Advertiser Disclosure: Eye of the Flyer, a division of Chatterbox Entertainment, Inc., is part of an affiliate sales network and and may earn compensation when a customer clicks on a link, when an application is approved, or when an account is opened. This relationship may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed, or approved by any of these entities. Some links on this page are affiliate or referral links. We may receive a commission or referral bonus for purchases or successful applications made during shopping sessions or signups initiated from clicking those links.
The Chicago Seminars Heritage Edition will return in 2026. Except for one kinda big detail.
Due to a lot of behind-the-scenes happenings (some might call it unnecessary and avoidable drama), there have been two separate events called the Chicago Seminars since 2023.
The Chicago Seminars Heritage Edition — helmed by a Stefan Krasowski-led group — just wrapped its 2025 weekend at the Holiday Inn Chicago Oakbook. (The “15th Annual Chicago Seminars – The Original Points and Miles Event” has its event on November 7-9.)
The Chicago Seminars Heritage Edition now becomes the “Chicago Points Travel Festival.” Next year’s event takes place Friday, October 16, through Sunday, October 18, 2026. It returns to the Holiday Inn Chicago Oakbook. (Worth noting: there’s a Dunkin’ less than a five-minute walk from the hotel. Great for us American Express® Gold Card members!)
Registration is live now. Standard admission is $299. However, use password/code “EYE” for a special early bird discounts:
- From October 28 to 6:00 AM Eastern Time on November 1, save $60
- From 6:01 AM Eastern on November 1 to November 30, save $40
- After that, save $20 through December 31
Speakers/presenters, etc., will be announced at some point. The 2nd Hyatt Lodge Fun Run/Walk also takes place that weekend as part of the event.
Rooms at the host hotel will cost $139/night + tax, and include breakfast for one adult. Rooms should be available for booking sometime next month.
THANK YOU to everyone who attended my presentations and/or introduced themselves this past weekend! I enjoyed seeing everyone and hope you enjoyed the event.
Advertiser Disclosure: Eye of the Flyer, a division of Chatterbox Entertainment, Inc., is part of an affiliate sales network and and may earn compensation when a customer clicks on a link, when an application is approved, or when an account is opened. This relationship may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed, or approved by any of these entities. Some links on this page are affiliate or referral links. We may receive a commission or referral bonus for purchases or successful applications made during shopping sessions or signups initiated from clicking those links.










Great news! I will be there.
me too!!
I will try to attend.