Advertiser Disclosure: Eye of the Flyer, a division of Chatterbox Entertainment, Inc., is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as CreditCards.com. Some or all of the card offers that appear on the website are from advertisers. Compensation may impact how and where card products appear on the site. This site does not include all card companies or all available card offers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed, or approved by any of these entities. Some of the 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.

I love the windy city. I love the vibe, the food, Navy Pier, Segway rides along the lake shore, the architectural boat rides, the Hancock tower for brunch, the view from the top of the “Sears” tower (yeah, we still call it that), shopping at IKEA, all sorts of sports teams, oh and one more amazing thing that comes around each year:
The Chicago Seminars for frequent flyer junkies. I have been attending since the very first one and have been speaking at them for a number of years. I love this event.
But who should go, what is it all about, and will it be too much for me or too little for me? What if I am a super newbee or I am a seasoned pro. Will I feel overwhelmed or bored? Let me show you what it is like.

- Angelina from Angelina Travels
- Chris from ExpertFlyer
- Dan Miller from Points with a Crew
- Daraius from Million Mile Secrets
- Dave aka Bikeguy of FlyerTalk
- Drew from Travel is Free
- Emily from Million Mile Secrets
- Howie from Award Wallet
- Jen from Deals We Like
- Miguel from PMMTravelConsulting
- René from RenesPoints
- Scott from MileValue
- Shawn from Miles to Memories
- Stefan from Rapid Travel Chai
- Tiffany from One Mile at a Time
You will have the chance to learn in either large or smaller sessions on topics we all want to learn about as well as:
Break out rooms for more targeted focused travel topics as well as airline breakout sessions. The first time I went I thought my head was going to explode because there was so much information to take in. Does that mean someone new should not go? Far from it. If you are new this is THE event to attend as no one will make fun of you for being new or asking any question. We are there to share and help. Come up and talk to any of the speakers and you will see what I mean. Please come up and talk to me. Like where?
Like the bar attached to the Holiday Inn Hotel Shelby Campbell’s. This is where we tend to hang out for most of the weekend when not in a session speaking.

You may even have a chance to sit down and talk to a legend in the game, that is, Rick Ingersol the founder of Frugal Travel Guy. Rick is amazing and I never get sick of hearing him speak. He knows points inside and out.
So what if you are a pro? Should you still attend? I know a bunch of folks who seem to know everything about the frequent flyer “hobby” but they still come. Some of them hardly go to any of the sessions but just hang out and have fun and pick up a tip or two from old friends that make the entire weekend worth the effort. All it takes is one great tip to change the way you play the game. Heck, if you live in Chicago just come by the bar and chat a bit! 😉
Some other important tips. Get their early on Friday the 14th of October! If you want to hear me speak you need to be there well before 5 PM on Friday when the event kicks off. I will be talking about Mileage Runs first and then followed by an introduction to creative spending as well as some warnings and tips.
Saturday I will just be around so come find me (hint, check Shelby Campbell’s) or somewhere else like helping out at check-in or in the common area of the hotel. Keep in mind we book the entire Holiday Inn so it is all just “us” all weekend long.
It seems, as always, the host hotel is sold out. But here is a tip, try calling. Sometimes they are not fully sold out but the web site says they are. Also, if they are totally sold out, don’t despair. Each and every year, days before the event, a few rooms open up so just HUCB each day before the event until you get a room! If you are an SPG fan there is a Sheraton Suites just a short drive or Uber away from the host hotel and it is cheap on points and has a nice club lounge.
How to get there. Fly to ORD (don’t do MDW it is too far away unless you rent a car). There is a free airport shuttle and if you are a Delta flyer yes, there is a Sky Club at ORD for you to enjoy!
So there you have it folks! You can buy your tickets here (before they sell out). I am stoked about this year’s event and can’t wait to see old friends and hopefully meet new ones as well. – René
Advertiser Disclosure: Eye of the Flyer, a division of Chatterbox Entertainment, Inc., is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as CreditCards.com. Some or all of the card offers that appear on the website are from advertisers. Compensation may impact how and where card products appear on the site. This site does not include all card companies or all available card offers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed, or approved by any of these entities. Some of the 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.
Responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.
I agree, the Chicago Seminars are well worth the time and (relatively minor) expense. I’ve been to several, and have never failed to learn new tricks and techniques of the miles & points game. The energy level is high, and it’s the only place where everyone around you understands what you are talking about.
Is there anything like this on the west coast?
@Susan – There are FTU events. https://ftuniversity.com/
I’m really looking forward to coming back for my second year. Perhaps I’ll actually say hi this time.
It’s my first Chicago Seminar and looks like I’ll do it as a yearly event!
Sad I missed the last two years but hey, better late than never.
Will be great to meet new folks and learn new things from this hobby! I was actually surprised at how affordable the ticket is for 2 1/2 days of events!
@Ruby – I think this is year 5 🙂
Some other things to do in additional to Rene’s list are Eataly Mario Batali’s giant Italian Food Emporium and the Riverwalk where you can watch boats cruise by while enjoying a glass of wine.