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The Chicago Seminars were last Friday through Sunday just outside O’Hare at the Holiday Inn Elk Grove. I had an absolute blast, learned quite a bit, and highly recommend everyone go next year. This post is part recap, part tips for next year if you go. Interspersed are pictures of me and some of my favorite bloggers.

Daraius (Million Mile Secrets) and I are both in our signature outfits

I had volunteered to help with registration starting at 4 PM on Friday. I got to the hotel at 2 PM because I was so excited to meet people whose writings I’ve been following. As I walked to the hotel, I noticed that it was across the street from an Office Depot–famous in the miles community for selling Vanilla Reload cards. See my post on the AMEX Reloadable/Vanilla Reload bonanza.

I tweeted Frequent Miler, the king of reloads, and he said he and Ben from One Mile at a Time had already done a reconnaissance mission and determined there were no Vanilla Reload cards. No big deal, we’ve got them in LA, and they wouldn’t have lasted long with all of us next door.

Mommy Points–who’s sassier?

I brought an Economist in case I was the first to arrive, but I didn’t open it before I met a fellow attendee. Pretty quickly we had six or seven of us gathered and talking miles. Rick (Frugal Travel Guy), Stefan from Rapid Travel Chai, and Scott (Hack My Trip) were a part of that conversation with many more joining in as the airport shuttle arrived every thirty minutes.

Time flew, and before I knew it, I was five minutes late for my volunteer shift setting up for the registration. I was happy to volunteer because one really cool thing about the Seminars is that all proceeds not spent on booking the conference rooms, paying speakers’ travel costs, lunch, and drinks are donated to charity.

Howie (Frugal Travel Guy) coordinated, and I met Stacey (Very Good Points) and Rene (Delta Points) who were also stuffing name tags and handling check in.

Ben (One Mile at a Time)–one of the few attendees younger than me

At 5 PM, Frequent Miler and I had a dinner planned that we set up months ago. We were joined by Mommy Points, Rick, and his wife. The first Seminars started after our dinner wrapped up. At 8:30, when the program ended, Parag (Frequent Flyer University) and I hosted our readers in the hotel bar. I had a few drinks to buy.

It seems like most readers cleared out by 11 to get a good night sleep for the upcoming information overload. But in the back corner, I found Brian (The Points Guy), Ben (One Mile at a Time), Scottrick, Stefan, Howie, and more having a few drinks.

Frequent Miler is 6’0″, but I’m on my tip toes

The next morning began a full day’s worth of amazing knowledge transfer. My favorite talk was from Captain Denny–a United pilot. Captain Denny became “famous” in the frequent flier community for being the pilot with the best imaginable customer service. Here’s one of many articles about him.

A lot of my friends are comedians, so I recognized his talk for what it was: a stand up comedy routine. Set up, punch; set up, punch. It was absolutely hilarious, but also heartwarming at times and inspiring throughout. If we all did our jobs the way Captain Denny does his, everyone would be quite a bit happier.

Brian (The Points Guy)–thirteen feet of bloggers

Saturday night featured free drinks after the program. Attendees had one hour to drink 600 drinks, so The Points Guy’s team–in matching t-shirts–was giving out the free coupons freely.

During Sunday’s lunch, I ate with the Mr. Pickles. After lunch, there was a blogger Q & A session with about 15 bloggers answering pre-written and live-audience questions moderated by Rick. I had to leave about half way through to catch my flight back to LAX. I left a few minutes before a tornado warning went off at the hotel apparently.

Steve (Beaubo) is Gary Leff’s award-booking partner, and the non-blogger I most wanted to meet.

Overall the Seminars were informative and entertaining. I met a ton of bloggers, readers, and other miles enthusiasts. And every one of them told me something I didn’t know. There are a few tricks and techniques I am eager to put into practice, research, and write about. I am 100% certain I’ll return next year, and I have a few tips if you’ll be joining me. I’ll reprint these next year, but I want to write them while they’re fresh in my mind.

Rick (Frugal Travel Guy)–without him there would be no Chicago Seminars. Thanks for everything, Rick.


The hotel is a few miles from O’Hare and 20+ from Midway, so O’Hare is the obvious choice. But if you want to see the city at all, you might want to consider doing what I did: flying into Midway and out of O’Hare.

I flew into Midway on Southwest on Thursday afternoon. The Orange line of the L goes from the airport to downtown. I took my brother’s advice for a 90 minute walk since he lived in Chicago for several years.

That allowed me to spend the afternoon exploring Chicago. I walked down Michigan Avenue from the Clark/Division L stop to Jackson-Blue. That’s a great route with beautiful sites and crosses the river.

Then I left from O’Hare, so I could leave as late as possible. Next year, I’ll make sure I leave even later, so I can see all of the Seminars.


The most convenient option is the Holiday Inn Elk Grove where the conference is. It was also reasonably priced at $99 per night, but I wanted something cheaper. I wasn’t going to rent a car, so I looked for the cheapest hotel in walking distance from the Holiday Inn on Google Maps and I found the Days Inn 0.9 miles away for $52/night. I stayed there Thursday and Friday nights.

Saturday night, I moved to the Radisson O’Hare that was 3.9 miles from the Holiday Inn. I had to use taxis, but it allowed me to get in on the Stay One Night, Get One Night Free promo.

Unless you want the convenience of staying at the Holiday Inn, I recommend waiting for the last minute to book to see what hotel promos are out there for mattress running.


A buffet lunch is included in the ticket price. A breakfast buffet is included in your room’s price, or you can purchase it separately. I ate dinner both nights at the attached restaurant, which was reasonably priced.

Other options include the Panda Express and Starbucks across the street from the Holiday Inn.


Friday afternoon and Sunday, the Holiday Inn’s shuttle was running every thirty minutes to O’Hare. If you don’t want to wait, you don’t have to. There are probably several Chicago Seminar attendees standing near you waiting. Ask them to split a cab, which is probably under $15 with tip.

If you are coming from the city, take the Blue line to O’Hare. The station is almost directly under the hotel-shuttle pick up area.


I really enjoyed volunteering. I enjoyed meeting the other volunteers and helping out. I responded to a volunteer request on the Frugal Travel Guy’s site last month. I think there was also one on the FlyerTalk thread. You can volunteer for an hour or two.

People show up all day Friday, so don’t be afraid to get there early.

If you want to meet someone, go introduce yourself. Everyone is friendly and approachable, but some people are introverted, so make the first move.

The hotel bar made the mistake of offering one cent beers to those who checked in on Four Square when a deal-obsessed horde was in town. The only cheaper drinks were those being offered by me for free to readers who had responded to my secret message a few weeks before the event. I might do something similar next year.

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