Chicago Seminars Go Virtual In 2020

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In 2009, one of the premier ‘miles and points’ events was held at the Holiday Inn in Elk Grove, Illinois (near Chicago O’Hare Airport) called the Chicago Seminars.

Ten years later, the annual event is still going strong and an opportunity for novice and pros to mix and mingle, brag (in a good way) about their latest travel adventures, and discuss secrets that are rarely disclosed on the web.

Although I did not attend the inaugural Chicago Seminars, I’ve been an attendee for several years and each time feels like a mini-family reunion as you’re able to connect with your favorite travel bloggers and also expand your inner circle with other miles and points enthusiasts.

In fact, the idea to blog about my solo and family adventures using miles and points was born out of a conversation with Tiffany Funk at OMAAT while at the seminars.

Unfortunately, 2020 has thrown a wrench into many aspects of our lives, including the Chicago Seminars, but there’s good news.

The 11th Annual Family Reunion (aka the Chicago Seminars) will be taking place virtually as an online “Variety Show” this coming Saturday, 17 October 2020.

Stefan Krasowski of Rapid Travel Chai describes the virtual meet-up as follows:

This will not be a virtual “conference”. Rather it will be a telethon with one surprise guest after another. Very live, very chaotic, people popping in and out, with a mix of Q&A with me and other guests, a few slots with speakers sharing rapid-fire on a topic, and a generally high-energy event.

The livestream event will include an assortment of speakers, including:

  • Tiffany Funk
  • Dia Adams
  • Matthew Klint
  • Howie Rappaport & Rick Ingersoll
  • Nick Reyes & Stephen Pepper
  • Shawn Coomer & Mark Ostermann
  • Dave Homyak
  • Thomas Carnevale
  • Zachary Finkelstein
  • Henning Mente
  • Marty Paz & JJ Todd
  • Jamal Robinson <—…started at the bottom, now we’re here!! 😎
  • …and a variety of “celebrity” cameos 😉

The “kick-off” which will be held Thursday (15 October) from 7-8 pm (EST). The public livestream – A Decade of Chicago Seminars – will be hosted by Stefan Krasowski on Youtube and is free of charge to all.

Tickets to the main event (17 October) are just $11 with proceeds going to charity. To register for the event, simply CLICK HERE.


Let’s be honest, there’s no replacing the actual vibe and exposure of the in-person event.

Personally, I’m an “early to bed, early to rise”- type person but at this event, all of that disappears. I’ve found myself on several occasions hanging out at the social events, happy hours, and in the hotel lobby into the wee hours of the morning discussing points and miles.

As mentioned above, the crowd generally consists of a good mix of “newbies” and “pros” alike, so if you’re looking to go a bit deeper with miles and points, join us as I trust this event will definitely inspire.

Will I see you (virtually) at the Chicago Seminars?

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