The Chicago Seminars Points Travel Conference is one of the longest-running events in the world of travel rewards. I will be on panels and presenting a few talks at the 15th edition from October 24-26, 2025. So I wanted to invite you if you want to meet me to talk about travel, or if you want to just spend a cool weekend learning and networking with many travelers who share your passion.
Another option is a new points event happening in Vancouver where I’ll be speaking too, in September. Sign up for our free newsletter to receive the official invite in the next few weeks.
I was a speaker at the Chicago Seminars for the last 2 years and am glad to return to this event, which is always a fun one. It was the very first points event I participated in back in 2017, and I met so many cool travelers.
(If you want to meet up to talk about travel somewhere else, I love running into Flytrippers followers and I’ll also be at my 3 other American annual fall destinations at the When We Were Young Festival in Vegas the week before, in New Orleans at a date to be determined, and at Miami Art Week at the usual dates in December!)
Here are the details of the Chicago Seminars Points Travel Conference 2025.
What is the Chicago Seminars Points Travel Conference?
For 15 years, the Chicago Seminars have been arguably the main conference about travel rewards.
It’s often called “the original miles and points conference” and prides itself on being by the points community and for the community. It has great, knowledgeable speakers and also great attendees with whom to make friends. It’s a really down-to-earth event, and the crowd is not at all formal or uptight.
It’s a not-for-profit event with all proceeds going to charity. Event staff and speakers — like myself — are all volunteers, although we do get (partial) reimbursement for travel expenses only.
Confusingly, as of recently, there are now 2 different travel rewards conferences, both called Chicago Seminars, and both claiming the event’s past history. This is due to an unfortunate conflict between organizers that sadly could not be resolved. The Chicago Seminars I’m speaking at is the one that is in October on the usual dates. The other one takes place in November.
When is the Chicago Seminars Points Travel Conference 2025?
The 2025 event takes place from Friday October 24 at 6 PM to Sunday October 26 at 5 PM. It’s a whole weekend of points and miles fun.
There’s also something new this year: Masterclasses are offered earlier on Friday during the day for those arriving before the evening (ticketed separately). I will lead a Canadian-focused masterclass along with Moli of Maple Miles.
Where is the Chicago Seminars Points Travel Conference 2025?
In Chicago. Okay, you probably had figured that part out.
It’s actually in the Chicago suburbs, at the Holiday Inn Chicago Oakbrook, an IHG hotel renovated in 2024. It’s approximately halfway between Chicago–O’Hare (ORD) and Chicago–Midway (MDW) airports. While the hotel doesn’t have a free shuttle, group transportation options are in the works.
You can book a room for US$129 as part of the conference if you wish to stay at that hotel (you’ll get the instructions once you buy the ticket).
Or, if you need Marriott nights for elite status like me, there’s the Chicago Marriott Oak Brook, about a $10 Uber away. I’ll probably be there and we’ll be able to carpool, haha!
If you’re loyal to other chains, the closest Hilton is either the DoubleTree by Hilton Hotel Chicago – Oak Brook, or the Hilton Garden Inn Chicago/Oakbrook Terrace. The closest Hyatt is the Hyatt Place Chicago/Lombard/Oak Brook (or the Hyatt Lodge Oak Brook Chicago, which is one of the rare standalone Hyatts, which helps for the brand explorer feature).
How do I buy tickets to the Chicago Seminars Points Travel Conference 2025?
You can buy a ticket for US$219 on Eventbrite. The event fee is non-refundable but is transferable to someone else for US$50 before October 18.
The ticket includes all sessions, coffee/snack breaks, 2 free drinks at the Saturday Happy Hour, and both lunches.
Breakfast is included for those who book the room block. Dinners are not included, but these are usually a great way to make new friends and branch out into smaller, more intimate groups, as the area has great restaurants for deep-dish pizza or Polish pierogi.
Who is the Chicago Seminars Points Travel Conference 2025 for?
Anyone who wants to take their travel rewards knowledge to the next level.
The conferences themselves are amazing, but the most important part is the networking and getting to know other travelers who also love getting free travel.
What is it like to attend the Chicago Seminars Points Travel Conference 2025?
It’s a very approachable event, not formal at all; it’s really like being among a big group of friends. It has the greatest age group variety that I’ve seen at a points event.
The sessions and talks really do cover almost everything you’d want to know about travel rewards. There are usually at most 2-3 session tracks at the same time, so you don’t normally have too many conflicting topics during the weekend. The event is also known for its panels where the speakers, all experienced travelers and experienced points and miles enthusiasts, discuss various topics.
And the attendees have very varied backgrounds as well. While a vast majority are American, I found it easy to mingle and bond over the common passion of travel the year I went as an attendee and not a speaker.
And you’ll learn so much about travel in general, too — not just travel rewards. For example, in 2023, we even got to hear from Tom Stuker, the world’s most frequent flier (he has flown 24 million miles; that’s about 1,000 times around the world).
Who is speaking at the Chicago Seminars Points Travel Conference 2025?
Apart from me, there are over a dozen other interesting speakers who are sure to cover topics that are of interest to you. My topics — along with everyone else’s, obviously — will be announced very soon, and I’ll update this post accordingly.
Here are the other speakers:
- Me
- Stefan Krasowski (Rapid Travel Chai)
- Mindy Bumgarner (MS FIRE)
- Chris Carley (Eye of the Flyer)
- Shabbir Hakim (cardZTravel)
- Andy Hicks (everycountryby50)
- Dave Homyak (bikeguy)
- Aaron Hurd (PointsAndTravel)
- Chris Hutchins (All the Hacks Podcast)
- Lucy Hsu (Every Passport Stamp Facebook Group)
- Kathy Kass (Will Run for Miles)
- Ben Komenkul (Ben’s Big Deal)
- Linda Lay (SoloPear Travel)
- Moli (Maple Miles)
- Julia Menez (Geobreeze Travel Podcast)
- Dawn Royski (Share Traveler)
- Justin Vacula (Hurdy Gurdy Travel Podcast)
- Rachel Yuan (Prince of Travel)
- Sarah Ramkissoon
- Andrew Derthick
- Amy M. Gardner
Is the Chicago Seminars Points Travel Conference 2025 recorded for replays?
No, and it’s actually one of the event’s only rules; you can’t record any of the content yourself, either.
Some speakers will discuss tips and tricks that are better kept private, and they prefer not to have a public trace of them in any shape or form.
How can I learn more about the Chicago Seminars Points Travel Conference 2025?
The event’s longstanding organizer, Stefan Krasowski, did a 1-hour podcast interview about the event.
If you have a great memory, you might remember that Stefan had invited me to chat about my quest to visit every country in the world (which he has already accomplished himself).
That’s not the main focus of the Chicago Seminars, as most people are “normal” travelers and want to use their points for more normal aspirations. But you can definitely learn about more extreme travel while you’re there if you’re so inclined. And especially about how much easier it is to visit every country in the world thanks to travel rewards.
How to get to the Chicago Seminars Points Travel Conference 2025?
There are many routes to Chicago-O’Hare (ORD), being the world’s 9th busiest airport. Chicago-Midway (MDW) often has cheaper fares, too.
You can read our introduction to 31 tips to save on plane tickets and try out one by one all those that apply to your situation.
What else can I do in Chicago?
Chicago is such an amazing city, but you won’t get to see any of it if you come in just for the event. I’d highly recommend staying at least an extra day, if you can, to at least get to explore the city a bit.
I’ll share my experience in Chicago in a post soon; stay tuned.
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Summary
The Chicago Seminars Points Travel Conference is happening from October 24 to 26, and I’ll be giving a few talks again this year, along with some other great speakers. Whether you’re looking to up your knowledge of travel rewards or connect with fellow travel enthusiasts, consider joining me at this fun event.
What would you like to know about the Chicago Seminars Point Travel Conference? Tell us in the comments below.
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Featured image: Chicago Seminars Points Travel Conference (photo credit: Andrew D’Amours/Flytrippers)
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