Chicago Seminars

The Chicago Seminars were held again in mid-October, so we gathered with other fellow points and miles travelers in the Windy City (flying to and from on points and the Companion Pass of course). Believe it or not, we are not the only ones with this hobby.

Last year, Nick and Matt attended the actual conference, but this year a few more of us joined in on the fun craziness. There were about 500 attendees, plus many other travel speakers and bloggers.

The whole experience was fun, intense, and interesting all at the same time. These travelers are VERY passionate about this hobby and most of the conference circled around points, miles or other strategies. Although we have done our share of crazy (example being the 6 month stopover/layover that we are currently on), hearing some of these stories make us seem pretty normal. And yes, as you might imagine, one of my favorite sessions was the 1.75 hour Hyatt roundtable discussion. 

We went with the divide and conquer approach to hit almost every session between the five of us including:

Computer Tips and Tricks

Credit Cards

Managing Family Accounts

Alaska Airlines

Mileage Runs

Priceline and Hotwire

Southwest and the Companion Pass 

Award Bookings Asia

Award Bookings Europe

Special Award Bookings (one-ways, stopovers, open jaws)

ITA Software and Expertflyer

VRBO and AirBnBs

So basically the entire weekend was a learning and networking conference for travel enthusiasts. It is similar to the quarterly budget meetings these guys do on whatever financial topic(s), but this is like those meetings on steroids and involving purely travel. 

The weekend long conference is $85 which includes the sessions, lunch both days, beverages and snacks. It is a great event for networking and well worth the cost. There were many travelers from our local area there, so Matt may just be starting Flyertalk meet-ups back home now. Yes, the quarterly meetings might expand!

Personally, I enjoyed the Special Award Bookings session by Mile Value. It was extremely insightful when it comes to maximizing one-ways, stopovers, and open jaws. We are totally eyeing up New Zealand and the South Pacific in the near future, so it was good training to think outside of the box when booking award redemptions to high demand places with low award availability.

Overall though, my favorite session had to be the Spouse Session, a time for us +1s to get together and converse about travel over food, beverages and gift card giveaways while our points and miles crazy significant others were in session. It was relaxing and not so much focused on strategy, but rather on normal conversation with others like ourselves and the travel bloggers.

There was a Hilton DoubleTree a couple of minutes from the host hotel, so we stayed there for 10,000 points per night. The cookies were the highlight for the guys.

By Sunday afternoon, I was done talking miles and points and needed a break! We skipped out of the airline breakout sessions and round table discussions to experience a little of Open House Chicago with some of Kristina's friends. It is a free weekend event where 150 buildings are opened up to the public. There are some pretty sweet places and companies on the list, and I wouldn't mind spending an entire weekend next year to explore some of these buildings. 

First stop was Goose Island Beer Company for a self-guided tour and complimentary craft brews.

Then, we went downtown for a little while to check out a few other sights.

Nick capturing some of our points and miles favorite things: swag bags and Chase branches. 

The Board of Trade was at capacity already, so we ventured across the street into the Chicago Fed.

We tried to hit a few others sights like the Chicago Temple and MDA City Apartments (which looked sweet and had rooftop access!), but they were turning away visitors by that point.

M and I left the rest of the group to catch our evening flight (the others were flying out in the morning), but could not resist a stop at Magnolia Bakery on our walk back to the car.

Husband approved of a treat since I had behaved well this weekend. The pumpkin cupcake with cream cheese frosting was calling my name.

Until next time Chicago.