conference that he went to years ago for opening his eyes to the possibilities of points and miles:
When I first got started in miles and points, I thought I had learned a lot and then I met a friend who told me about a conference like the Chicago Points Travel Conference.
My wife and I attended and my mind was blown because there were so many things I had been missing, despite having read blogs for some time. In fact, we learned so much at the first one we attended, that we flew across the country to attend another conference just a couple of months later.
Obviously how much you’ll learn will vary with the knowledge base with which you start and your comfort level in building connections with a new network, but even for those more advanced in the game I find these conferences especially useful for the networking. The Chicago conferences, in particular, often attract a crowd that is an interesting mix between beginners and people who have been in this game since before you thought the game existed.
After years of trying to make it happen, the entire Frequent Miler Team will be at the 2026 festival. This is the first time that we’ve ever been able to attend a points and miles meetup together, and we’re looking forward to it!
The complete lineup for 2026 is still being finalized, but you can find speakers and topics from the 2025 conference here.
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I got waitlisted, did they sell out or is everyone in the waitlist?
They sold out. They may be able to get room for another 50 attendees, and if they do, they’ll take those folks from the waitlist. I’ll update the post shortly.
Maybe someone will ask Stefan to supper in 2026 then.
I will fly from Japan for this!
Some people travel to see Taylor Swift in concert, but I’ll definitely travel to see the other TS (Tim Steinke) and FM team!!
Some people travel to see Taylor Swift in concert, I travel for the FM Team!
Man I would love to go but October is a no go due to business obligations. ☹️
Why is a points and miles festival being held at a mid 3* out in the burbs?
it more fun this way. hotel is very accommodating to the conference.
Conference rooms are expensive. Could hold at a more swanky place and ask participants to pay $500+
Oh – this sounds exciting! And I have an opening in my busy travel schedule! Should attendees plan on staying at the same hotel as the event? When do folks typically arrive/leave? I’ve always wanted to attend one of these, so maybe this will be the one! Thanks for sharing.
and I’ll likely get help figuring out what to do with my ~300k Wyndham points now that the Vacasa gig is dead!
So pleased that you all will be able to make it out next year! 🙂